4-Biphenylboronic acid supplier

Name
4-Biphenylboronic acid
EINECS -0
CAS No. 5122-94-1
Article Data34
CAS DataBase
Density 1.184 g/cm³
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
Appearance Solid
Safety 26-37/39-36
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
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;
PSA 40.46000
LogP 1.03340

Synthetic route

: 4-bromophenylboronic acid MIDA ester

: 98-80-6
phenylboronic acid

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 92-66-0
4-bromo-1,1'-biphenyl

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 5419-55-6
Triisopropyl borate

: 92-66-0
4-bromo-1,1'-biphenyl

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
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 tetrahydrofuran	1.53 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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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%

: 144432-80-4
2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
With boric acid In acetonitrile at 80℃; for 16h; Sealed tube;	32%

: 99-90-1
para-bromoacetophenone

: 98-80-6
phenylboronic acid

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
With C40H28N12Pd4S12; potassium carbonate In ethanol at 80℃; for 6h; Inert atmosphere;	8%

: 688-74-4
boric acid tributyl ester

: 3315-91-1
4-biphenylylmagnesium bromide

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
With diethyl ether at -70℃; und anschliessenden Hydrolyse;

: 1591-31-7
4-iodo-biphenyl

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
(i) nBuLi, (ii) B(OiBu)3, (iii) aq. HCl; Multistep reaction;

: 105123-35-1
2,4,6-tris([1,1'-biphenyl]-4-yl)boroxine

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
With water In chloroform-d1 at 25℃; Equilibrium constant; Thermodynamic data;

: C14H15BO2

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
With hydrogenchloride for 3h; pH=6 - 7;
With water; sodium hydroxide In tetrahydrofuran

: 150-46-9
triethyl borate

: 92-66-0
4-bromo-1,1'-biphenyl

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
Stage #1: 4-bromo-1,1'-biphenyl With tert.-butyl lithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: triethyl borate In tetrahydrofuran at -78 - 20℃; Further stages.;	800 mg

: 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate; water / tetrahydrofuran / 24 h / 18 °C / Inert atmosphere; Sealed tube 2: 2,3-dimethyl-2,3-butane diol; water / tetrahydrofuran / 1 h / 90 °C / Inert atmosphere View Scheme

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

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate; water / tetrahydrofuran / 24 h / 18 °C / Inert atmosphere; Sealed tube 2: 2,3-dimethyl-2,3-butane diol; water / tetrahydrofuran / 1 h / 90 °C / Inert atmosphere View Scheme

: 7732-18-5
water

: C14H15BO2

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 0.5h; Inert atmosphere;	1.82 g

: 5419-55-6
Triisopropyl borate

: C17H18O2Zn

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;

: 13675-18-8
tetrahydroxydiboron

: 92-66-0
4-bromo-1,1'-biphenyl

: 5122-94-1
4-biphenylboronic acid

Conditions

Conditions	Yield
With potassium tert-butylate In methanol at 0 - 20℃;

: 5122-94-1
4-biphenylboronic acid

: 135019-26-0
9,15-bis(trifluoromethylsulfonyloxy)<212,13><5.2>metacyclophane

: C45H40

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110 - 120℃; for 24h; Suzuki coupling reaction;	100%

: 5122-94-1
4-biphenylboronic acid

: 816458-62-5
6-bromo-5-isopropyl-3-methylpyrazine-2-carboxylic acid ethyl ester

: 6-(biphenyl-4-yl)-5-isopropyl-3-methylpyrazine-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In toluene at 90℃; for 1.5h; Suzuki coupling;	100%

: 5122-94-1
4-biphenylboronic acid

: 816458-63-6
6-bromo-5-isopropyl-3-phenylpyrazine-2-carboxylic acid ethyl ester

: 6-(biphenyl-4-yl)-5-isopropyl-3-phenylpyrazine-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In toluene at 90℃; Suzuki coupling;	100%

: 956319-50-9
trifluoro-methanesulfonic acid 3,5-dichloro-4-[3-(4,4-difluoro-piperidin-1-yl)-2-oxo-pyrrolidin-1-ylmethyl]-phenyl ester

: 5122-94-1
4-biphenylboronic acid

: 1-(3,5-dichloro-[1,1';4',1'']terphenyl-4-ylmethyl)-3-(4,4-difluoro-piperidin-1-yl)-pyrrolidin-2-one

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 80℃; for 1h; Suzuki Coupling;	100%

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 5122-94-1
4-biphenylboronic acid

: 144432-80-4
2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With potassium phosphate; water In tetrahydrofuran at 90℃; for 1h; Inert atmosphere;	100%
With air In dichloromethane at 25℃; for 16h; Molecular sieve;	46%
In diethyl ether at 20℃; Inert atmosphere; Molecular sieve;

: 865539-66-8
9,10-dimethyl-2,3,6,7,14,15-hexahydroxy-9,10-[1',2']benzenoanthracene

: 5122-94-1
4-biphenylboronic acid

: C58H39B3O6

Conditions

Conditions	Yield
In neat (no solvent) at 130℃; for 0.25h;	100%

: 1352002-20-0
10-(biphenyl-4-yl)-2-bromo-9,9-dimethyl-7-phenylacridan

: 5122-94-1
4-biphenylboronic acid

: 1403981-72-5
2,10-bis(biphenyl-4-yl)-9,9-dimethyl-7-phenylacridan

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 68℃; for 4h; Suzuki Coupling; Inert atmosphere;	100%

: 1333240-17-7
2-chloro-4,5-dimethoxypyrimidine

: 5122-94-1
4-biphenylboronic acid

: 2-(4-biphenyl)-4,5-dimethoxypyrimidine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water for 8h; Suzuki Coupling; Reflux; Inert atmosphere;	100%

: 1443986-20-6
2-(4-fluorophenyl)-3-iodo-6-(thien-3-yl)imidazo[1,2-a]pyridine

: 5122-94-1
4-biphenylboronic acid

: 3-(biphen-4-yl)-2-(4-fluorophenyl)-6-(thien-3-yl)imidazo[1,2-a]pyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 1h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	100%

: 25240-59-9
pinacolboronic acid

: 5122-94-1
4-biphenylboronic acid

: 144432-80-4
2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With potassium phosphate; water In tetrahydrofuran at 90℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%

: 4-bromo-1-(3-methoxyphenyl)-1-hydropyrazole

: 5122-94-1
4-biphenylboronic acid

: 4-(biphenyl-4-yl)-1-(3-methoxyphenyl)-1H-pyrazole

Conditions

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane; water at 95 - 105℃; for 20h; Inert atmosphere;	100%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane; water at 95 - 105℃; for 20h; Inert atmosphere;	100%

: 5122-94-1
4-biphenylboronic acid

: C25H27N3O3

: C35H31N3O

Conditions

Conditions	Yield
Stage #1: C25H27N3O3 With trichlorophosphate In toluene at 100℃; for 0.5h; Microwave irradiation; Stage #2: 4-biphenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 90℃; for 16h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃;	100%

: 40288-69-5
N-(2-cyanophenyl)benzamide

: 5122-94-1
4-biphenylboronic acid

: 4-([1,1'-biphenyl]-4-yl)-2-phenylquinazoline

Conditions

Conditions	Yield
With [2,2]bipyridinyl; lanthanum(III) acetate; trifluoroacetic acid In tetrahydrofuran at 20 - 70℃; for 22h; Reagent/catalyst; Temperature;	99.5%
With [2,2]bipyridinyl; palladium diacetate; trifluoroacetic acid In tetrahydrofuran at 80℃; for 24h; Schlenk technique;	95%

: 5122-94-1
4-biphenylboronic acid

: 117635-23-1
2,5-dibromo-1,4-di-N-dodecylbenzene

: 4-Bromo-2,5-didodecyl-[1,1';4',1'']terphenyl

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene for 72h; Heating;	99%

: 5122-94-1
4-biphenylboronic acid

: 841259-40-3
3-benzyloxy-4-iodo-5-(1-methoxycarbonyl-4-piperidyl)isoxazol

: 3-benzyloxy-4-(4-biphenyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide at 70℃; for 22h; Suzuki coupling;	99%

: 2446-83-5
di-isopropyl azodicarboxylate

: 5122-94-1
4-biphenylboronic acid

: 1,2-bis(isopropoxycarbonyl)-1-(biphenyl-4-yl)hydrazine

Conditions

Conditions	Yield
2,9-dimethyl-1,10-phenanthroline-based palladium(II) complex In 1,2-dichloro-ethane at 60℃; for 12h;	99%

: 1564-64-3
9-Bromoanthracene

: 5122-94-1
4-biphenylboronic acid

: 9-([1,1'-biphenyl]-4-yl)anthracene

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water at 80℃; for 17h; Inert atmosphere;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 24h; Inert atmosphere; Reflux; Sealed tube;	90%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 16h; Inert atmosphere;	90%

: 4122-56-9
methyl o-formylbenzoate

: 5122-94-1
4-biphenylboronic acid

: 135381-46-3
3-([1,1'-biphenyl]-4-yl)isobenzofuran-1(3H)-one

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); C27H30N2S(1+)*Cl(1-); cesium fluoride In toluene at 80℃; for 1h; Inert atmosphere;	99%

: 1202929-10-9
C11H8O3

: 5122-94-1
4-biphenylboronic acid

: C23H18O3

Conditions

Conditions	Yield
With [Pd(S,S)-bdpp(H2O)2](2+)(BF4(1-))2 In 1,4-dioxane at 20℃; for 0.416667h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

: 5122-94-1
4-biphenylboronic acid

: 92-69-3
4-Phenylphenol

Conditions

Conditions	Yield
With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide under 760.051 Torr; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Irradiation;	99%
With oxygen; triethylamine In acetonitrile at 20℃; under 760.051 Torr; for 4h; Reagent/catalyst; Irradiation;	99%
With dihydrogen peroxide In acetonitrile at 30 - 35℃; for 0.0833333h; Schlenk technique;	98%

: 930-68-7
cyclohexenone

: 5122-94-1
4-biphenylboronic acid

: 86921-83-7
3-([1,1’-biphenyl]-4-yl)cyclohexan-1-one

Conditions

Conditions	Yield
With 1,1'-dimesityl-3,3'-methylenediimidazolin-2,2'-diylidene-di(trifluoroacetato)palladium(II); potassium hydroxide In tetrahydrofuran; water at 20℃; for 36h;	99%
With potassium fluoride; C32H33ClO3P2Pd In toluene at 60℃; for 18h; Sealed tube; Inert atmosphere;	96%

: 1248340-80-8
2-phenyl-5-methyl-7-chlorobenzo[b]furan

: 5122-94-1
4-biphenylboronic acid

: 1335094-23-9
C27H20O

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 2h; Suzuki-Miyaura cross-coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 2h; Suzuki-Miyaura Coupling;	99%

: 1335094-11-5
7-chloro-2,5-diphenylbenzo[b]furan

: 5122-94-1
4-biphenylboronic acid

: 1335094-18-2
7-(biphenyl-4-yl)-2,5-diphenylbenzo[b]furan

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 2h; Suzuki-Miyaura cross-coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 2h; Suzuki-Miyaura Coupling;	99%

: 1335094-14-8
7-chloro-5-fluoro-2-phenylbenzo[b]furan

: 5122-94-1
4-biphenylboronic acid

: 1335094-28-4
7-(biphenyl-4-yl)-5-fluoro-2-phenylbenzo[b]furan

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 2h; Suzuki-Miyaura cross-coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 2h; Suzuki-Miyaura Coupling;	99%

: 118-48-9
isatoic anhydride

: 5122-94-1
4-biphenylboronic acid

: biphenyl-4-yl 2-aminobenzoate

Conditions

Conditions	Yield
With N-methylcyclohexylamine; tris-(dibenzylideneacetone)dipalladium(0); oxygen; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 60℃; for 24h;	99%

: 7633-38-7
di-tert-butyl fumarate

: 5122-94-1
4-biphenylboronic acid

: 1378314-25-0
(S)-di-tert-butyl-2-(biphenyl-4-yl)succinate

Conditions

Conditions	Yield
Stage #1: 4-biphenylboronic acid With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene; potassium tert-butylate In methanol; dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: di-tert-butyl fumarate In methanol; dichloromethane; isopropyl alcohol at 60℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

Yield

Stage #1: 4-biphenylboronic acid With chlorobis(ethylene)rhodium(I) dimer; (S,S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene; potassium tert-butylate In methanol; dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: di-tert-butyl fumarate In methanol; dichloromethane; isopropyl alcohol at 60℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

99%

: 92965-01-0
methyl 2-(2-oxo-2-phenylacetyl)benzoate

: 5122-94-1
4-biphenylboronic acid

: 1452219-94-1
3-([1,1'-biphenyl]-4-yl)-3-phenylisochroman-1,4-dione

Conditions

Conditions	Yield
Stage #1: methyl 2-(2-oxo-2-phenylacetyl)benzoate; 4-biphenylboronic acid With chlorobis(cyclooctene)rhodium(I) dimer; (R)-N-cinnamyl-2-methylpropane-2-sulfinamide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 3h; Stage #3: With sulfuric acid In tetrahydrofuran; methanol; water at 20℃; for 1h; enantioselective reaction;	99%

Yield

Stage #1: methyl 2-(2-oxo-2-phenylacetyl)benzoate; 4-biphenylboronic acid With chlorobis(cyclooctene)rhodium(I) dimer; (R)-N-cinnamyl-2-methylpropane-2-sulfinamide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 3h;
Stage #3: With sulfuric acid In tetrahydrofuran; methanol; water at 20℃; for 1h; enantioselective reaction;

99%

: 1422250-63-2
C18H15ClO4

: 5122-94-1
4-biphenylboronic acid

: 1422250-78-9
2-(7-(biphenyl-4-yl)-2-phenylbenzo[b]furan-5-yl)ethyl methyl carbonate

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 24h; Suzuki-Miyaura Coupling;	99%

: 1422250-61-0
7-chloro-2-pentyl-5-phenylbenzo[b]furan

: 5122-94-1
4-biphenylboronic acid

: 1422250-68-7
7-(biphenyl-4-yl)-2-pentyl-5-phenylbenzo[b]furan

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 2h; Suzuki-Miyaura Coupling;	99%

: 1422250-62-1
7-chloro-5-methyl-2-phenethylbenzo[b]furan

: 5122-94-1
4-biphenylboronic acid

: 1422250-73-4
7-(biphenyl-4-yl)-5-methyl-2-phenethylbenzo[b]furan

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 2h; Suzuki-Miyaura Coupling;	99%

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^-24cm³; (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

Product Name

4-Biphenylboronic acid

Synthetic route

4-Biphenylboronic acid Specification

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