BENZOYL CHLORIDE

CAS No.: 98-88-4
EC No.: 202-710-8

Synonyms:
BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE; 98-88-4; Benzoylchloride; Benzenecarbonyl chloride; Benzoic acid, chloride; alpha-Chlorobenzaldehyde; benzoic acid chloride; benzoylchlorid; Benzaldehyde, alpha-chloro-; CCRIS 802; UNII-VTY8706W36; HSDB 383; EINECS 202-710-8; UN1736; BRN 0471389; Benzaldehyde, .alpha.-chloro-; CHEBI:82275; VTY8706W36; Benzoyl chloride, 99%, pure; Benzoyl chloride, 98+%, ACS reagent; Benzoyl chloride, ReagentPlus(R), >=99%; benzoyl chlorid; benzoyl choride; bezoyl chloride; benzoic chloride; BzCl; benzoyl chloride-; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; PhCOCl; Bz-Cl; MFCD00000653; PubChem22045; Benzoyl chloride [UN1736] [Corrosive]; .alpha.-Chlorobenzaldehyde; Benzaldehyde, |A-chloro-; DSSTox_CID_6631; ACMC-20aj01; EC 202-710-8; SCHEMBL1241; BENZOIC ACID,CHLORIDE; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; DSSTox_RID_78168; DSSTox_GSID_26631; 4-09-00-00721 (Beilstein Handbook Reference); KSC486Q7P; Benzoyl Chloride, ACS reagent; CHEMBL2260719; DTXSID9026631; CTK3I6877; KS-00000UUU; Benzoyl chloride, AR, >=99%; Benzoyl chloride, LR, >=99%; OTAVA-BB 1051706; LABOTEST-BB LTBB000456; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; CS-B1785; ZINC2041164; Tox21_200431; ANW-75551; SBB059783; STL264120; Benzoyl chloride, ACS reagent, 99%; AKOS000121308; AS00010; MCULE-3627399529; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; UN 1736; CAS-98-88-4; Benzoyl chloride, purum, >=99% (GC); Benzoyl chloride, ReagentPlus(R), 99%; NCGC00248610-01; NCGC00257985-01; Benzoyl chloride [UN1736] [Corrosive]; Benzoyl chloride, p.a., 98-100.5%; LS-42590; PS-10801; SC-76545; DB-002645; DB-051009; B0105; Benzoyl chloride, 99%, pure, AcroSeal(R); FT-0622741; FT-0639824; ST51046056; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; Benzoyl chloride, SAJ first grade, >=98.0%; C19168; 11273-EP2270015A1; 11273-EP2270114A1; 11273-EP2272841A1; 11273-EP2272972A1; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; 11273-EP2272973A1; 11273-EP2275407A1; 11273-EP2275412A1; 11273-EP2277848A1; 11273-EP2277872A1; 11273-EP2277878A1; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; 11273-EP2277880A1; 11273-EP2279750A1; 11273-EP2281813A1; 11273-EP2281815A1; 11273-EP2284157A1; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; 11273-EP2286811A1; 11273-EP2287159A1; Q412825; F2190-0038; 247-558-3 [EINECS]; 471389; 98-88-4 [RN]; a-Chlorobenzaldehyde; Benzaldehyde, α-chloro-; benzoic acid chloride; Benzoic acid, chloride; Benzoyl chloride [ACD/Index Name] [ACD/IUPAC Name] [Wiki]; Benzoyl chloride [UN1736] [Corrosive]; Benzoylchlorid [German] [ACD/IUPAC Name]; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; Chlorure de benzoyle [French] [ACD/IUPAC Name]; DM6600000; VTY8706W36; 100-09-4 [RN]; 2719-27-9 [RN]; 4-09-00-00721 (Beilstein Handbook Reference) [Beilstein]; 43019-90-5 [RN]; 52947-05-4 [RN]; 59748-37-7 [RN]; ANISIC ACID; Benzaldehyde, α-chloro-; Benzenecarbonyl chloride; BENZOYL CHLORIDE-(RING-13C6); Benzoyl Chloride, ACS reagent; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE|BENZOYL CHLORIDE; benzoylchloride; Benzoyl-d5 Chloride; Cyclohexanecarbonyl chloride [ACD/Index Name] [ACD/IUPAC Name]; EINECS 202-710-8; Hexahydrobenzoyl chloride; InChI=1/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5; MFCD01865658 [MDL number]; O-CHLOROFORMYLBENZENE; PS-10801; UNII:VTY8706W36; UNII-VTY8706W36; α-Chlorobenzaldehyde; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; α-Chlorobenzaldehyde; 苯甲酰氯 [Chinese]; benzenecarbonyl chloride; benzoic acid;  chloride; benzoylchloride; alpha-chlorobenzaldehyde; benzoic acid chloride; benzoylchlorid; benzaldehyde; alpha-chloro; a-chlorobenzaldehyde; ccris 802; unii-vty8706w36; BzCl; Basic Red 1; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOXALONE; Benzoylchlorid; BENZOYL CHLORIDE; BenzoylChlorideGr; chloruredebenzoyle;-Chlorobenzaldehyde; Benzoyl Chloride >BENZOYL CHLORIDE, ACS; alpha-Chlorobenzaldehyde; Benzenecarbonyl chloride; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOIC ACID CHLORIDE; BENZOYL CHLORIDE; LABOTEST-BB LTBB000456; alpha-chloro-benzaldehyd; Benzaldehyde, alpha-chloro-; -Chlorobenzaldehyde; chloruredebenzoyle; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE, REAGENTPLUS, >=99%; BENZOYL CHLORIDE REAGENTPLUSTM >=99%; BENZOYL CHLORIDE, REAGENTPLUS, 99%; BENZOYL CHLORIDE, 99%, A.C.S. REAGENT; BENZOYL CHLORIDE REAGENTPLUS(TM) 99%; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; BENZOYL CHLORIDE, ACS; BenzoylChlorideGr; Benzoyl chloride, 99+%; BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR; Benzoyl chloride, for analysis ACS, 98+%; Benzoyl chloride, pure, 99%; BENZOYL CHLORIDE REAGENT (ACS); BENZOYL CHLORIDE; benzoyl chloride; benzoil klorür; BENZOİL KLORÜR

BENZOYL CHLORIDE

Benzoyl chloride
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Not to be confused with benzyl chloride.
Benzoyl chloride
Benzoyl Chloride
Benzoyl-chloride-3D-balls.png
Benzoyl-chloride-3D-vdW.png
Names
Preferred IUPAC name
Benzoyl chloride
Identifiers
CAS Number    
98-88-4 check
3D model (JSmol)    
Interactive image
Interactive image
ChEBI    
CHEBI:82275
ChEMBL    
ChEMBL2260719
ChemSpider    
7134 check
ECHA InfoCard    100.002.464 Edit this at Wikidata
EC Number    
202-710-8
KEGG    
C19168 check
PubChem CID    
7412
RTECS number    
DM6600000
UNII    
VTY8706W36
UN number    1736
CompTox Dashboard (EPA)    
DTXSID9026631 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula    C7H5ClO
Molar mass    140.57 g·mol−1
Appearance    colorless liquid
Odor    Benzaldehyde like but more pungent
Density    1.21 g/mL, liquid
Melting point    −1 °C (30 °F; 272 K)
Boiling point    197.2 °C (387.0 °F; 470.3 K)
Solubility in water    reacts
Magnetic susceptibility (χ)    -75.8·10−6 cm3/mol
Hazards
Safety data sheet    Fisher Scientific MSDS
GHS pictograms    GHS05: CorrosiveGHS07: Harmful
GHS Signal word    Danger
GHS hazard statements    H302, H312, H314, H317, H332
GHS precautionary statements    P260, P261, P264, P270, P271, P272, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P310, P312, P321, P322, P330, P333+313, P363, P405, P501
NFPA 704 (fire diamond)    
NFPA 704 four-colored diamond
230W
Flash point    72 °C (162 °F; 345 K)
Related compounds
Related compounds    benzoic acid, benzoic anhydride, benzaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

Contents
1    Preparation
2    Reactions
3    References
4    External links
Preparation
Benzoyl chloride is produced from benzotrichloride using either water or benzoic acid:[1]

C6H5CCl3 + H2O → C6H5COCl + 2 HCl
C6H5CCl3 + C6H5CO2H → 2 C6H5COCl + HCl
As with other acyl chlorides, it can be generated from the parent acid and other chlorinating agents phosphorus pentachloride, thionyl chloride, or oxalyl chloride. It was first prepared by treatment of benzaldehyde with chlorine.[2]

An early method for production of benzoyl chloride involved chlorination of benzyl alcohol.[3]

Reactions
It reacts with water to produce hydrochloric acid and benzoic acid:

C6H5COCl + H2O → C6H5CO2H + HCl
Benzoyl chloride is a typical acyl chloride. It reacts with alcohols to give the corresponding esters. Similarly, it reacts with amines to give the amide.[4][5]

It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.[6] With carbanions, it serves again as a source of "PhCO+".[7]

Benzoyl peroxide, a common reagent in polymer chemistry, is produced industrially by treating benzoyl chloride with hydrogen peroxide and sodium hydroxide:[8]

Benzoyl chloride is used in benzoylation treatment to decrease the hydrophobicity of the fiber and to improve fiber–matrix adhesion leading to an increase in the strength of the composite. In benzoylation treatment, the alkali pretreatment is used to activate the hydroxyl groups of the fiber and then the fiber is soaked in benzoyl chloride solution for 15 minutes. Benzoyl chloride which is adhered to the fiber surface is removed by ethanol solution followed by washing with water and drying in an oven. Benzoyl chloride treatment on alkali pretreated sisal fiber exhibits higher thermal stability compared to untreated fiber composites (Joseph et al., 1996).

In this process, the pretreated coir fibers are suspended in 10% NaOH solution and agitated with benzoyl chloride. The mixture is left for 15 min, filtered, washed thoroughly with water and then dried between filter papers. The isolated fibers are then soaked in ethanol for one hour to remove the benzoyl chloride and finally washed with water and dried in the oven at 800°C for 24 h (Chandra Rao et al., 2012).

Acid Chlorides
Linear sweep voltammetry of benzoyl chloride in acetonitrile containing tetra-ethylammonium fluoroborate shows Ep = −1.4 V vs. sce and for heptanoyl chloride Ep = −2.2 V vs. sce [169] The one-electron reduction of acid chlorides at these potentials is a source of carbonyl radicals. Reduction of benzoyl chloride at the peak

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potential gives the stilbene derivative 37. In this reaction, benzil is generated by the union of two benzoyl radicals, then further reduction followed by reaction with benzoyl chloride yields the final product [169]. 

Hydrolysis of benzoyl chloride was followed by measuring the decrease in solution pH values as HCl and benzoic acid were formed. Benzotrichloride was included in these experiments as a control. Since hydrolysis of benzoyl chloride is expected to be very rapid in the initial stages (0.1 min) and thus not observable by HPLC since a minimum sample preparation and HPLC injection time of 20 sec was needed, estimation based on pH measurements was chosen as method.

The authors tested the hydrolysis of benzoyl chloride by measuring the decrease in pH solution at ~25°C as HCl and benzoic acid are formed. Under these conditions the half-life value was <0.25 min at 25°C. Using the formula t1/2 = ln 2 / (kH20), the hydrolysis rate constants calculated was > 2.77 min-1.
GLP standards are not specified. The study sufficiently describes the materials and methodology used, thus the study can be considered Klimisch 2e as it is well documented, meets generally accepted scientific principles and is acceptable for assessment.
Executive summary:
The authors tested the hydrolysis of benzoyl chloride (CAS n° 98-88-4) by measuring the decrease in pH solution at ~25°C as HCl and benzoic acid are formed. Initial concentration of the test substance was 100 ppm and hydrolysis reaction was monitored till no change in pH was evident. The half-life value was estimated using benzotrichloride which was included in this experiment as a control and aid to interpret the pH plots. Under these conditions the half-life value was 0.25 min at 25°C. Using the formula t1/2 = ln 2 / (kH20), the hydrolysis rate constants calculated was >2.77 min-1.

GLP standards are not specified. As the study sufficiently describes the materials and methodology used, the study can be considered reliable with restrictions as it is well documented, meets generally accepted scientific principles and is acceptable for assessment (Klimisch 2e).

Benzoyl chloride price More Price(19)
Manufacturer    Product number    Product description    CAS number    Packaging    Price    Updated    Buy
Sigma-Aldrich    259950    Benzoyl chloride ACS reagent, 99%    98-88-4    5ml    $33.9    2020-08-18    Buy
Sigma-Aldrich    259950    Benzoyl chloride ACS reagent, 99%    98-88-4    1l    $85.6    2020-08-18    Buy
TCI Chemical    B0105    Benzoyl Chloride >98.0%(GC)(T)    98-88-4    25mL    $17    2020-06-24    Buy
TCI Chemical    B0105    Benzoyl Chloride >98.0%(GC)(T)    98-88-4    500mL    $22    2020-06-24    Buy
Alfa Aesar    A14107    Benzoyl chloride, 99+%    98-88-4    250g    $21    2020-06-24    Buy
Benzoyl chloride Chemical Properties,Uses,Production
Physical and Chemical Properties
Its pure product is a colorless and transparent flammable liquid, which is smoking exposed to air in the air. In Industry, it is slightly pale yellow, with a strong pungent odor. Its steam has a strong stimulating effect for eye mucous membranes, skin and respiratory tract, by stimulating the mucous membranes and eyes tear. Benzoyl chloride Melting point is-1.0 ℃, boiling point is 197.2 ℃, and the relative density is 1.212 (20 ℃), while a flash point is 72 ℃, and refractive index (n20) is 1.554. It is soluble in the ether, chloroform, benzene and carbon disulfide. It can gradually decomposed in water or ethanol, ammonia, which generates benzoic acid, generating benzamide, ethyl benzoate and hydrogen chloride. In the laboratory, it can be obtained by distillation of benzoic acid and phosphorus pentachloride under anhydrous conditions. Industrial production process can be obtained by the use of thionyl chloride benzaldehyde. Benzoyl chloride is an important intermediate for preparing dyes, perfumes, organic peroxides, resins and drugs. It is also used in photography and artificial tannin production, which was formerly used as an irritant gas in chemical warfare.
Application
Used for dye intermediates, initiator, UV absorbers, rubber additives, medicine etc.
Benzoyl chloride is intermediate of herbicide metamitron, and insecticide propargite, benzene hydrazine or intermediate food.
Benzoyl chloride is used for organic synthesis, dye and pharmaceutical raw material, manufacturing initiator benzoyl peroxide, t-butyl peroxybenzoate, pesticides and herbicides. In pesticides, it is a new insecticide, which is inducible isoxazole parathion (Isoxathion, Karphos) intermediate. Benzoyl chloride is an important benzoyl and benzyl reagent. Most of benzoyl chloride is used in the production of benzoyl peroxide, and secondly for the production of benzophenone, benzyl benzoate, benzyl cellulose. Benzoyl peroxide catalyzes polymerization initiator for the monomer plastic, polyester, epoxy, acrylic resin production, self-curing agent, which is a glass fiber material, fluorine rubber, silicone crosslinking agents, oil refined, bleached flour, fiber decolorizing Wait. Domestic original benzoyl chloride manufacturing enterprises are more than 20. Some of the manufacturers also produce acid chloride, and the production capacity is 10,000t. However, according to the 2003 survey, the profit is too low, because of the use of small polluting production line, while the use of polluting route is controlled by the government restrictions, and a further raw material price increases. Therefore most of the manufacturers stop the production. Further reaction with the acid chloride can also produce acid anhydride,  and benzoic acid anhydride is the main purpose for acylation agents, which can also be used as a bleaching agent and flux of a component, as well as it can also be used for the preparation of benzoyl peroxide over.
Reagents for the analysis, but also for spices, organic synthesis.
Chemical Properties
Transparent, colorless liquid; pungent odor; vapor causes tears. Soluble in ether and carbon disulfide; decomposes in water. Combustible.
Chemical Properties
Benzoyl chloride is a colorless to slight brown liquid with a strong, penetrating odor.
Uses
Benzoyl Chloride is used in the manufacturing of dye intermediates.
Uses
For acylation, i.e., introduction of the benzoyl group into alcohols, phenols, and amines (Schotten-Baumann reaction); in the manufacture of benzoyl peroxide and of dye intermediates. In organic analysis for making benzoyl derivatives for identification purposes.
Definition
A liquid acyl chloride used as a benzoylating agent.
Production Methods
Benzoyl chloride can be prepared from benzoic acid by reaction with PCl5 or SOCl2, from benzaldehyde by treatment with POCl3 or SO2 Cl2, from benzotrichloride by partial hydrolysis in the presence of H2SO4 or FeCl3, from benzal chloride by treatment with oxygen in a radical source, and from several other miscellaneous reactions. Benzoyl chloride can be reduced to benzaldehyde, oxidized to benzoyl peroxide, chlorinated to chlorobenzoyl chloride and sulfonated to m-sulfobenzoic acid. It will undergo various reactions with organic reagents. For example, it will add across an unsaturated (alkene or alkyne) bond in the presence of a catalyst to give the phenylchloroketone:图
Synthesis Reference(s)
Journal of the American Chemical Society, 73, p. 702, 1951 DOI: 10.1021/ja01146a061
Synthesis, p. 306, 1983
Tetrahedron Letters, 11, p. 4683, 1970
General Description
A colorless fuming liquid with a pungent odor. Flash point 162°F. Lachrymator, irritating to skin and eyes. Corrosive to metals and tissue. Density 10.2 lb / gal. Used in medicine and in the manufacture of other chemicals.
Reactivity Profile
Benzoyl chloride reacts violently with protic solvents such as alcohols, with amines and amides (for example dimethylformamide [Bretherick 1979 p. 6] ) and with inorganic bases. Causes the violent decomposition of dimethyl sulfoxide [Chem. Eng. News 35(9): 87 1957]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Friedel-Crafts acylation of naphthalene using Benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent [Clar, E. et al., Tetrahedron, 1974, 30, 3296].
Hazard
Highly toxic. Strong irritant to skin, eyes, and mucous membranes, and via ingestion, inhala- tion. Upper respiratory tract irritant. Probable car- cinogen.
Health Hazard
INHALATION: may irritate eyes, nose and throat. INGESTION: causes acute discomfort. SKIN: causes irritation and burning.
Chemical Reactivity
Reactivity with Water Slow reaction with water to produce hydrochloric acid fumes. The reaction is more rapid with steam; Reactivity with Common Materials: Slow corrosion of metals but no immediate danger; Stability During Transport: Not pertinent; Neutralizing Agents for Acids and Caustics: Soda ash and water, lime; Polymerization: Does not occur; Inhibitor of Polymerization: Not pertinent.
Safety Profile
Confirmed carcinogen withexperimental tumorigenic data by skin contact. Humansystemic effects by inhalation: unspecified effects onolfaction and respiratory systems. Corrosive effects on theskin, eyes, and mucous membranes by inhalation.Flammable whe
Potential Exposure
Benzoyl chloride is used as a chemical intermediate; in organic synthesis; to produce other chemicals, dyes, perfumes, herbicides, and medicines.
Shipping
UN 1736 Benzoylchloride, Hazard class: 8; Labels: 8—Corrosive material.
Purification Methods
A solution of benzoyl chloride (300mL) in *C6H6 (200mL) is washed with two 100mL portions of cold 5% NaHCO3 solution, separated, dried with CaCl2 and distilled [Oakwood & Weisgerber Org Synth III 113 1955]. Repeated fractional distillation at 4mm Hg through a glass helices-packed column (avoiding porous porcelain or silicon-carbide boiling chips, and hydrocarbon or silicon greases on the ground joints) gave benzoyl chloride that did not darken on addition of AlCl3. Further purification is achieved by adding 3 mole% each of AlCl3 and toluene, standing overnight, and distilling off the benzoyl chloride at 1-2mm [Brown & Jenzen J Am Chem Soc 80 2291 1958]. Refluxing for 2hours with an equal weight of thionyl chloride before distillation has also been used. [Beilstein 9 IV 721.] Strong IRRITANT. Use in a fume cupboard.
Incompatibilities
May form explosive mixture with air. Contact with heat, hot surfaces, and flames causes decomposition, forming phosgene and hydrogen chloride. Water contact may be violent; forms hydrochloric acid. Reactions with amines, alcohols, alkali metals, dimethyl sulfoxide, strong oxidizers, and metal salts may be violent, causing fire and explosions. Attacks metals in the presence of moisture, forming explosive hydrogen gas. Attacks some plastics, rubber or coatings.
Waste Disposal
Pour into sodium bicarbonate solution and flush to sewer.
Benzoyl chloride Preparation Products And Raw materials