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768-35-4

Basic Information
CAS No.: 768-35-4
Name: 3-Fluorophenylboronic acid
Molecular Structure:
Molecular Structure of 768-35-4 (3-Fluorophenylboronic acid)
Formula: C6H6BFO2
Molecular Weight: 139.92
Synonyms: (3-fluorophenyl)boronic acid
EINECS: 476-720-8
Density: 1.24 g/cm3
Melting Point: 214-218 °C(lit.)
Boiling Point: 271.4 °C at 760 mmHg
Flash Point: 117.9 °C
Solubility:
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 36/37/38-22
Safety: 22-24/25-37/39-26-36
Transport Information:
PSA: 40.46000
LogP: -0.49450
Synthetic route
625-98-9

3-chlorofluorobenzene

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
95%
1073-06-9

3-fluorobromobenzene

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
Stage #1: 3-fluorobromobenzene With diisobutylaluminium hydride; magnesium; lithium chloride In tetrahydrofuran; toluene at 20℃; for 15h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; toluene at 0℃; Inert atmosphere;
83%
Stage #1: 3-fluorobromobenzene With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 1.5h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; toluene at -78 - 20℃; for 1h; Inert atmosphere;
70%
Stage #1: 3-fluorobromobenzene With magnesium In diethyl ether Grignard reaction;
Stage #2: With Trimethyl borate In diethyl ether at 3℃; for 3h; boronation;
Stage #3: With hydrogenchloride In diethyl ether Hydrolysis;
13675-18-8

tetrahydroxydiboron

1073-06-9

3-fluorobromobenzene

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
In methanol at 15℃; for 3h; Microwave irradiation;83%
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran; methanol at 50 - 55℃; Inert atmosphere;85 %Chromat.
5419-55-6

Triisopropyl borate

1-halo-3-fluorobenzene

1-halo-3-fluorobenzene

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; water; toluene at -78 - 20℃; Inert atmosphere; Schlenk technique;80%
372-19-0

meta-fluoroaniline

13675-18-8

tetrahydroxydiboron

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
Stage #1: meta-fluoroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: tetrahydroxydiboron With sodium acetate In water at 20℃; for 0.333333h;
67%
5419-55-6

Triisopropyl borate

1073-06-9

3-fluorobromobenzene

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
Stage #1: 3-fluorobromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 0.833333h; Inert atmosphere;
65%
13675-18-8

tetrahydroxydiboron

1996-38-9

3-fluorobenzenediazonium tetrafluoroborate

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 0.25h;59%
688-74-4

boric acid tributyl ester

3-fluoro-phenyl magnesium bromide

3-fluoro-phenyl magnesium bromide

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
With diethyl ether und anschliessenden Hydrolyse;
121-43-7

Trimethyl borate

1073-06-9

3-fluorobromobenzene

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran N2; BuLi dropping into org. compd. soln. at -78°C, mixt. keeping 3 h, B-compd. soln. addn. dropwise at -78°C, mixt. allowing to warm to room temp. overnight , stirring 1 h with 10% HCl, extn. (Et2O); org. extracts washing (water), drying, solvent vac. removal;
With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
688-74-4

boric acid tributyl ester

17318-03-5

bromo(3-fluorophenyl)magnesium

768-35-4

3-fluorophenylboronic acid

C8H10BFO2

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; Inert atmosphere; Schlenk technique;
372-19-0

meta-fluoroaniline

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water / 0.03 h / 20 °C
1.2: 0.25 h / 0 °C
2.1: N,N-dimethyl-formamide / 0.25 h / 20 °C
View Scheme
5419-55-6

Triisopropyl borate

C11H13FO2Zn

768-35-4

3-fluorophenylboronic acid

Conditions
ConditionsYield
With copper(I) iodide-lithium chloride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;
768-35-4

3-fluorophenylboronic acid

110526-62-0

2',3',5'-tris-O-(tert-butyldimethylsilyl)-2'-deoxyinosine

864847-17-6

N1-(3-fluorophenyl)-2',3',5'-tris-(O-tert-butyldimethylsilyl)-inosine

Conditions
ConditionsYield
With pyridine; pyridine N-oxide; oxygen; 4 A molecular sieve; copper diacetate In dichloromethane at 20℃; under 760 Torr; for 24h;100%
With pyridine; pyridine N-oxide; oxygen; copper diacetate In dichloromethane at 20℃; for 24h; 4Å molecular sieves;67%
768-35-4

3-fluorophenylboronic acid

126-30-7

2,2-Dimethyl-1,3-propanediol

2-(3-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Conditions
ConditionsYield
With magnesium sulfate In diethyl ether at 20℃; for 20h;100%
In toluene at 20℃; for 2h;55%
In benzene Reflux;
In toluene at 20℃; for 12h;
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;
25026-64-6

3-chloro-5-fluoro-benzoic acid

768-35-4

3-fluorophenylboronic acid

1214352-53-0

3-fluoro-5-(3-fluorophenyl)benzoic acid

Conditions
ConditionsYield
Stage #1: 3-chloro-5-fluoro-benzoic acid; 3-fluorophenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; potassium carbonate; palladium diacetate In water at 20℃; for 96h; Inert atmosphere;
Stage #2: With hydrogenchloride In water pH=4;
100%
768-35-4

3-fluorophenylboronic acid

202982-72-7

4-chloro-3-iodophenol

1354787-35-1

6-chloro-3'-fluorobiphenyl-3-ol

Conditions
ConditionsYield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 70℃; for 5h; Suzuki Coupling; Inert atmosphere;100%
1263795-03-4

tert-butyl 8-bromo-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate

768-35-4

3-fluorophenylboronic acid

1263795-09-0

tert-butyl 8-(3-fluorophenyl)-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 100℃; for 12h; Inert atmosphere;100%
5613-27-4

5-bromo-2,3-dimethyl-benzoic acid

768-35-4

3-fluorophenylboronic acid

1427407-47-3

5-bromo-2,3-dimethyl-benzoic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 95℃; Inert atmosphere;100%
14804-38-7

5-bromo-2-methoxy-1,3-dimethylbenzene

768-35-4

3-fluorophenylboronic acid

C15H15FO

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 70℃; for 18h; Inert atmosphere;100%
With potassium phosphate; C43H47Cl3N4O2Pd In N,N-dimethyl-formamide at 80℃; for 22h; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Schlenk technique;
768-35-4

3-fluorophenylboronic acid

tert-butyl ((1S,4s)-4-((6-chloro-2-(((R)-1-methoxypropan-2-yl)amino)pyrido[3,2-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

tert-butyl ((1S,4s)-4-((6-(3-fluorophenyl)-2-(((R)-1-methoxypropan-2-yl)amino)pyrido[3,2-d]pyrimidin-4-yl)amino)cyclohexyl)carbamate

Conditions
ConditionsYield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 130℃; for 0.5h; Microwave irradiation;100%
1355483-74-7

2-(4-bromophenyl)-5,6,7-trimethoxy-4H-chromen-4-one

768-35-4

3-fluorophenylboronic acid

C24H19FO5

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 120℃; Inert atmosphere;100%
1003-98-1

2-bromo-4-fluoroaniline

768-35-4

3-fluorophenylboronic acid

3',5-difluoro-[1,1'-biphenyl]-2-amine

Conditions
ConditionsYield
With palladium diacetate; diisopropylamine In water at 100℃; for 0.5h; Suzuki-Miyaura Coupling;100%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;
1279123-63-5

potassium hydrogenfluoride

768-35-4

3-fluorophenylboronic acid

potassium 3-fluorophenyl trifluoroborate

Conditions
ConditionsYield
In methanol; water for 0.5h;100%
In diethyl ether; water at 20℃; for 3h;99%
1312684-68-6

7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate

768-35-4

3-fluorophenylboronic acid

8-(3-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere;100%

5-bromo-3-isopropyl(trans-4-methylcyclohexylcarbonyl)amino-thiophene-2-carboxylic acid methyl ester

768-35-4

3-fluorophenylboronic acid

5-(3-fluoro-phenyl)-3-[isopropyl-(4-methyl-cyclohexanecarbonyl)-amino]-thiphene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene at 70℃; for 18h; Heating / reflux;99%

5-acetyl-4-[(3,5-dichlorophenyl)amino]-2-ethyl-6-phenylpyridazin-3(2H)-one

768-35-4

3-fluorophenylboronic acid

5-acetyl-4-[N-(3,5-dichlorophenyl)-N-(3-fluorophenyl)amino]-2-ethyl-6-phenylpyridazin-3(2H)-one

Conditions
ConditionsYield
With oxygen; copper diacetate; triethylamine In dichloromethane at 20℃; for 72h; Molecular sieve;99%
768-35-4

3-fluorophenylboronic acid

64794-30-5

N-(3-tert-butylphenyl)-2-chloronicotinamide

1231732-11-8

N-(3-tert-butylphenyl)-2-(3-fluorophenyl)nicotinamide

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 3h; Inert atmosphere;99%
1312686-23-9

6-acetyl-4-chloro-2-cyano-3-methylphenyl trifluoromethanesulfonate

768-35-4

3-fluorophenylboronic acid

1312686-24-0

6-acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 80℃; for 2h;99%
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 80℃; for 2h; Inert atmosphere;99%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In water; toluene at 80℃; for 2h; Inert atmosphere;98.5%

4-bromo-13,15-dimethyl-14-oxa-10,15-diazatetracyclo[8.7.0.0(2,7).0(12,16)]heptadeca-2,4,6-trien-11-one

768-35-4

3-fluorophenylboronic acid

C22H23FN2O2

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); caesium carbonate In 1,4-dioxane at 100℃; Suzuki coupling;99%
930-88-1

N-methylmaleimide

768-35-4

3-fluorophenylboronic acid

1314427-25-2

(R)-3-(3-fluorophenyl)-1-methyl-2,5-pyrrolidinedione

Conditions
ConditionsYield
With [Rh(OH)(cod)]2; (R)-MeO-F12-BIPHEP In diethyl ether; water at 0℃; for 36h; Schlenk technique; Inert atmosphere;99%
1611473-65-4

8-bromo-N-(2-(methylsulfonyl)ethyl)-1,6-naphthyridine-2-carboxamide

768-35-4

3-fluorophenylboronic acid

1611473-13-2

8-(3-fluorophenyl)-N-(2-(methylsulfonyl)ethyl)-1,6-naphthyridine-2-carboxamide

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 3h;99%

3-amino-N-(6-chloropyridin-3-yl)-4-(trifluoromethoxy)benzamide

768-35-4

3-fluorophenylboronic acid

3-amino-N-[6-(3-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; Inert atmosphere; Sealed tube;99%
768-35-4

3-fluorophenylboronic acid

54450-20-3

5-bromo-3(2H)-benzofuranone

5-(3-fluorophenyl)benzofuran-3(2H)-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In toluene at 80℃; Schlenk technique; Inert atmosphere; Sealed tube;99%

2-methylbenzyl carbamate

768-35-4

3-fluorophenylboronic acid

C14H13F

Conditions
ConditionsYield
With NHC-Pd(II)-Im; lithium tert-butoxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;99%
768-35-4

3-fluorophenylboronic acid

84640-24-4

4-methoxybenzyl N,N-dimethylcarbamate

1-fluoro-3-(4-methoxybenzyl)benzene

Conditions
ConditionsYield
With NHC-Pd(II)-Im; lithium tert-butoxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;99%
16605-27-9

3-methylbenzyl N,N-dimethylcarbamate

768-35-4

3-fluorophenylboronic acid

C14H13F

Conditions
ConditionsYield
With NHC-Pd(II)-Im; lithium tert-butoxide In water at 80℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;99%
89488-29-9

2-bromo-4-methoxypyridine

768-35-4

3-fluorophenylboronic acid

2-(3-fluorophenyl)-4-methoxypyridine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 85℃; Inert atmosphere;99%
768-35-4

3-fluorophenylboronic acid

ethyl 4-bromo-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-isopropyl-1H-pyrazole-5-carboxylate

ethyl 1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-4-(3-fluorophenyl)-3-isopropyl-1H-pyrazole-5-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 85℃; for 16h; Inert atmosphere; Sealed tube;99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 20 - 85℃; for 16h; Inert atmosphere; Sealed tube;99%
768-35-4

3-fluorophenylboronic acid

717-41-9

2-benzyl-1,2,6-thiadiazine 1,1-dioxide

(S)-6-benzyl-3-(3-fluorophenyl)-3,6-dihydro-2H-1,2,6-thiadiazine 1,1-dioxide

Conditions
ConditionsYield
Stage #1: 3-fluorophenylboronic acid; 2-benzyl-1,2,6-thiadiazine 1,1-dioxide With chlorobis(cyclooctene)rhodium(I) dimer; C18H23NOS In toluene at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With potassium hydroxide In water; toluene at 60℃; Inert atmosphere; enantioselective reaction;
99%
768-35-4

3-fluorophenylboronic acid

144511-93-3

2-chloro-N-phenylquinazolin-4-amine

1304764-81-5

4-anilino-2-(3-fluorophenyl)quinazoline

Conditions
ConditionsYield
With C34H48Cl2N4Pd; potassium hydroxide In ethanol at 60℃; for 36h; Inert atmosphere;99%
With NHC-Pd(II)-Im; potassium hydroxide In ethanol at 20℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique;98%
768-35-4

3-fluorophenylboronic acid

C19H17NO3

C25H22FNO3

Conditions
ConditionsYield
With nickel(II) acetate tetrahydrate; (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol In 2,2,2-trifluoroethanol at 80℃; for 24h; enantioselective reaction;99%
5325-66-6, 20890-12-4, 72491-18-0

1-phenyl-3-(2-pyridyl)propen-1-one

768-35-4

3-fluorophenylboronic acid

(S)-3-(3-fluorophenyl)-1-phenyl-3-(pyridin-2-yl)propan-1-one

Conditions
ConditionsYield
With (R)-(+)-(4,4'-bi-1,3-benzodioxole)-5,5'-diylbis(di(3,5-dimethylphenyl)phosphine); di-μ-chloro-bis[bis(cyclo-octene)rhodium]; potassium hydroxide In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction;99%
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    3-Fluorophenylboronic acid

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    3-Fluorophenylboronic acid

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    768-35-4 3-Fluorophenylboronic acid

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Chemistry

Molecular structure of 3-Fluorophenylboronic acid (CAS NO.768-35-4) is:

Product Name: 3-Fluorophenylboronic acid
CAS Registry Number: 768-35-4
IUPAC Name: (3-Fluorophenyl)boronic acid
Molecular Weight: 139.920043 [g/mol]
Molecular Formula: C6H6BFO2
H-Bond Donor: 2
H-Bond Acceptor: 3
Melting Point: 214-218 °C(lit.)
storage temp. 0-6 °C
Surface Tension: 38.6 dyne/cm
Density: 1.24 g/cm3
Flash Point: 117.9 °C
Enthalpy of Vaporization: 53.83 kJ/mol
Boiling Point: 271.4 °C at 760 mmHg
Vapour Pressure: 0.00318 mmHg at 25°C
Product Categories: blocks; BoronicAcids; FluoroCompounds; Boronic Acid series; Fluoro-Aromatics; Boron, Nitrile, Thio,& TM-Cpds; Substituted Boronic Acids; Boronic Acids & Esters; Phenyls & Phenyl-Het; Fluorobenzene; Heterocyclic Compounds; Boronic Acid; Aryl; Fluorinated; Organoborons; B (Classes of Boron Compounds); Boronic Acids; Chiral chemicals; Boronic Acids & Esters; Phenyls & Phenyl-Het

Uses

 3-Fluorophenylboronic acid (CAS NO.768-35-4) is used as intermediates of Liquid Crystals.

Safety Profile

Safty information about 3-Fluorophenylboronic acid (CAS NO.768-35-4) is:
Hazard Codes: HarmfulXn,Xi
Risk Statements: 36/37/38-22 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R22:Harmful if swallowed.
Safety Statements: 22-24/25-37/39-26-36 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes. 
S37/39:Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
Hazard Note: Irritant
HazardClass: IRRITANT

Specification

 3-Fluorophenylboronic acid , its cas register number is 768-35-4. It also can be called 3-Fluorobenzeneboronic acid . It is a white to light yellow crystal powder.