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4-Biphenylboronic acid
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Name

4-Biphenylboronic acid

 EINECS -0
CAS No. 5122-94-1 Density 1.184 g/cm3
PSA 40.46000 LogP 1.03340
Solubility Insoluble in water. Melting Point 232-245 °C(lit.)
Formula C12H11BO2 Boiling Point 385.504 °C at 760 mmHg
Molecular Weight 198.029 Flash Point 186.946 °C
Transport Information N/A Appearance Solid
Safety 26-37/39-36 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 5122-94-1 (4-Biphenylboronic acid) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

4-Biphenylboronicacid (6CI,7CI,8CI);Boronic acid, [1,1'-biphenyl]-4-yl- (9CI);(1,1'-Biphenyl)-4-boronic acid;4-(Dihydroxyboryl)-1,1'-biphenyl;4-Phenylbenzeneboronic acid;p-Biphenylboronic acid;

Article Data 34

4-Biphenylboronic acid Synthetic route

4-bromophenylboronic acid MIDA ester

98-80-6

phenylboronic acid

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; water In tetrahydrofuran at 90℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; Microwave irradiation;95%
121-43-7

Trimethyl borate

92-66-0

4-bromo-1,1'-biphenyl

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.5h;
Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; for 1h; Further stages.;		86%
With hydrogenchloride; n-butyllithium In tetrahydrofuran soln. of n-BuLi in hexanes added dropwise to soln. of bipyridyl compd. at -78°C, stirred at this temp. for 2.5 h, soln. of borate added over 30 min, allowed to warm to room temp. overnight, 10% aq. HCl added, stirred for 1 h at room temp.; extd. into Et2O, washed with concd. soln. of Na2CO3 then with H2O, evapd., recrystd. from H2O/EtOH (95/5), dried in vac. overnight at 60°C;86%
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane BuLi soln. (hexane) addn. to biphenylbromide soln. (THF), mixt. stirring1 h, mixt. addn. to B-compd. soln. (THF) via canula (N2) at -78° C., stirring 1 h, gradual warming to room temp., aq. HCl addn., stirringat room temp. 15 h, solvent removal; under reduced pressure, Et2O addn., org. layer sepn., drying (MgSO4), soln. concn.. oil triturating with hexane, solid repptn. from MeOH/H2O;40%
Stage #1: 4-bromo-1,1'-biphenyl With diisobutylaluminium hydride; magnesium; lithium chloride In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran; toluene at 0℃; Inert atmosphere;

C18H14B2Br2O6(2-)*2K(1+)

98-80-6

phenylboronic acid

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 50℃; for 5h; Inert atmosphere;86%
5419-55-6

Triisopropyl borate

92-66-0

4-bromo-1,1'-biphenyl

7732-18-5

water

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.5h; Inert atmosphere;
Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;
Stage #3: water With hydrogenchloride In tetrahydrofuran; hexane Inert atmosphere;		85%
92-66-0

4-bromo-1,1'-biphenyl

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 4.5h;
Stage #3: With water In tetrahydrofuran; hexane; ethyl acetate		84%
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.5h;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃;		76%
Stage #1: 4-bromo-1,1'-biphenyl With magnesium In tetrahydrofuran for 4h; Heating;
Stage #2: With Trimethyl borate In tetrahydrofuran at 0 - 20℃;		67%
67-56-1

methanol

55124-35-1

diisopropylamine borane

92-66-0

4-bromo-1,1'-biphenyl

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 4-bromo-1,1'-biphenyl In tetrahydrofuran at 70℃;
Stage #3: methanol Further stages;		78%
5419-55-6

Triisopropyl borate

92-66-0

4-bromo-1,1'-biphenyl

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;
Stage #2: Triisopropyl borate In diethyl ether; hexane at -78 - 20℃;		74%
With n-butyllithium In tetrahydrofuran1.53 g (90%)
1104636-67-0

2-([1,1'-biphenyl]-4-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
With 2,3-dimethyl-2,3-butane diol; water In tetrahydrofuran at 90℃; for 1h; Inert atmosphere;74%
688-74-4

boric acid tributyl ester

92-66-0

4-bromo-1,1'-biphenyl

7732-18-5

water

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran at -85 - -80℃; for 1h; Inert atmosphere;
Stage #2: boric acid tributyl ester In tetrahydrofuran at -85 - -80℃; for 2h; Inert atmosphere;
Stage #3: water With hydrogenchloride In tetrahydrofuran for 0.0833333h; Inert atmosphere;		70%

2-(4-bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

98-80-6

phenylboronic acid

5122-94-1

4-biphenylboronic acid

Conditions
ConditionsYield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; water In tetrahydrofuran at 90℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; chemoselective reaction;63%

4-Biphenylboronic acid Specification

The 4-Biphenylboronic acid, with the CAS registry number 5122-94-1, is also known as Biphenyl-4-ylboronic acid. It belongs to the product categories of Boron Compounds; Blocks; Boronic Acids; Substituted Boronic Acids; Boronic Acid; Organoborons; B (Classes of Boron Compounds); Boronic Acids; Boronic Acid Series; Aryl; Boronic Acids; Boronic Acids and Derivatives. This chemical's molecular formula is C12H11BO2 and molecular weight is 198.03. What's more, its IUPAC name is called (4-Phenylphenyl)boronic acid. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 4-Biphenylboronic acid are: (1)ACD/LogP: 3.151; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.15; (4)ACD/LogD (pH 7.4): 3.13; (5)ACD/BCF (pH 5.5): 146.10; (6)ACD/BCF (pH 7.4): 137.66; (7)ACD/KOC (pH 5.5): 1232.99; (8)ACD/KOC (pH 7.4): 1161.81; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 40.46 Å2; (13)Index of Refraction: 1.61; (14)Molar Refractivity: 57.994 cm3; (15)Molar Volume: 167.192 cm3; (16)Polarizability: 22.991×10-24 cm3; (17)Surface Tension: 49.63 dyne/cm; (18)Density: 1.184 g/cm3; (19)Flash Point: 186.946 °C; (20)Enthalpy of Vaporization: 66.906 kJ/mol; (21)Boiling Point: 385.504 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Uses of 4-Biphenylboronic acid: (1) it is used as intermediates of liquid crystals; (2) it is used to produce other chemicals. For example, it can react with Dimethyl 5-bromoisophthalate to get [1,1';4',1'']Terphenyl-3,5-dicarboxylic acid dimethyl ester. This reaction needs reagents Et3N, P(O-tolyl)3, Pd(OAc)2 and solvent dimethylformamide at temperature of 100 °C. The reaction time is 3.5 hours. The yield is 62 %.

4-Biphenylboronic acid can react with Dimethyl 5-bromoisophthalate to get [1,1';4',1'']Terphenyl-3,5-dicarboxylic acid dimethyl ester.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system. It may cause damage to health by inhalation, in contacting with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: OB(O)c2ccc(c1ccccc1)cc2
(2) InChI: InChI=1S/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15H
(3) InChIKey: XPEIJWZLPWNNOK-UHFFFAOYSA-N

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