5122-94-1

Basic information

• Product Name: 4-Biphenylboronic acid
• Synonyms: RARECHEM AH PB 0261;(1,1'-BIPHENYL-4-YL)BORONIC ACID;AKOS BRN-0030;4-PHENYLBENZENEBORONIC ACID;4-PHENYLPHENYLBORONIC ACID;4-BIPHENYLBORONIC ACID;4-BIPHENYLYLBORONIC ACID;BIPHENYL-4-BORONIC ACID
• CAS NO: 5122-94-1
• Molecular Formula: C₁₂H₁₁BO₂
• Molecular Weight: 198.03
• EINECS: -0
• Product Categories: Boron Compounds;blocks;BoronicAcids;Substituted Boronic Acids;Boronic acid;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic acid series;Aryl;Boronic Acids;Boronic Acids and Derivatives
• Mol File: 5122-94-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 232-245 °C(lit.)
• Boiling Point: 385.504 °C at 760 mmHg
• Flash Point: 186.946 °C
• Appearance: White/Powder
• Density: 1.184 g/cm³
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Acetone,Methanol
• PKA: 8.61±0.10(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 2937410
• CAS DataBase Reference: 4-Biphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Biphenylboronic acid(5122-94-1)
• EPA Substance Registry System: 4-Biphenylboronic acid(5122-94-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36-24/25
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 5122-94-1(Hazardous Substances Data)

Usage

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 5122-94-1 differently. You can refer to the following data:
1. suzuki reaction: Suzuki coupling of 2-(4-bromophenyl)thiophene with phenylboronic acid and 4-biphenylboronic acid are used for the preparation of 4-(2-thieny)biphenyl and 4-(2-thienyl)-1,1':4,1''-biphenyl respectively. Coupling of two equivalents of 4-(2-thienyl)phenylboronic acid with 1,4-diiodobenzene gives 4,4''-bis(2-thienyl)-1,1':4,1''-terphenyl and with 2,5-diiodothiophene, 2,5-bis[4-(2-thienyl)-phenyl]-thiophene is obtained.
2. Used in Suzuki reactions and as intermediates of liquid crystals.

InChI:InChI=1/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15H

Synthetic route

4-bromophenylboronic acid MIDA ester + phenylboronic acid (98-80-6) → 4-biphenylboronic acid (5122-94-1)

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%

Trimethyl borate (121-43-7) + 4-bromo-1,1'-biphenyl (92-66-0) → 4-biphenylboronic acid (5122-94-1)

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+) + phenylboronic acid (98-80-6) → 4-biphenylboronic acid (5122-94-1)

Conditions	Yield
With potassium carbonate In ethanol; water at 50℃; for 5h; Inert atmosphere;	86%

Triisopropyl borate (5419-55-6) + 4-bromo-1,1'-biphenyl (92-66-0) + water (7732-18-5) → 4-biphenylboronic acid (5122-94-1)

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%

4-bromo-1,1'-biphenyl (92-66-0) → 4-biphenylboronic acid (5122-94-1)

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%

methanol (67-56-1) + diisopropylamine borane (55124-35-1) + 4-bromo-1,1'-biphenyl (92-66-0) → 4-biphenylboronic acid (5122-94-1)

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%

Triisopropyl borate (5419-55-6) + 4-bromo-1,1'-biphenyl (92-66-0) → 4-biphenylboronic acid (5122-94-1)

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%)

2-([1,1'-biphenyl]-4-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (1104636-67-0) → 4-biphenylboronic acid (5122-94-1)

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

boric acid tributyl ester (688-74-4) + 4-bromo-1,1'-biphenyl (92-66-0) + water (7732-18-5) → 4-biphenylboronic acid (5122-94-1)

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%

2-(4-bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione + phenylboronic acid (98-80-6) → 4-biphenylboronic acid (5122-94-1)

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%

2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (144432-80-4) → 4-biphenylboronic acid (5122-94-1)

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

para-bromoacetophenone (99-90-1) + phenylboronic acid (98-80-6) → 4-biphenylboronic acid (5122-94-1)

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

boric acid tributyl ester (688-74-4) + 4-biphenylylmagnesium bromide (3315-91-1) → 4-biphenylboronic acid (5122-94-1)

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

4-iodo-biphenyl (1591-31-7) → 4-biphenylboronic acid (5122-94-1)

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

2,4,6-tris([1,1'-biphenyl]-4-yl)boroxine (105123-35-1) → 4-biphenylboronic acid (5122-94-1)

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

C14H15BO2 → 4-biphenylboronic acid (5122-94-1)

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

triethyl borate (150-46-9) + 4-bromo-1,1'-biphenyl (92-66-0) → 4-biphenylboronic acid (5122-94-1)

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

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 4-biphenylboronic acid (5122-94-1)

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 → 4-biphenylboronic acid (5122-94-1)

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

water (7732-18-5) + C14H15BO2 → 4-biphenylboronic acid (5122-94-1)

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

Triisopropyl borate (5419-55-6) + C17H18O2Zn → 4-biphenylboronic acid (5122-94-1)

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

tetrahydroxydiboron (13675-18-8) + 4-bromo-1,1'-biphenyl (92-66-0) → 4-biphenylboronic acid (5122-94-1)

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

4-biphenylboronic acid (5122-94-1) + 9,15-bis(trifluoromethylsulfonyloxy)<212,13><5.2>metacyclophane (135019-26-0) → C45H40

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

4-biphenylboronic acid (5122-94-1) + 6-bromo-5-isopropyl-3-methylpyrazine-2-carboxylic acid ethyl ester (816458-62-5) → 6-(biphenyl-4-yl)-5-isopropyl-3-methylpyrazine-2-carboxylic acid ethyl ester

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

4-biphenylboronic acid (5122-94-1) + 6-bromo-5-isopropyl-3-phenylpyrazine-2-carboxylic acid ethyl ester (816458-63-6) → 6-(biphenyl-4-yl)-5-isopropyl-3-phenylpyrazine-2-carboxylic acid ethyl ester

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

trifluoro-methanesulfonic acid 3,5-dichloro-4-[3-(4,4-difluoro-piperidin-1-yl)-2-oxo-pyrrolidin-1-ylmethyl]-phenyl ester (956319-50-9) + 4-biphenylboronic acid (5122-94-1) → 1-(3,5-dichloro-[1,1';4',1'']terphenyl-4-ylmethyl)-3-(4,4-difluoro-piperidin-1-yl)-pyrrolidin-2-one

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

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-biphenylboronic acid (5122-94-1) → 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (144432-80-4)

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;

9,10-dimethyl-2,3,6,7,14,15-hexahydroxy-9,10-[1',2']benzenoanthracene (865539-66-8) + 4-biphenylboronic acid (5122-94-1) → C58H39B3O6

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

10-(biphenyl-4-yl)-2-bromo-9,9-dimethyl-7-phenylacridan (1352002-20-0) + 4-biphenylboronic acid (5122-94-1) → 2,10-bis(biphenyl-4-yl)-9,9-dimethyl-7-phenylacridan (1403981-72-5)

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

2-chloro-4,5-dimethoxypyrimidine (1333240-17-7) + 4-biphenylboronic acid (5122-94-1) → 2-(4-biphenyl)-4,5-dimethoxypyrimidine

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

2-(4-fluorophenyl)-3-iodo-6-(thien-3-yl)imidazo[1,2-a]pyridine (1443986-20-6) + 4-biphenylboronic acid (5122-94-1) → 3-(biphen-4-yl)-2-(4-fluorophenyl)-6-(thien-3-yl)imidazo[1,2-a]pyridine

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%

pinacolboronic acid (25240-59-9) + 4-biphenylboronic acid (5122-94-1) → 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (144432-80-4)

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 + 4-biphenylboronic acid (5122-94-1) → 4-(biphenyl-4-yl)-1-(3-methoxyphenyl)-1H-pyrazole

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%

4-biphenylboronic acid (5122-94-1) + C25H27N3O3 → C35H31N3O

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%

N-(2-cyanophenyl)benzamide (40288-69-5) + 4-biphenylboronic acid (5122-94-1) → 4-([1,1'-biphenyl]-4-yl)-2-phenylquinazoline

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%

4-biphenylboronic acid (5122-94-1) + 2,5-dibromo-1,4-di-N-dodecylbenzene (117635-23-1) → 4-Bromo-2,5-didodecyl-[1,1';4',1'']terphenyl

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

4-biphenylboronic acid (5122-94-1) + 3-benzyloxy-4-iodo-5-(1-methoxycarbonyl-4-piperidyl)isoxazol (841259-40-3) → 3-benzyloxy-4-(4-biphenyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole

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

di-isopropyl azodicarboxylate (2446-83-5) + 4-biphenylboronic acid (5122-94-1) → 1,2-bis(isopropoxycarbonyl)-1-(biphenyl-4-yl)hydrazine

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

9-Bromoanthracene (1564-64-3) + 4-biphenylboronic acid (5122-94-1) → 9-([1,1'-biphenyl]-4-yl)anthracene

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%

methyl o-formylbenzoate (4122-56-9) + 4-biphenylboronic acid (5122-94-1) → 3-([1,1'-biphenyl]-4-yl)isobenzofuran-1(3H)-one (135381-46-3)

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

C11H8O3 (1202929-10-9) + 4-biphenylboronic acid (5122-94-1) → C23H18O3

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%

4-biphenylboronic acid (5122-94-1) → 4-Phenylphenol (92-69-3)

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%

cyclohexenone (930-68-7) + 4-biphenylboronic acid (5122-94-1) → 3-([1,1’-biphenyl]-4-yl)cyclohexan-1-one (86921-83-7)

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%

2-phenyl-5-methyl-7-chlorobenzo[b]furan (1248340-80-8) + 4-biphenylboronic acid (5122-94-1) → C27H20O (1335094-23-9)

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%

7-chloro-2,5-diphenylbenzo[b]furan (1335094-11-5) + 4-biphenylboronic acid (5122-94-1) → 7-(biphenyl-4-yl)-2,5-diphenylbenzo[b]furan (1335094-18-2)

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%

7-chloro-5-fluoro-2-phenylbenzo[b]furan (1335094-14-8) + 4-biphenylboronic acid (5122-94-1) → 7-(biphenyl-4-yl)-5-fluoro-2-phenylbenzo[b]furan (1335094-28-4)

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%

isatoic anhydride (118-48-9) + 4-biphenylboronic acid (5122-94-1) → biphenyl-4-yl 2-aminobenzoate

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

di-tert-butyl fumarate (7633-38-7) + 4-biphenylboronic acid (5122-94-1) → (S)-di-tert-butyl-2-(biphenyl-4-yl)succinate (1378314-25-0)

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%

methyl 2-(2-oxo-2-phenylacetyl)benzoate (92965-01-0) + 4-biphenylboronic acid (5122-94-1) → 3-([1,1'-biphenyl]-4-yl)-3-phenylisochroman-1,4-dione (1452219-94-1)

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%

C18H15ClO4 (1422250-63-2) + 4-biphenylboronic acid (5122-94-1) → 2-(7-(biphenyl-4-yl)-2-phenylbenzo[b]furan-5-yl)ethyl methyl carbonate (1422250-78-9)

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%

7-chloro-2-pentyl-5-phenylbenzo[b]furan (1422250-61-0) + 4-biphenylboronic acid (5122-94-1) → 7-(biphenyl-4-yl)-2-pentyl-5-phenylbenzo[b]furan (1422250-68-7)

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%

7-chloro-5-methyl-2-phenethylbenzo[b]furan (1422250-62-1) + 4-biphenylboronic acid (5122-94-1) → 7-(biphenyl-4-yl)-5-methyl-2-phenethylbenzo[b]furan (1422250-73-4)

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%

Upstream product

• 688-74-4 boric acid tributyl ester 
• 3315-91-1 4-biphenylylmagnesium bromide 
• 121-43-7 Trimethyl borate 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 105123-35-1 2,4,6-tris([1,1'-biphenyl]-4-yl)boroxine 
• 144432-80-4 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 7732-18-5 water 
• 13675-18-8 tetrahydroxydiboron 
• 99-90-1 para-bromoacetophenone 
• 98-80-6 phenylboronic acid 
• 67-56-1 methanol 
• 55124-35-1 diisopropylamine borane 
• 5419-55-6 Triisopropyl borate 
• 1104636-67-0 2-([1,1'-biphenyl]-4-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione 

Downstream Products

• 92-94-4 [1,1';4',1'']terphenyl 
• 175850-28-9 5,5'-di([1,1'-biphenyl]-4-yl)-2,2'-bithiophene 
• 374625-46-4 1,2-Bis[6-(4-biphenyl)-2-methyl-1-benzothiophen-3-yl]hexafluorocyclopentene 
• 13476-68-1 1,1':4',1'':3'',1''':4''',1''''-quinquephenyl 
• 3073-05-0 penta-p-phenylene 
• 1762-84-1 4-bromo-p-terphenyl 
• 93214-88-1 8-biphenyl-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione 
• 677297-95-9 7-Biphenyl-4-yl-benzo[1,2,4]triazin-3-ylamine 
• 41373-29-9 5-([1,1'-biphenyl]-4-yl)furan-2-carbaldehyde 

Relevant articles and documents

Emission enhancement by formation of aggregates in hybrid chromophoric surfactant amphiphile/silica nanocomposites

(Figure Presented) In best order: Nanoaggregates of chromophores formed in a controlled fashion in self-assembled functional hybrid nanocomposites enhance fluorescence (see scheme). These hybrids minimize the problem of solid-state quenching and are thus applicable in the fabrication of electroluminescence devices.

Nitrogen-containing compound, electronic element, and electronic device

The invention provides a nitrogen-containing compound shown as a chemical formula 1, an electronic element and an electronic device, and belongs to the technical field of organic materials. The structural formula of the nitrogen-containing compound is shown as a chemical formula 1, wherein Ar1 and Ar2 are selected from substituted or unsubstituted aryl with the carbon atom number of 6-30, substituted or unsubstituted heteroaryl with the carbon atom number of 3-30 and substituted or unsubstituted naphthenic base with the carbon atom number of 3-20; Ar3 is selected from substituted or unsubstituted aryl with the carbon atom number of 6-20 and substituted or unsubstituted heteroaryl with the carbon atom number of 3-20.

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.