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Biphenyl’s combination of chemical stability, low volatility, and functional versatility make it an important compound in both industrial and chemical research contexts.
Biphenyl is also called phenyl benzene, it is formed by two connected phenyl compounds, is white or colorless to light yellow crystal plate, industrial products is slightly yellow with special fragrance.
Biphenyl is an organic chemical compound composed of two connected benzene rings, making it a simple aromatic hydrocarbon with the formula C₁₂H₁₀.
CAS Number: 92-52-4
Molecular Formula: C12H10
Molecular Weight: 154.21
EINECS Number: 202-163-5
Synonyms: Biphenyl, 1,1'-Biphenyl, 92-52-4, Phenylbenzene, DIPHENYL, 1,1'-Diphenyl, Phenador-X, Tetrosin LY, Carolid AL, Biphenyl [BSI:ISO], 1,1-Biphenyl, Caswell No. 087, FEMA No. 3129, CCRIS 935, NSC 14916, HSDB 530, UNII-2L9GJK6MGN, MCS 1572, EINECS 202-163-5, CP 390, EPA Pesticide Chemical Code 017002, DTXSID4020161, CHEBI:17097, 1, 1'-Diphenyl, AI3-00036, BIPHENYL [FHFI], BIPHENYL [HSDB], BIPHENYL [ISO], DIPHENYL [MI], NSC-14916, DIPHENYL [MART.], BIPHENYL [USP-RS], DTXCID60161, INS NO.230, FEMA 3129, INS-230, EC 202-163-5, E-230, DIPHENYL (MART.), BIPHENYL (USP-RS), Diphenyl (Biphenyl), Dibenzene, Diphenyl (OSHA), Biphenyl (ACGIH:OSHA), Phenylbenzene, 1,1'Biphenyl, USEPA/OPP Pesticide Code: 017002, 202-163-5, 2-ethyl 3,4-dimethyl 4'-bromobiphenyl-2,3,4-tricarboxylate, 3-methylsulfanyl-biphenyl-4-carboxylic acid, 4'-bromo-3-piperidin-1-yl-biphenyl-4-carbonitrile, inchi=1/c12h10/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1-10, zuouzkkeupvfjk-uhfffaoysa-n, Bibenzene, Xenene, Lemonene, PHPH, DIPHENYL-4-D1, MFCD00003054, 2L9GJK6MGN, 4819-98-1, E230, CHEMBL14092, BNL, CAS-92-52-4, diphenyl, 14C-labeled, meta biphenyl, bi-phenyl, 4-Biphenyl, Biphenyl-UL-14C, 4,4'-biphenyl, 1,1''-biphenyl, Biphenyl, >=99%, Biphenyl-4,4'-d2, WLN: RR, 1,1'-Biphenyl, 9CI, bmse000506, Biphenyl, analytical standard, BIDD:ER0669, GAA12099, NSC14916, Tox21_202108, Tox21_300167, BDBM50168002, Biphenyl 100 microg/mL in Methanol, Biphenyl, ReagentPlus(R), 99.5%, STL264192, Biphenyl 10 microg/mL in Cyclohexane, AKOS000119944, FB32431, NCGC00091836-01, NCGC00091836-02, NCGC00091836-03, NCGC00091836-04, NCGC00254175-01, NCGC00259657-01, Biphenyl, Vetec(TM) reagent grade, 99%, BS-42211, DB-038208, B0224, B0465, Biphenyl, PESTANAL(R), analytical standard, NS00010251, EN300-18009, C06588, G77244, Q410915, Biphenyl, certified reference material, TraceCERT(R), F9995-1632, Biphenyl, United States Pharmacopeia (USP) Reference Standard, 26008-28-6, BIPHENYL, 99%BIPHENYL, 99%BIPHENYL, 99%BIPHENYL, 99%;BIPHENYL (DIPHENYL);BIPHENYL 99%;tetrosinly;Xenene;Diphenyl Mixture;BIPHENYL PESTANAL;BIPHENYL, 1GM, NEAT
Biphenyl appears as a white crystalline solid that is practically insoluble in water but dissolves well in organic solvents such as benzene and alcohols.
Biphenyl has been widely employed as a heat transfer medium and a fungistat, particularly in the preservation of citrus fruits during shipping, where it helps prevent mold growth without significantly affecting the fruit's quality.
Moreover, biphenyl serves as a precursor in the synthesis of more complex organic compounds, including pharmaceuticals, dyes, and polymers, due to its ability to undergo chemical modifications such as substitution reactions on the aromatic rings.
Despite its utility, biphenyl must be handled with care since prolonged exposure or ingestion may pose health risks, including irritation to the skin, eyes, and respiratory tract, and some studies have raised concerns about its toxicity at higher doses.
Because of its stable chemical structure, biphenyl exhibits significant thermal stability and resistance to chemical reactions, which makes it useful in various industrial applications.
Commonly used for organic synthesis precursor, is one of the key components of the organic high temperature heating medium.
Biphenyls derivatives include benzidine, diphenyl ether, eight bromine diphenyl ether, polychlorinated biphenyls, etc.
Biphenyl (also known as diphenyl, phenylbenzene, 1,1′-biphenyl, lemonene or BP) is an organic compound that forms colorless crystals.
Particularly in older literature, compounds containing the functional group consisting of biphenyl less one hydrogen (the site at which it is attached) may use the prefixes xenyl or diphenylyl.
Biphenyl has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula (C6H5)2.
It is notable as a starting material for the production of polychlorinated biphenyls (PCBs), which were once widely used as dielectric fluids and heat transfer agents.
Biphenyl is also an intermediate for the production of a host of other organic compounds such as emulsifiers, optical brighteners, crop protection products, and plastics.
Biphenyl is insoluble in water, but soluble in typical organic solvents.
The biphenyl molecule consists of two connected phenyl rings.
Biphenyl is a neutral molecule and fairly non-reactive due to lack of functional group.
However, biphenyl participates in many of the reactions that are typical for benzene, for example, substitution reactions upon treatment with halogens in the presence of a Lewis acid.
Also, it is required to convert biphenyls into the structural analogs containing the active groups in order for it to be able to use for synthetic intermediate for the production of a host of other organic compounds such as emulsifiers, optical brighteners, crop protection products, plastics and pharmaceuticals.
For this, it is important to consider the o,p-directing and/or mdirecting effect, especially when substitution at a specific position is desired i.e. mono, di-, tri- or tetra- substitutions.
Biphenyl is possible to acetylate the carboxylic part, also various other biphenyl derivative synthesis are possible by carrying out the amination, halogenation, sulphonation, alkylation, hydroxylation, metal complexation etc.
Natural biphenyl exists in coal tar, crude oil and natural gas, the mass fraction is 0.20% to 0.20% in coal tar, current preparation methods of biphenyl include coal tar extraction and chemical synthesis.
The chemical bond in the middle of biphenyls can rotate freely, but if there were bulky groups in the four orthos, restricts rotation and would produce resistance isomer.
This type of compounds (such as BINAP) can be used as a chiral ligands. substituted biphenyl by Suzuki reaction and Ullmann coupling reactions.
Biphenyl is a kind of important organic raw materials, widely used in medicine, pesticides, dyes, liquid crystal materials, etc.
Can be used in the synthesis of plasticizer, preservatives, can also be used to make fuel, engineering plastic and high energy fuel.
Biphenyl is a white or slightly yellow scaly crystal, has a unique fragrance.
Insoluble in water, acid and alkali, soluble in alcohol, ether, benzene and other organic solvents.
Biphenyl is a solid at room temperature, with a melting point of 69.2 °C (156.6 °F).
In the gas phase the molecule exists in two enantiomorphic twisted forms with an angle between the planes of the two rings of 44.4(2)°.
In the room-temperature solid, biphenyl is crystalline with space group P21/c, which does not allow for chiral crystals.
In the first structure determination in the solid state the molecule was described as perfectly planar within the limits of error.
The planar arrangement in the crystalline phase I is assumed to result from dynamic disorder, i.e. it represents an average of two twisted structures.
The lower temperature solid phases II and III have been described as modulated structures with the biphenyl molecules being locked in one of the two non-planar conformations with torsion angles ranging from 9 to 21°.
A study from 2021 concludes that in the crystalline phase at 100 K there is no double-well potential associated with the two twisted conformations, but the potential energy is minimized to zero twist.
Relative to the free molecule it represents therefore a transition state of inversion stabilized by the intermolecular interactions in a molecular crystal.
Biphenyl occurs naturally in coal tar, crude oil, and natural gas and can be isolated from these sources via distillation.
It is produced industrially as a byproduct of the dealkylation of toluene to produce methane: C6H5CH3 + C6H6 → C6H5−C6H5 + CH4
The other principal route is by the oxidative dehydrogenation of benzene: 2 C6H6 + ½ O2 → C6H5−C6H5 + H2O
In the laboratory, biphenyl can also be synthesized by treating phenylmagnesium bromide with copper(II) salts.
Biphenyl can also be prepared using diazonium salts.
When aniline is treated with NaNO2+dilute HCl at 5°C, it yields benzene diazonium chloride.
When this is further reacted with benzene, biphenyl is formed.
This is known as the Gomberg–Bachmann reaction.
Melting point: 68-70 °C (lit.)
Boiling point: 255 °C (lit.)
Density: 0.992
bulk density: 600 kg/m3
vapor density: 5.31 (vs air)
vapor pressure: 9.46 mm Hg (115 °C)
refractive index: 1.475
FEMA: 3129 | BIPHENYL
Flash point: 113 °C
storage temp.: Store below +30°C.
solubility: Soluble in alcohol and ether
form: Crystalline Powder, Crystals or Flakes
color: White to faint yellow
Specific Gravity: 0.992
Odor: pleasant odor
biological source: synthetic
Odor Type: green
explosive limit: 0.6%, 111°F
Water Solubility: insoluble
JECFA Number: 1332
Merck: 14,3314
BRN: 1634058
Henry's Law Constant: 2.92 at 25 °C (air stripping-GC, Destaillats and Charles, 2002)
Exposure limits: NIOSH REL: TWA 0.2 ppm, IDLH 100 mg/m3; OSHA PEL: TWA 0.2 ppm; ACGIH TLV: TWA 0.2 ppm.
Dielectric constant: 20.0 (Ambient)
Stability: Stable. Combustible. Incompatible with strong oxidising agents.
InChIKey: ZUOUZKKEUPVFJK-UHFFFAOYSA-N
LogP: 4.008 at 25℃
Biphenyl is an organic compound with chemical formula of C12H10.
It is a white crystalline powder, insoluble in water, soluble in ether, ethanol, carbon tetrachloride, dioxane, aromatic hydrocarbons, etc.
Biphenyl is mainly used as solvent, heat transfer agent, fruit mildew inhibitor and organic synthesis.
Biphenyl, also called diphenyl, consists of two benzene rings joined by a single bond.
It exists as colorless to yellowish crystals, has a distinctive odor, and occurs naturally in oil, natural gas, and coal tar.
Biphenyl is a clear colorless liquid with a pleasant odor and stable organic compound.
Biphenyl is combustible at high temperatures, producing carbon dioxide and water when combustion is complete.
Partial combustion produces carbon monoxide, smoke, soot, and low molecular weight hydrocarbons.
Biphenyl is used extensively in the production of heat-transfer fl uids, for example, as an intermediate for polychlorinated biphenyls, and dye carriers for textile dyeing.
It is also used as a mold retardant in citrus fruit wrappers, in the formation of plastics, optical brighteners, and hydraulic fluids.
A benzenoid aromatic compound that consists of two benzene rings connected by a single covalent bond.
Biphenyl occurs naturally in coal tar, crude oil, and natural gas. Formerly used as a fungicide for citrus crops.
If Biphenyl gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids.
If Biphenyl contacts theskin, remove contaminated clothing and wash immediatelywith soap and water.
Biphenyl has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped.
When this chemical has been swallowed, get medical attention.
Rotation about the single bond in biphenyl, and especially its ortho-substituted derivatives, is sterically hindered.
For this reason, some substituted biphenyls show atropisomerism; that is, the individual C2-symmetric-isomers are optically stable.
Some derivatives, as well as related molecules such as BINAP, find application as ligands in asymmetric synthesis.
In the case of unsubstituted biphenyl, the equilibrium torsional angle is 44.4° and the torsional barriers are quite small, 6.0 kJ/mol at 0° and 6.5 kJ/mol at 90°.
Adding ortho substituents greatly increases the barrier: in the case of the 2,2'-dimethyl derivative, the barrier is 17.4 kcal/mol (72.8 kJ/mol).
Substituted biphenyls have many uses.
They are prepared by various coupling reactions including the Suzuki-Miyaura reaction and the Ullmann reaction.
Polychlorinated biphenyls were once used as cooling and insulating fluids and polybrominated biphenyls are flame retardants.
The biphenyl motif also appears in drugs such as diflunisal and telmisartan.
The abbreviation E7 stands for a liquid crystal mixture consisting of several cyanobiphenyls with long aliphatic tails used commercially in liquid crystal displays (5CB, 7CB, 8OCB and 5CT).
A variety of benzidine derivatives are used in dyes and polymers.
Research into biphenyl liquid crystal candidates mainly focuses on molecules with highly polar heads (for example cyano or halide groups) and aliphatic tails.
Biphenyl is part of the active group in the antibiotic oritavancin.
Biphenyl is not only valued for its chemical stability but also for its role as an intermediate in organic synthesis, where it can be transformed into various substituted biphenyl derivatives that serve as ligands in catalysis or as building blocks in the manufacture of liquid crystals used in display technologies.
Additionally, biphenyl’s aromatic rings contribute to its ability to participate in pi-pi stacking interactions, which are important in the design of molecular materials and supramolecular chemistry.
In industrial settings, biphenyl is sometimes used as a solvent or plasticizer, where its non-polar nature facilitates the dissolution or softening of certain polymers, enhancing their processing characteristics.
From a safety perspective, biphenyl is considered moderately toxic; inhalation of its dust or vapors can lead to respiratory irritation and central nervous system effects, while chronic exposure may cause liver or kidney damage in animal studies, highlighting the need for adequate ventilation and protective equipment during handling.
Environmentally, biphenyl can persist due to its resistance to biodegradation, leading to concerns about accumulation in soil and water systems, where it may impact aquatic organisms.
Regulatory bodies have established exposure limits and guidelines for its use to mitigate such risks, and ongoing research continues to evaluate its long-term effects on human health and ecosystems.
Uses:
Biphenyl is used in organic syntheses, heat transfer fluids, dye carriers, food preservatives, as an intermediate for polychlorinated biphenyls, and as a fungistat in the packaging of citrus fruits.
Biphenyl with high thermal stability and low vapor pressure, long often alone or with diphenyl ether and blend to used as heating medium. Component of biphenyl and terphenyl (including Biphenyl 13%, terphenyl 61%) can effectively absorb radiation, can be used as a heating medium for nuclear power plant.
And three terphenyl([91-94-4]) is the byproduct of benzene pyrolysis to produce Biphenyl, according to the different reaction conditions, the proportion of the reaction product of biphenyl and terphenyl within a certain range of change, in general, Biphenyl: terphenyl=78:1. Biphenyl is used as a carrier, and its derivatives of ethyl biphenyl, diethyl biphenyl and triethyl biphenyl senior can be used as solvents, used in pressure sensitive dye solvent of carbon paper.
Biphenyl is used to prevent fungal attack on stored citrus fruit. It is impregnated into fruit wraps.
As heat transfer agent; fungistat for oranges (applied to inside of shipping container or wrappers); in organic syntheses.
Biphenyl is used as an antifungal agent to preserve citrus fruit, in citrus wrappers to retard mold growth, in heat transfer fluids, in dye carriers for textiles and copying paper, as a solvent in pharmaceutical production, in optical brighteners, and as an intermediate for the production of a wide range of organic compounds.
Biphenyl is an important organic raw material, which is widely used in medicine, pesticide, dye, liquid crystal materials and other fields.
Biphenyl can be used to synthesize plasticizers and preservatives, and can also be used to manufacture fuels, engineering plastics and high-energy fuels.
Biphenyls are found in coal tar, crude oil and natural gas.
The preparation methods of biphenyl include chemical synthesis of biphenyl by pyrolysis of benzene and separation and extraction of biphenyl from various coal tar oil fractions.
The mass fraction of biphenyl in coal tar is 0.20% - 0.40%. Coal tar extraction and chemical synthesis coexist.
Biphenyl is combustible. In case of high temperature, open fire and oxidant, it is dangerous to burn.
It should be stored in a cool and ventilated warehouse away from kindling and heat source.
Biphenyl should be stored separately from oxidants and strong acids.
It should be loaded and unloaded gently to keep the package intact.
Biphenyl is used as heat exchanger and impregnator of fruit packaging paper.
Biphenyl can be used in organic synthesis. Biphenyl is the raw material of engineering plastics polysulfone.
It is used to prepare Trichlorobenzene and pentachlorophenyl.
Biphenyl is used as heat carrier, preservative, dye and so on.
Biphenyl is used as a reference material for chromatographic analysis.
Biphenyl is the intermediate of rodenticides rodenticide modek and bromadine, and it is an organic carrier with good performance.
Lacking functional groups, biphenyl is fairly non-reactive, which is the basis of its main application: in a eutectic mixture with diphenyl ether, as a heat transfer agent.
Biphenyl does undergo sulfonation which, followed by base hydrolysis, produces p-hydroxybiphenyl and p,p′-dihydroxybiphenyl, which are useful fungicides.
In other substitution reactions, it undergoes halogenation.
Polychlorinated biphenyls were once popular pesticides.
Biphenyl is widely used in various industrial and chemical applications due to its unique chemical and physical properties.
One of its primary uses is as a heat transfer fluid, especially in high-temperature systems, because of its excellent thermal stability and ability to maintain liquid form over a broad temperature range.
Additionally, biphenyl serves as a fungistat and preservative, particularly in the citrus fruit industry, where it is applied to prevent mold growth and extend the shelf life of fruits during storage and transportation without compromising their freshness or taste.
In the field of organic synthesis, biphenyl acts as a key intermediate or starting material for the production of a wide range of chemicals, including dyes, pharmaceuticals, and agrochemicals, where its biphenyl core can be functionalized to create more complex molecules with specific desired properties.
Moreover, biphenyl derivatives are essential components in the manufacture of liquid crystals, which are critical for the display technology used in devices like computer monitors, televisions, and smartphones.
Biphenyl is also utilized as a solvent and plasticizer in polymer processing, where it helps to modify the viscosity and mechanical properties of plastics, enabling improved molding and extrusion processes.
Beyond industrial applications, biphenyl’s chemical structure makes it valuable in research laboratories for studying aromatic chemistry and designing new materials with specialized functions.
Despite its usefulness, all applications of biphenyl must consider its toxicity and environmental persistence, ensuring that it is handled responsibly to prevent adverse effects.
In addition to the uses already mentioned, biphenyl finds application as a precursor in the synthesis of heat-resistant polymers and high-performance materials, where the rigid biphenyl structure imparts enhanced mechanical strength and thermal stability to the final products.
This makes biphenyl-based polymers highly desirable for aerospace, automotive, and electronic industries, where materials are often subjected to extreme temperatures and mechanical stress.
Furthermore, biphenyl derivatives are employed as ligands in homogeneous catalysis, facilitating various chemical reactions with high selectivity and efficiency, which is particularly valuable in pharmaceutical manufacturing to produce complex molecules with minimal by-products.
In environmental science, biphenyl compounds serve as model substances for studying the behavior and degradation of persistent organic pollutants, aiding in the development of bioremediation strategies and pollution control technologies.
Additionally, biphenyl is used in specialized lubricants and hydraulic fluids, where its stability helps maintain performance under demanding operating conditions.
In some niche applications, biphenyl acts as a component in organic light-emitting diodes (OLEDs) and photovoltaic cells, contributing to advances in renewable energy and display technologies.
Health Hazard:
Biphenyl cause acute effects with symptoms that include, but are not limited to, polyuria, accelerated breathing, lacrimation, anorexia, weight loss, muscular weakness, coma, fatty liver cell degeneration, and severe nephrotic lesions.
Exposure to biphenyl fumes for short periods of time causes nausea, vomiting, irritation of the eyes and respiratory tract, and bronchitis.
Breathing small amounts of 1,1’-biphenyl over long periods of time causes damage to the liver and the nervous system of exposed workers.
Breathing the mists, vapors, or fumes may irritate the nose, throat, and lungs.
Depending on the concentration and duration of exposure, the symptoms include, but are not limited to, sore throat, coughing, labored breathing, sneezing, a burning sensation, and the effects of CNS depression.
Symptoms may include headache, excitation, euphoria, dizziness, incoordination, drowsiness, light-headedness, blurred vision, fatigue, tremors, convulsions, loss of consciousness, coma, respiratory arrest, and death, depending on the concentration and duration of exposure
Safety Profile:
Biphenyl poses several health and environmental hazards that require careful management to prevent harm.
From a human health perspective, exposure to biphenyl can occur through inhalation, ingestion, or skin contact, and it may cause irritation to the eyes, skin, and respiratory tract.
Prolonged or repeated exposure has been linked to more serious effects such as central nervous system depression, manifested by symptoms like dizziness, headaches, and nausea.
Animal studies have also indicated that biphenyl can cause liver and kidney damage after chronic exposure, suggesting potential systemic toxicity.
Poison by intravenous route.
Moderately toxic by ingestion. A powerful irritant byinhalation in humans.
Human systemic effects byinhalation of very small amounts: flaccid paralysis, nauseaor vomiting, and other unspecified gastrointestinal effects.Que
Biphenyls are low toxic and irritating to humans.
Its steam can stimulate eyes, nose and trachea, cause loss of appetite and vomiting, and has certain toxicity to the nervous system, digestive system and kidney.
Biphenyl has stimulating effect and damages myocardium, liver and kidney.
It exists in flue-cured tobacco, oriental tobacco and flue gas.
Biphenyl prevents the growth of molds and fungus, and is therefore used as a preservative (E230, in combination with E231, E232 and E233), particularly in the preservation of citrus fruits during transportation.
Biphenyl is no longer approved as a food additive in the European Union.
Biphenyl is mildly toxic, but can be degraded biologically by conversion into nontoxic compounds.
Some bacteria are able to hydroxylate biphenyl and its polychlorinated biphenyls (PCBs).
