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92-92-2

Basic Information
CAS No.: 92-92-2
Name: 4-Biphenylcarboxylic acid
Article Data: 440
Molecular Structure:
Molecular Structure of 92-92-2 (4-Biphenylcarboxylic acid)
Formula: C13H10O2
Molecular Weight: 198.221
Synonyms: 4-Biphenylcarboxylicacid (7CI,8CI);Benzoic acid, p-phenyl- (3CI);[1,1'-Biphenyl]-4-carboxylicacid;4-Carboxy-1,1'-biphenyl;4-Carboxybiphenyl;4-Diphenylcarboxylic acid;4-Phenylbenzoic acid;NSC 23040;p-Biphenylcarboxylic acid;p-Phenylbenzoicacid;4-Biphenylbenzoic acid;p-Phenylbenzoic Acid;
EINECS: 202-203-1
Density: 1.185 g/cm3
Melting Point: 220-225 °C(lit.)
Boiling Point: 372.6 °C at 760 mmHg
Flash Point: 170 °C
Solubility: Soluble in alcohol and ether, insoluble in water
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi, HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 37/39-26-36
PSA: 37.30000
LogP: 3.05180
Synthetic route
619-58-9

4-iodobenzoic acid

98-80-6

phenylboronic acid

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium phosphate monohydrate; 4,4'-di-tBu-2,2'-dipyridylpalladium(II) dichloride In methanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling;100%
With potassium carbonate; palladium dichloride In water at 20 - 90℃; Suzuki coupling; Inert atmosphere;99%
With potassium carbonate In water at 90℃; for 0.25h; Suzuki reaction; Inert atmosphere;99%

C21H16N2O4

A

140-29-4

phenylacetonitrile

B

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 100%
B 94%

C22H18N2O5

A

104-47-2

p-methoxybenzylnitrile

B

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 94%
B 100%
183657-71-8

C22H18N2O5

A

7035-03-2

2-methoxy-benzeneacetonitrile

B

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 100%
B 95%
586-76-5

4-Bromobenzoic acid

98-80-6

phenylboronic acid

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate; Pd-complex on fluorous reversed silica gel In water at 80℃; for 16h; Suzuki reaction;100%
With potassium carbonate; carbapalladacycle complex*periodic mesoporous organosilica for 24h; Suzuki coupling; Heating;100%
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 3.5h; Suzuki-Miyaura coupling reaction;100%
124-38-9

carbon dioxide

3315-91-1

4-biphenylylmagnesium bromide

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 4-biphenylylmagnesium bromide In tetrahydrofuran at 20℃; under 3000.3 Torr; gas-liquid flow reactor assembly;
Stage #2: With polymer-supported sulfonic acid In tetrahydrofuran
100%
99-90-1

para-bromoacetophenone

98-80-6

phenylboronic acid

immobilized 4-bromobenzoic acid

immobilized 4-bromobenzoic acid

A

92-91-1

biphenyl-4-acetaldehyde

B

586-76-5

4-Bromobenzoic acid

C

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: para-bromoacetophenone; phenylboronic acid; immobilized 4-bromobenzoic acid With potassium carbonate In water; N,N-dimethyl-formamide
Stage #2: With potassium hydroxide In ethanol; water
A 100%
B 19%
C 81%
3597-91-9

biphenyl-4-yl methanol

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With silica-supported Jones reagent In dichloromethane for 0.035h;99.5%
With diethylene glycol dimethyl ether at 70℃; for 0.583333h; Sonication;96%
With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide In methanol at 20℃; for 6h; In air;89%
720-75-2

methyl 4-phenylbenzoate

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran at 0 - 20℃; for 3h;99%
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 20h;99%
With water In methanol at 30 - 50℃; Rate constant; Thermodynamic data; Kinetics; ΔH(excit), ΔS(excit), log A;
74-11-3

para-chlorobenzoic acid

98-80-6

phenylboronic acid

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 80℃; for 2h; Suzuki Coupling; Green chemistry;99%
With glucosamine-based dicyclohexylarylphosphine; sodium carbonate; palladium diacetate In ethanol; water; toluene at 80℃; Suzuki-Miyaura cross coupling reaction;97%
With sodium hydroxide; polyaniline-supported palladium In water at 80℃; for 4h; Suzuki coupling;97%
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    Chemical Name 4-Biphenylcarboxylic acid Synonyms Biphenyl-4-carboxylic acid; 4-Phenylbenzoic acid CAS No. 92-92-2 EINECS No. 202-203-1

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    Product Name: 4-Biphenylcarboxylic acid CAS: 92-92-2 MF: C13H10O2 MW: 198.22 EINECS: 202-203-1 Mol File: 92-92-2.mol 4-Biphenylcarboxylic acid Structure 4-Biphenylcarboxylic acid Chemical Properties Melting point 220-225 °

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Reported in EPA TSCA Inventory.

Specification

The IUPAC name of 4-Biphenylcarboxylic acid is 4-phenylbenzoic acid. With the CAS registry number 92-92-2, it is also named as 4-Carboxy-(1,1'-biphenyl); Para phenyl benzoic acid. The product's categories are biphenyl derivatives; organic acids; miscellaneous; absolute configuration determination (Exciton Chirality CD Method); analytical chemistry; enantiomer excess & absolute configuration determination. It is white to light yellow crystal powder which is soluble in alcohol and ether, insoluble in water.  

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.43; (4)ACD/LogD (pH 7.4): 0.87; (5)ACD/BCF (pH 5.5): 19.83; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 124.26; (8)ACD/KOC (pH 7.4): 3.47; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.607; (13)Molar Refractivity: 57.77 cm3; (14)Molar Volume: 167.2 cm3; (15)Polarizability: 22.9×10-24 cm3; (16)Surface Tension: 49.1 dyne/cm; (17)Enthalpy of Vaporization: 65.38 kJ/mol; (18)Vapour Pressure: 3.28E-06 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 198.06808; (21)MonoIsotopic Mass: 198.06808; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 15; (24)Complexity: 211.

Preparation of 4-Biphenylcarboxylic acid: It can be obtained by 1-biphenyl-4-yl-ethanone with the reagent O2, Mn(NO3)2 and Co(NO3)2 and solvent acetic acid at 100 °C. The reaction time is 6 hours.

Uses of 4-Biphenylcarboxylic acid: It is used as polarographic analytical reagent. And it is also used in organic synthesis. For example: It reacts with N-phenylselanyl-phthalimide to get (4-phenylphenyl)(phenylseleno)methanone. This reaction needs reagent tri-n-butylphosphine and solvent tetrahydrofuran at temperature of 25 °C. The reaction time is 4.0 hours. The yield is 58 %.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. And it is also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C(O)c2ccc(c1ccccc1)cc2;
2. InChI: InChI=1/C13H10O2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,(H,14,15).