TRIPHENYLPHOSPHANE

Triphenylphosphane is a white crystalline organophosphorus compound widely used in organic chemistry.
Triphenylphosphane is soluble in many organic solvents but insoluble in water.
Triphenylphosphane is recognized for its role as a ligand and its ability to form stable complexes with transition metals.

CAS Number: 603-35-0
EC Number: 210-036-0
Chemical Formula: C18H15P
Molecular Weight: 262.29 g/mol

Synonyms: Triphenylphosphane, PPh₃, Triphenyl phosphorus, Phosphine, triphenyl-, TRIPHENYLPHOSPHINE, 603-35-0, Triphenylphosphane, Triphenyl phosphine, Phosphine, triphenyl-, Triphenylphosphorus, Triphenylphosphide, triphenyl-phosphane, Phosphorustriphenyl, Trifenylfosfin, triphenylphosphin, Phosphorus triphenyl, PPh3, PP 360, NSC 10, Ph3P, CCRIS 4889, NSC 215203, DTXSID5026251, triphenylphosphan, HSDB 4266, EINECS 210-036-0, triphenylphosphorane, triphenyl phosphorus, BRN 0610776, NSC-10, UNII-26D26OA393, MFCD00003043, 26D26OA393, NSC-215203, DTXCID906251, CHEBI:183318, EC 210-036-0, 4-16-00-00951 (Beilstein Handbook Reference), triphenylphoshine, WLN: RPR&R, Trifenylfosfin [Czech], MFCD20489348, TRIPHENYL PHOSPHOROUS, CAS-603-35-0, C18H15P, Triphenyl phosphine resin, 14264-16-5, triphenyphospine, tripenylphosphine, triphenyiphoshine, triphenylphophine, triphenylphospine, tripheylphosphine, Triphenylphospane, Triphenyphosphine, tripbenylphosphine, triphenyiphosphine, tri-phenylphospine, triphenyl phophine, triphenyl phosphin, triphenyl phospine, tri-phenylphosphine, triphenyl phosphide, triphenyl-phosphine, triphenylphosphine-, triphenyl- phosphine, 58079-51-9, Triphenylphosphine, 98%, Triphenylphosphine, flakes, Triphenylphosphine, powder, Diphenylphosphinopolystyrene, SCHEMBL101, (Ph)3P, P(Ph)3, NSC10, Triphenylphosphine 1M in THF, TRIPHENYLPHOSPHINE [MI], SCHEMBL1679860, P 100 (ACCELERATOR), CHEMBL1448331, TRIPHENYLPHOSPHINE [HSDB], (C6H5)3P, BCP01148, P(C6H5)3, Tox21_202114, Tox21_303294, NSC215203, STL185621, AKOS009031542, Triphenylphosphine, >=95.0% (GC), AT26025, FT48242, NCGC00091416-01, NCGC00091416-03, NCGC00257211-01, NCGC00259663-01, BP-12577, Triphenylphosphine, ReagentPlus(R), 99%, DB-050422, Bis(triphenylphosphine)nickel(II)dichloride?, NS00002889, T0519, EN300-19636, A15679, Triphenylphosphine, ReagentPlus(R), >=98.5%, Q115493, F1642-0085, Triphenylphosphine polystyrene (200-400 mesh, 0.8-1.5 mmol/g), 210-036-0, FPZ, InChI=1/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15, JandaJel(TM)-triphenylphosphine, 50-100 mesh, extent of labeling: ~3.0 mmol/g P loading, 2 % cross-linked, triphenylphosphine;phosphine, triphenyl-;triphenylphosphane;triphenyl phosphine;triphenylphosphine phosphine, triphenyl- triphenylphosphane triphenyl phosphine, 210-036-0, 4-16-00-00951, 58079-51-9, 603-35-0, MFCD00003043, Ph3P, Phosphine, triphenyl-, Phosphorustriphenyl, Trifenylfosfin, Triphenyl phosphine, Triphenylphosphan, triphenylphosphane, Triphenylphosphin, Triphenylphosphine, Triphénylphosphine, 112771-47-8, 13965-03-2, 24762-44-5, 99%, MFCD00148025, MFCD20489348, PHOSPHORANE, TRIPHENYL-, Phosphorus triphenyl, RPR&R, tpp, tri(phenyl)phosphane, TRI(PHENYL-D5)PHOSPHINE, Trifenylfosfin, triphenyl phosphorane, Triphenyl phosphorous, triphenyl-phosphane, Triphenylphosphan, Triphenylphosphide, Triphenylphosphin, Triphenylphosphine, flakes, Triphenylphosphine, polymer-bound, on styrene-divinylbenzene copolymer (20% cross-linked), TRIPHENYLPHOSPHORANE, TRIPHENYLPHOSPHORUS, 三苯基膦

Triphenylphosphane is a fundamental chemical used in a variety of laboratory and industrial applications.
Triphenylphosphane serves as a versatile reagent in organic synthesis, playing a vital role in reactions such as the Wittig reaction for alkene formation and the Mitsunobu reaction for the conversion of alcohols.
Its strong nucleophilic character and ability to act as a Lewis base make it an essential component in homogeneous catalysis systems involving transition metals such as palladium, platinum, and rhodium.

Triphenylphosphane can form stable adducts with a variety of electrophilic reagents, and upon oxidation, it yields Triphenylphosphane oxide, an important by-product in many synthetic processes.
In terms of physical properties, Triphenylphosphane is a white to slightly off-white crystalline solid, odorless, with a melting point of 79–83°C and a boiling point of approximately 377°C.
Triphenylphosphane is moderately dense (about 1.19 g/cm³) and shows high solubility in non-polar solvents such as benzene and toluene.

Industrial production of Triphenylphosphane involves the reaction of phosphorus trichloride with chlorobenzene in the presence of sodium metal, producing Triphenylphosphane along with sodium chloride as a byproduct.
Careful control of moisture and oxygen exposure is necessary to maintain product purity during storage and handling.

Triphenylphosphane finds extensive use not only in chemical synthesis but also in the stabilization of polymers, production of pharmaceuticals, agrochemicals, and the development of advanced material systems.
Triphenylphosphane's environmental persistence is moderate, but its oxidation products require proper management to avoid ecological impact.

Triphenylphosphane is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
Triphenylphosphane is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Rhodium and Triphenylphosphane catalyst system has been used for the hydroformylation of soybean, safflower and linseed oils and their methyl esters.
Polymer supported Triphenylphosphane has been reported to efficiently catalyze the γ-addition of pronucleophiles to alkynoate.

Triphenylphosphane reacts with hydrated ruthenium trichloride in methanol to afford [RuCl2(PPh3)4], [RuCl2(PPh3)3] and [RuCl3(PPh3)2CH3OH].
Triphenylphosphane participates in the Heck reaction of 4-bromoanisole and ethyl acrylate in ionic liquids.

Triphenylphosphane is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P.
Triphenylphosphane is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry.

Triphenylphosphane exists as relatively air stable, colorless crystals at room temperature.
Triphenylphosphane dissolves in non-polar organic solvents such as benzene and diethyl ether.

Triphenylphosphane is a member of the class of tertiary phosphines that is phosphane in which the three hydrogens are replaced by phenyl groups.
Triphenylphosphane is a member of benzenes and a tertiary phosphine.

Triphenylphosphane is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character.
Triphenylphosphane is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds.

As a reducing agent, Triphenylphosphane is used to prepare aromatic amines from the corresponding aromatic N-oxides.
Triphenylphosphane is also used to prepare Wilkinson's catalyst.

Triphenylphosphane is an organophosphorus compound with the chemical formula C18H15P, consisting of a phosphorus atom centrally bonded to three phenyl groups.
Triphenylphosphane appears as a white to slightly off-white crystalline solid that is odorless and highly soluble in many organic solvents such as benzene, chloroform, and ether, but insoluble in water.

Known for its strong nucleophilicity and mild reducing properties, Triphenylphosphane is widely employed as a reagent and ligand in organic and inorganic chemistry.
Triphenylphosphane plays a vital role in key synthetic reactions such as the Wittig reaction, where it facilitates the conversion of aldehydes and ketones into alkenes, and the Staudinger reaction, which is used to form amines from azides.

Triphenylphosphane's steric bulk, contributed by the three large phenyl rings, also makes it an excellent ligand for stabilizing reactive metal centers in homogeneous catalysis, notably in hydroformylation and hydrogenation processes.
Triphenylphosphane exhibits good thermal stability but can slowly oxidize in air to form Triphenylphosphane oxide, especially under prolonged exposure to light and oxygen.

Due to its versatile reactivity, Triphenylphosphane is extensively utilized in the pharmaceutical, agrochemical, and polymer industries, contributing to the synthesis of complex molecules, intermediates, and specialty chemicals.
Handling of this chemical requires attention to avoid inhalation and skin contact, and it should be stored in tightly sealed containers under an inert atmosphere or in a dry environment to prevent degradation.

Triphenylphosphane, frequently abbreviated as TPP, is a crystalline solid extensively used in coordination chemistry as a ligand for transition metal complexes and as a catalyst in diverse organic synthesis reactions.
Structurally, Triphenylphosphane comprises a phosphorus center bonded to three aromatic phenyl rings, imparting steric bulk and electronic richness that significantly enhance its reactivity and functional versatility.
Due to the highly nucleophilic nature of its phosphorus atom, Triphenylphosphane is prominently utilized in the preparation of Wittig reagents and serves as a critical agent in notable synthetic methodologies such as the Mitsunobu reaction and Staudinger reactions.

Market Overview of Triphenylphosphane:
The global market for Triphenylphosphane is driven primarily by increasing demand within pharmaceutical, agrochemical, polymer, and specialty chemical sectors, which consistently explore advanced chemical synthesis methods.
The substantial rise in research activities and industrial applications, particularly in Asia-Pacific and European regions, continues to significantly bolster market growth and expansion.

The global Triphenylphosphane market is experiencing steady growth, driven by its critical role as a ligand and reagent in various chemical processes.
In 2022, the market was valued at approximately $150 million, and it's projected to reach $220 million by 2030, growing at a CAGR of 5.0% from 2024 to 2030.​

Uses of Triphenylphosphane:
Triphenylphosphane is a highly versatile chemical with numerous applications across multiple industries, owing to its strong nucleophilic character, reducing properties, and ability to act as a ligand.
One of its principal uses is in organic synthesis, where Triphenylphosphane serves as a reagent for various key reactions.

Triphenylphosphane is extensively employed in the Wittig reaction to synthesize alkenes from carbonyl compounds, a fundamental transformation in the construction of complex organic molecules. 
In addition, Triphenylphosphane is a critical component in the Mitsunobu reaction, facilitating the conversion of alcohols into various functional groups under mild conditions.

In coordination chemistry, Triphenylphosphane acts as a ligand that binds to transition metals, forming stable complexes that are widely utilized in homogeneous catalysis processes, such as hydroformylation, hydrogenation, and cross-coupling reactions.
These catalytic applications are vital for pharmaceutical, petrochemical, and fine chemical industries.

Moreover, Triphenylphosphane functions as a reducing agent in reactions involving the reduction of organic azides to amines (e.g., Staudinger reaction) and the deoxygenation of organic compounds.
In polymer chemistry, Triphenylphosphane serves as a catalyst or additive to improve polymerization processes and the properties of final polymer products.

The chemical is also used in the synthesis of specialty chemicals, dyes, pigments, and agrochemicals where precise control over reaction pathways and high purity of products are essential.
In research laboratories, Triphenylphosphane is frequently used to generate phosphorus ylides and to assist in the study of reaction mechanisms due to its well-understood and predictable behavior in chemical transformations.

Triphenylphosphane finds widespread use as an essential reagent in organic chemical synthesis, an active catalyst in polymerization reactions, and an efficient ligand in coordination chemistry with transition metals.
Triphenylphosphane plays a crucial role in the production processes of pharmaceuticals, agrochemicals, specialty chemicals, and other diverse chemical products.

Organic Synthesis:
Triphenylphosphane is critical in key reactions such as the Wittig reaction, Mitsunobu reaction, Staudinger reaction, and Appel reaction.
Triphenylphosphane facilitates the construction of carbon-carbon bonds and the selective transformation of functional groups.

Catalysis and Ligand Chemistry:
Triphenylphosphane acts as a ligand in many metal-catalyzed reactions, including hydroformylation, hydrogenation, and cross-coupling reactions.
Triphenylphosphane's ability to stabilize metal centers greatly enhances catalytic efficiency.

Industrial Use:
Triphenylphosphane is utilized in the production of pharmaceuticals, agrochemicals, specialty polymers, and materials requiring controlled reactivity or stabilization.
Triphenylphosphane also acts as a scavenger for halogens and oxidants in complex chemical processes.

Triphenylphosphane is used in the following products: perfumes and fragrances, pH regulators and water treatment products and laboratory chemicals.
Triphenylphosphane is used in the following areas: health services and scientific research and development.

Triphenylphosphane is used for the manufacture of: chemicals.
Release to the environment of Triphenylphosphane can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, in processing aids at industrial sites, as processing aid and in the production of articles.

Other Industry Uses:
Intermediates
Dyes
Stabilizing agent
Not Known or Reasonably Ascertainable
Binder
Paint additives and coating additives not described by other categories
Catalyst
Processing aids, not otherwise listed

Consumer Uses:
Triphenylphosphane is used in the following products: biocides (e.g. disinfectants, pest control products) and lubricants and greases.
Other release to the environment of Triphenylphosphane is likely to occur from: indoor use as processing aid, outdoor use as processing aid, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids).

Other Consumer Uses:
Processing aids, not otherwise listed
Catalyst
Dyes

Widespread uses by professional workers:
Triphenylphosphane is used in the following products: perfumes and fragrances, coating products, pH regulators and water treatment products and laboratory chemicals.
Triphenylphosphane is used in the following areas: health services and scientific research and development.
Other release to the environment of Triphenylphosphane is likely to occur from: outdoor use and indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).

Applications of Triphenylphosphane:
Triphenylphosphane finds a broad range of applications across the chemical, pharmaceutical, and materials industries due to its reactivity, stability, and ability to form stable complexes with transition metals.
In organic chemistry, Triphenylphosphane is a key reagent for important transformations, such as the Wittig reaction for alkene synthesis and the Mitsunobu reaction for functional group interconversions.
These applications are crucial in the development of pharmaceuticals, agrochemicals, and specialty chemicals.

In homogeneous catalysis, Triphenylphosphane is widely used as a ligand to stabilize metal complexes, particularly in hydroformylation, hydrogenation, carbonylation, and cross-coupling reactions (e.g., Suzuki, Heck, Stille reactions).
These catalytic processes are fundamental for the industrial production of fine chemicals, polymers, and intermediates.

In polymer chemistry, Triphenylphosphane serves as an additive or catalyst, improving the control of polymerization reactions and enhancing the properties of the resulting materials.
Triphenylphosphane also plays a role in materials science for modifying surfaces and creating functionalized polymers with specialized properties.

Additionally, Triphenylphosphane is used in the synthesis of organophosphorus compounds, preparation of phosphonium salts, deoxygenation of organic compounds, and reduction of azides to amines through the Staudinger reaction.
In laboratory settings, Triphenylphosphane assists in mechanistic studies and the generation of phosphorus ylides, making it an invaluable tool for academic and industrial research.

Triphenylphosphane's utility across diverse fields stems from its combination of strong nucleophilicity, chemical stability, and compatibility with various reaction environments, making it an essential component in modern chemical synthesis and catalysis.

Other Applications:
Pharmaceutical synthesis for drug intermediates
Agrochemical formulations and pesticide synthesis
Polymerization catalysis for specialty polymers
Coordination chemistry in transition metal-catalyzed reactions
Manufacture of synthetic dyes, pigments, and advanced chemical intermediates

Features of Triphenylphosphane:
High nucleophilicity and reducing capability
Exceptional thermal stability and low volatility
Minimal polarity enhancing solubility in nonpolar solvents
Bulky phenyl substituents providing effective steric hindrance

Benefits of Triphenylphosphane:
Facilitates highly selective and efficient synthetic pathways
Significantly improves reaction rates and overall yields
Offers versatility across diverse chemical synthesis and industrial processes
Enhances control over reaction selectivity and outcomes

General Manufacturing Information of Triphenylphosphane:

Industry Processing Sectors:
Transportation Equipment Manufacturing
All Other Basic Organic Chemical Manufacturing
Not Known or Reasonably Ascertainable
Synthetic Rubber Manufacturing
All Other Chemical Product and Preparation Manufacturing
Plastics Product Manufacturing
Synthetic Dye and Pigment Manufacturing

Preparation and Structure of Triphenylphosphane:
Triphenylphosphane can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium.

The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium:
PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl

Triphenylphosphane crystallizes in triclinic and monoclinic modification.
In both cases, the molecule adopts a pyramidal structure with propeller-like arrangement of the three phenyl groups.

Principal reactions with chalcogens, halogens, and acids:

Oxidation:

Triphenylphosphane undergoes slow oxidation by air to give Triphenylphosphane oxide, Ph3PO:
2 PPh3 + O2 → 2 OPPh3

This impurity can be removed by recrystallisation of Triphenylphosphane from either hot ethanol or isopropanol.
This method capitalizes on the fact that OPPh3 is more polar and hence more soluble in polar solvents than Triphenylphosphane.

Triphenylphosphane abstracts sulfur from polysulfide compounds, episulfides, and elemental sulfur.
Simple organosulfur compounds such as thiols and thioethers are unreactive, however.

The phosphorus-containing product is Triphenylphosphane sulfide, Ph3PS.
This reaction can be employed to assay the "labile" S0 content of a sample, say vulcanized rubber.

Triphenylphosphane selenide, Ph3PSe, may be easily prepared via treatment of Triphenylphosphane with red (alpha-monoclinic) Se.
Salts of selenocyanate, SeCN−, are used as the Se0 source. 
Triphenylphosphane can also form an adduct with Te, although this adduct primarily exists as (Ph3P)2Te rather than PPh3Te.

Aryl azides react with Triphenylphosphane to give phosphanimines, analogues of OPPh3, via the Staudinger reaction.

Illustrative is the preparation of Triphenylphosphane phenylimide:
PPh3 + PhN3 → PhNPPh3 + N2

The phosphanimine can be hydrolyzed to the amine.

Typically the intermediate phosphanimine is not isolated.
PPh3 + RN3 + H2O → OPPh3 + N2 + RNH2

Chlorination:
Cl2 adds to PPh3 to give Triphenylphosphane dichloride ([PPh3Cl]Cl), which exists as the moisture-sensitive phosphonium halide.
This reagent is used to convert alcohols to alkyl chlorides in organic synthesis.

Bis(Triphenylphosphane)iminium chloride (PPN+Cl−, formula [(C6H5)3P)2N]Cl is prepared from Triphenylphosphane dichloride:
2 Ph3PCl2 + NH2OH·HCl + Ph3P → {[Ph3P]2N}Cl + 4HCl + Ph3PO

Protonation:
Triphenylphosphane is a weak base (aqueous pKaH = 2.73, determined electrochemically), although it is a considerably stronger base than NPh3 (estimated aqueous pKaH < −3).

Triphenylphosphane forms isolable triphenylphosphonium salts with strong acids such as HBr:
P(C6H5)3 + HBr → [HP(C6H5)3]+Br−

Organic reactions:
Triphenylphosphane is widely used in organic synthesis.
The properties that guide Triphenylphosphane's usage are its nucleophilicity and its reducing character.

The nucleophilicity of Triphenylphosphane is indicated by its reactivity toward electrophilic alkenes, such as Michael-acceptors, and alkyl halides.
Triphenylphosphane is also used in the synthesis of biaryl compounds, such as the Suzuki reaction.

Quaternization:
Triphenylphosphane combines with alkyl halides to give phosphonium salts.

This quaternization reaction is particularly fast for benzylic and allylic halides:
PPh3 + CH3I → [CH3PPh3]+I−

These salts, which can often be isolated as crystalline solids, react with strong bases to form ylides, which are reagents in the Wittig reactions.

Aryl halides will quaternize PPh3 to give tetraphenylphosphonium salts:
PPh3 + PhBr → [PPh4]Br

The reaction however requires elevated temperatures and metal catalysts.

Mitsunobu reaction:
In the Mitsunobu reaction, a mixture of Triphenylphosphane and diisopropyl azodicarboxylate ("DIAD", or its diethyl analogue, DEAD) converts an alcohol and a carboxylic acid to an ester.
DIAD is reduced as it serves as the hydrogen acceptor, and the PPh3 is oxidized to OPPh3.

Appel reaction:
In the Appel reaction, a mixture of PPh3 and CX4 (X = Cl, Br) is used to convert alcohols to alkyl halides.

Triphenylphosphane oxide (OPPh3) is a byproduct.
PPh3 + CBr4 + RCH2OH → OPPh3 + RCH2Br + HCBr3

This reaction commences with nucleophilic attack of PPh3 on CBr4, an extension of the quaternization reaction listed above.

Deoxygenation:

The easy oxygenation of PPh3 is exploited in Triphenylphosphane's use to deoxygenate organic peroxides, which generally occurs with retention of configuration:
PPh3 + RO2H → OPPh3 + ROH (R = alkyl)

Triphenylphosphane is also used for the decomposition of organic ozonides to ketones and aldehydes, although dimethyl sulfide is more popular for the reaction as the side product, dimethyl sulfoxide is more readily separated from the reaction mixture than Triphenylphosphane oxide.
Aromatic N-oxides are reduced to the corresponding amine in high yield at room temperature with irradiation.

Sulfonation:
Sulfonation of PPh3 gives tris(3-sulfophenyl)phosphine, P(C6H4-3-SO3−)3 (TPPTS), usually isolated as the trisodium salt.
In contrast to PPh3, TPPTS is water-soluble, as are its metal derivatives.
Rhodium complexes of TPPTS are used in certain industrial hydroformylation reactions.

Reduction to diphenylphosphide:
Lithium in THF as well as Na or K react with PPh3 to give Ph2PM (M = Li, Na, K).
These salts are versatile precursors to tertiary phosphines.
For example, 1,2-dibromoethane and Ph2PM react to give Ph2PCH2CH2PPh2.

Weak acids such ammonium chloride, convert Ph2PM (M = Li, Na, K) into diphenylphosphine:
(C6H5)2PM + H2O → (C6H5)2PH + MOH

Transition metal complexes:
Triphenylphosphane binds well to most transition metals, especially those in the middle and late transition metals of groups 7–10.
In terms of steric bulk, PPh3 has a Tolman cone angle of 145°, which is intermediate between those of P(C6H11)3 (170°) and P(CH3)3 (115°).

In an early application in homogeneous catalysis, NiBr2(PPh3)2 was used by Walter Reppe for the synthesis of acrylate esters from alkynes, carbon monoxide, and alcohols.
The use of PPh3 was popularized by its use in the hydroformylation catalyst RhH(PPh3)3(CO).

Polymer-anchored PPh3 derivatives:
Polymeric analogues of PPh3 are known whereby polystyrene is modified with PPh2 groups at the para position. 
Such polymers can be employed in many of the applications used for PPh3 with the advantage that the polymer, being insoluble, can be separated from products by simple filtration of reaction slurries.
Such polymers are prepared via treatment of 4-lithiophenyl-substituted polystyrene with chlorodiphenylphosphine (PPh2Cl).

History of Triphenylphosphane:
The history of Triphenylphosphane dates back to the early developments in organophosphorus chemistry in the 19th century.
Triphenylphosphane was first synthesized in the late 19th century during foundational studies on phosphorus compounds, but it gained significant scientific attention in the mid-20th century with the rapid expansion of organic synthesis techniques.

The major breakthrough for Triphenylphosphane came with its central role in the Wittig reaction, discovered by Georg Wittig in the 1950s, a discovery that later earned Wittig the Nobel Prize in Chemistry in 1979.
In this reaction, Triphenylphosphane reacts with alkyl halides to form phosphonium salts, which are then converted into phosphorus ylides, enabling the highly controlled formation of carbon-carbon double bonds — a revolutionary advancement in organic synthesis.

Following its success in the Wittig reaction, Triphenylphosphane became even more prominent in chemical research and industrial processes throughout the second half of the 20th century.
Triphenylphosphane found widespread use as a ligand in coordination chemistry, stabilizing transition metal complexes for homogeneous catalysis, particularly in hydroformylation and hydrogenation processes, critical to large-scale chemical manufacturing.
Triphenylphosphane's versatile reactivity also led to its incorporation into other important reactions such as the Mitsunobu reaction and the Staudinger reaction.

By the 1970s and 1980s, the production and commercial availability of Triphenylphosphane had expanded significantly, allowing for its use not only in academic research but also in large-scale industrial chemical synthesis.
Today, Triphenylphosphane remains a vital and irreplaceable reagent in both laboratory-scale reactions and industrial processes, with continued innovation exploring its use in new catalytic cycles, green chemistry, and materials science.

Handling and Storage of Triphenylphosphane:
Triphenylphosphane should be handled with care in well-ventilated areas, using appropriate personal protective equipment to minimize inhalation, ingestion, and skin or eye contact.
Since Triphenylphosphane is sensitive to air and moisture, it must be stored in tightly sealed containers under an inert atmosphere (such as nitrogen or argon) whenever possible, and kept away from strong oxidizing agents, acids, and halogens.

Storage areas should be cool, dry, and protected from light to prevent gradual oxidation into Triphenylphosphane oxide.
Containers must be clearly labeled and handled according to standard chemical hygiene practices to prevent accidental exposure.

Reactivity and Stability of Triphenylphosphane:
Triphenylphosphane is considered a relatively stable compound under normal storage and handling conditions.
However, Triphenylphosphane can slowly react with atmospheric oxygen, especially in the presence of light, to form Triphenylphosphane oxide.

Triphenylphosphane reacts vigorously with strong oxidizing agents, halogens, and peroxides, leading to the potential release of hazardous decomposition products.
Triphenylphosphane is stable under dry, inert conditions but should be protected from prolonged exposure to air and moisture to preserve its reactivity and purity.

First Aid Measures of Triphenylphosphane:

Inhalation:
If inhaled, immediately move the person to fresh air.
If breathing is difficult, seek medical attention promptly and provide oxygen if available.

Skin Contact:
In case of skin contact, wash thoroughly with soap and water for at least 15 minutes.
Remove contaminated clothing and seek medical attention if irritation develops or persists.

Eye Contact:
Rinse eyes cautiously with water for several minutes.
Remove contact lenses if present and easy to do.
Continue rinsing and consult a physician if irritation continues.

Ingestion:
If swallowed, do not induce vomiting.
Rinse mouth with water and seek immediate medical advice.
Never administer anything by mouth to an unconscious person.

Firefighting Measures of Triphenylphosphane:
Triphenylphosphane is combustible and may emit toxic fumes (such as phosphorus oxides and carbon oxides) when burned.

In case of fire:

Use appropriate fire extinguishing media:
dry chemical powder, carbon dioxide (CO₂), or foam.
Avoid water jets as they may spread the fire.

Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear to protect against toxic fumes and smoke.
Containers exposed to fire should be cooled with water spray, but direct water contact with spilled material should be avoided.

Accidental Release Measures of Triphenylphosphane:
Evacuate non-essential personnel and ventilate the area.
Avoid creating dust.

Carefully sweep up the spilled material using non-sparking tools and transfer Triphenylphosphane into a suitable container for disposal.
Wash the contaminated area with plenty of water while preventing runoff into drains or waterways.
Personnel involved in clean-up should wear appropriate protective clothing, including gloves, goggles, and respirators.

Exposure Controls and Personal Protective Equipment of Triphenylphosphane:

Engineering Controls:
Work in a chemical fume hood or use adequate local exhaust ventilation to minimize airborne exposure.
Ensure eyewash stations and safety showers are accessible in the work area.

Personal Protective Equipment (PPE):

Eye/Face Protection:
Safety goggles or face shield compliant with EN166 standards.

Skin Protection:
Wear chemical-resistant gloves (such as nitrile or neoprene) and lab coats or coveralls.

Respiratory Protection:
If ventilation is inadequate, use an approved respirator with appropriate filters (e.g., for dusts, organic vapors).

General Hygiene Measures:
Avoid eating, drinking, or smoking during handling.
Wash hands thoroughly after handling, and remove contaminated clothing immediately.

Identifiers of Triphenylphosphane:
CAS Number: 603-35-0
ChEBI: CHEBI:183318
ChemSpider: 11283
ECHA InfoCard: 100.009.124
EC Number: 210-036-0
PubChem CID: 11776
RTECS number: SZ3500000
UNII: 26D26OA393
UN number: 3077
CompTox Dashboard (EPA): DTXSID5026251
InChI: InChI=1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
Key: RIOQSEWOXXDEQQ-UHFFFAOYSA-N
InChI=1/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
Key: RIOQSEWOXXDEQQ-UHFFFAOYAH
SMILES: c1ccccc1P(c2ccccc2)c3ccccc3

Linear Formula: (C6H5)3P
CAS Number: 603-35-0
Molecular Weight: 262.29
Beilstein: 610776
EC Number: 210-036-0
MDL number: MFCD00003043
UNSPSC Code: 12352100
PubChem Substance ID: 24900530
NACRES: NA.21

CAS number: 603-35-0
EC number: 210-036-0
Hill Formula: C18H15P
Chemical formula: (C6H5)3P
Molar Mass: 262.29 g/mol
HS Code: 2931 49 90

Properties of Triphenylphosphane:
Chemical formula: C18H15P
Molar mass: 262.292 g·mol−1
Appearance: White Solid
Density: 1.1 g cm−3, solid
Melting point: 80 °C (176 °F; 353 K)
Boiling point: 377 °C (711 °F; 650 K)
Solubility in water: Insoluble
Solubility: organic solvents
Acidity (pKa): 7.64 (pKa of conjugate acid in acetonitrile)
2.73 (pKa of conjugate acid, aqueous scale)
Magnetic susceptibility (χ): -166.8·10−6 cm3/mol
Refractive index (nD): 1.59; εr, etc.

vapor density: 9 (vs air)
Quality Level: 200
vapor pressure: 5 mmHg ( 20 °C)
product line: ReagentPlus®
Assay: 99%
feature: achiral
parameter: air stable
bp: 377 °C (lit.)
mp: 79-81 °C (lit.)
functional group: phosphine
SMILES string: c1ccc(cc1)P(c2ccccc2)c3ccccc3
InChI: 1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
InChI key: RIOQSEWOXXDEQQ-UHFFFAOYSA-N

Boiling point: 377 °C (1013 hPa)
Density: 1.07 g/cm3 (80 °C)
Flash point: 182 °C
Ignition temperature: 425 °C
Melting Point: 80.5 °C
Vapor pressure: 0.0000012 hPa (20 °C)
Bulk density: 500 - 600 kg/m3
Solubility: <0.0001 g/l

Molecular Weight: 262.3 g/mol
XLogP3-AA: 4.6
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 3
Exact Mass: 262.091137476 Da
Monoisotopic Mass: 262.091137476 Da
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 19
Complexity: 202
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Triphenylphosphane:
Assay (GC, area%): ≥ 99.0 % (a/a)
Melting range (lower value): ≥ 79 °C
Melting range (upper value): ≤ 82 °C
Identity (IR): passes test

Structure of Triphenylphosphane:
Molecular shape: Pyramidal
Dipole moment: 1.4 - 1.44 D

Related compounds of Triphenylphosphane:
Triphenylamine
Triphenylarsine
Triphenylstibine
Triphenylphosphane oxide
Triphenylphosphane sulfide
Triphenylphosphane dichloride
Triphenylphosphane selenide
Pd(PPh3)4

Related tertiary phosphines:
Trimethylphosphine
Phosphine

Names of Triphenylphosphine:

Regulatory process names:
Triphenylphosphine
Triphenylphosphine
triphenylphosphine

Preferred IUPAC name:
Triphenylphosphane

IUPAC names:
Phosphine, triphenyl-
Triphenilphosphine
triphenyl phosphine
Triphenylphosphane
triphenylphosphane
Triphenylphosphin
TRIPHENYLPHOSPHINE
Triphenylphosphine
triphenylphosphine
TRIPHENYLPHOSPHINE
Triphenylphosphine
Trisphenylphosphine

Trade names:
Phosphine, triphenyl- (7CI, 8CI, 9CI)
Phosphortriphenyl
TPP
Triphenylphosphan
Triphenylphosphane
Triphenylphosphide
Triphenylphosphin
Triphenylphosphine
Triphenylphosphorus

Other identifiers:
112771-47-8
1198579-87-1
603-35-0
630403-25-7