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Biphenyl-3-boronic acid

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Name

Biphenyl-3-boronic acid

EINECS -0
CAS No. 5122-95-2 Density 1.18 g/cm3
PSA 40.46000 LogP 1.03340
Solubility Insoluble in water. Melting Point 193-198 °C(lit.)
Formula C12H11BO2 Boiling Point 411 °C at 760 mmHg
Molecular Weight 198.029 Flash Point 202.3 °C
Transport Information N/A Appearance yellow crystal powder
Safety 37/39-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 5122-95-2 (Biphenyl-3-boronic acid) Hazard Symbols IrritantXi,CorrosiveC
Synonyms

Biphenyl-3-bronic acid;biphenyl-3-ylboronic acid;3-Biphenylboronic acid;

Article Data 12

Biphenyl-3-boronic acid Synthetic route

121-43-7

Trimethyl borate

2113-57-7

3-bromobiphenyl

5122-95-2

3-Biphenylboronic acid

Conditions
ConditionsYield
Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran at 20℃; for 2h; Further stages.;
75%
With hydrogenchloride; n-butyllithium In tetrahydrofuran soln. of n-BuLi in hexanes added dropwise to soln. of biphenyl compd. at-78°C under Ar, kept at this temp. for 2 h, soln. of borate adde d over 30 min, allowed to warm to room temp. overnight, 10% aq. HCl added, stirred for 2 h at room temp.; extd. into Et2O, washed with concd. soln. of Na2CO3 then with H2O, evapd., recrystd. twice from H2O/EtOH (95/5);75%
Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran; hexane for 24h;
65%
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;43%
With hydrogenchloride; tert.-butyl lithium In water; pentane
2113-57-7

3-bromobiphenyl

5122-95-2

3-Biphenylboronic acid

Conditions
ConditionsYield
Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 4h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 2h;
55%
Multi-step reaction with 2 steps
1.1: n-BuLi / -78 °C
1.2: -78 - 20 °C
2.1: aq. HCl
View Scheme
Stage #1: 3-bromobiphenyl With magnesium In tetrahydrofuran
Stage #2: With Trimethyl borate
Stage #3: With hydrogenchloride Further stages.;
121-43-7

Trimethyl borate

92-66-0

4-bromo-1,1'-biphenyl

5122-95-2

3-Biphenylboronic acid

Conditions
ConditionsYield
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%
688-74-4

boric acid tributyl ester

103068-18-4

[(1,1'-biphenyl)-3-yl]magnesium bromide

5122-95-2

3-Biphenylboronic acid

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

C18H23BO2

5122-95-2

3-Biphenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride
108-36-1

1,3-dibromobenzene

5122-95-2

3-Biphenylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Pd(PPh3)4; Na2CO3 / 1,2-dimethoxy-ethane / 80 °C
2.1: n-BuLi / -78 °C
2.2: -78 - 20 °C
3.1: aq. HCl
View Scheme
Multi-step reaction with 2 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 3 h / 90 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
2.2: 24 h
View Scheme
98-80-6

phenylboronic acid

polymer; monomer(s): Actitex 1500-1, modified with [BF4][4-N2C6H4CH2Cl]; 4-halogenobenzenethiol

polymer; monomer(s): Actitex 1500-1, modified with [BF4][4-N2C6H4CH2Cl]; 4-halogenobenzenethiol

5122-95-2

3-Biphenylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Pd(PPh3)4; Na2CO3 / 1,2-dimethoxy-ethane / 80 °C
2.1: n-BuLi / -78 °C
2.2: -78 - 20 °C
3.1: aq. HCl
View Scheme
5419-55-6

Triisopropyl borate

2113-57-7

3-bromobiphenyl

5122-95-2

3-Biphenylboronic acid

Conditions
ConditionsYield
Stage #1: 3-bromobiphenyl With n-butyllithium In diethyl ether; hexane; toluene at -30 - 0℃; for 1h;
Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -70 - 20℃; for 1h;
Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene
With tert.-butyl lithium In diethyl ether; pentane
98-80-6

phenylboronic acid

5122-95-2

3-Biphenylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 3 h / 90 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
2.2: 24 h
View Scheme
1394235-81-4

9-bromo-N-(tert-butyl)-3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine

5122-95-2

3-Biphenylboronic acid

1410123-84-0

9-[(1-1’-biphenyl)-3-yl]-N-(tert-butyl)-3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; water; toluene for 1h; Suzuki-Miyaura Coupling; Reflux;100%

Biphenyl-3-boronic acid Chemical Properties

MF: C12H11BO2
MW: 198.03
Mol File: 5122-95-2.mol 
mp:  193-198 °C(lit.)
storage temp:.  0-6°C
BRN : 2836311
CAS DataBase Reference: 5122-95-2(CAS DataBase Reference)

Biphenyl-3-boronic acid Toxicity Data With Reference

1、RTECS#: CAS# 5122-95-2: None listed
2、LD50/LC50: RTECS: Not available. 
3、Carcinogenicity: Biphenyl-3-boronic acid - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
4、Other: The toxicological properties have not been fully investigated.

Biphenyl-3-boronic acid Safety Profile

Hazard Codes:  Xi,C
Risk Statements:  36/37/38
Safety Statements:  37/39-26
WGK Germany:  3
Hazard Note:  Corrosive

Biphenyl-3-boronic acid Specification

(1):Handling and Storage of 3-BIPHENYLBORONIC ACID
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and   eyes. 
Storage: Store in a tightly closed container. Store in a dry area. Keep refrigerated(Store below 4°C/39°F.)
(2):Fire Fighting Measures of 3-BIPHENYLBORONIC ACID  
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. 
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 

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