768-35-4

Basic information

• Product Name: 3-Fluorophenylboronic acid
• Synonyms: AKOS BRN-0105;3-FLUOROBENZENEBORONIC ACID;3-FLUORO PHENYLBORIC ACID;3-FLUOROPHENYLBORNIC ACID;3-FLUOROPHENYLBORONIC ACID;RARECHEM AH PB 0217;M-FLUOROPHENYLBORONIC ACID;3-FLUOROBENZENEBORONIC ACID/3-FLUOROPHENYLBORONIC ACID
• CAS NO: 768-35-4
• Molecular Formula: C₆H₆BFO₂
• Molecular Weight: 139.92
• EINECS: 476-720-8
• 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;Boronate Ester;Potassium Trifluoroborate
• Mol File: 768-35-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 214-218 °C(lit.)
• Boiling Point: 271.4 °C at 760 mmHg
• Flash Point: 117.9 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.24 g/cm³
• Vapor Pressure: 2.01E-09mmHg at 25°C
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 7.50±0.10(Predicted)
• Water Solubility: 27.1g/L at 20℃
• BRN: 3030632
• CAS DataBase Reference: 3-Fluorophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluorophenylboronic acid(768-35-4)
• EPA Substance Registry System: 3-Fluorophenylboronic acid(768-35-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-37/39-26-36
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 768-35-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 768-35-4 differently. You can refer to the following data:
1. suzuki reaction
2. Recently used to make novel liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls by palladium-catalyzed cross-couplings also used in the synthesis of o-phenylphenols as potent leukotriene B4 receptor agonists.
3. Intermediates of Liquid Crystals

Flammability and Explosibility

Notclassified

InChI:InChI=1/C26H4F20P2/c27-3-7(31)15(39)23(16(40)8(3)32)47(24-17(41)9(33)4(28)10(34)18(24)42)1-2-48(25-19(43)11(35)5(29)12(36)20(25)44)26-21(45)13(37)6(30)14(38)22(26)46/h1-2H2

Synthetic route

3-chlorofluorobenzene (625-98-9) → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
	95%

3-fluorobromobenzene (1073-06-9) → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
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;

tetrahydroxydiboron (13675-18-8) + 3-fluorobromobenzene (1073-06-9) → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
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.

Triisopropyl borate (5419-55-6) + 1-halo-3-fluorobenzene → 3-fluorophenylboronic acid (768-35-4)

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

meta-fluoroaniline (372-19-0) + tetrahydroxydiboron (13675-18-8) → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
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%

Triisopropyl borate (5419-55-6) + 3-fluorobromobenzene (1073-06-9) → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
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%

tetrahydroxydiboron (13675-18-8) + 3-fluorobenzenediazonium tetrafluoroborate (1996-38-9) → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.25h;	59%

boric acid tributyl ester (688-74-4) + 3-fluoro-phenyl magnesium bromide → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
With diethyl ether und anschliessenden Hydrolyse;

Trimethyl borate (121-43-7) + 3-fluorobromobenzene (1073-06-9) → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
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;

boric acid tributyl ester (688-74-4) + bromo(3-fluorophenyl)magnesium (17318-03-5) → 3-fluorophenylboronic acid (768-35-4)

C8H10BFO2 → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
With hydrogenchloride In water at 20℃; Inert atmosphere; Schlenk technique;

meta-fluoroaniline (372-19-0) → 3-fluorophenylboronic acid (768-35-4)

Conditions	Yield
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

Triisopropyl borate (5419-55-6) + C11H13FO2Zn → 3-fluorophenylboronic acid (768-35-4)

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

3-fluorophenylboronic acid (768-35-4) + 2',3',5'-tris-O-(tert-butyldimethylsilyl)-2'-deoxyinosine (110526-62-0) → N1-(3-fluorophenyl)-2',3',5'-tris-(O-tert-butyldimethylsilyl)-inosine (864847-17-6)

Conditions	Yield
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%

3-fluorophenylboronic acid (768-35-4) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2-(3-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

Conditions	Yield
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;

3-chloro-5-fluoro-benzoic acid (25026-64-6) + 3-fluorophenylboronic acid (768-35-4) → 3-fluoro-5-(3-fluorophenyl)benzoic acid (1214352-53-0)

Conditions	Yield
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%

3-fluorophenylboronic acid (768-35-4) + 4-chloro-3-iodophenol (202982-72-7) → 6-chloro-3'-fluorobiphenyl-3-ol (1354787-35-1)

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

tert-butyl 8-bromo-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (1263795-03-4) + 3-fluorophenylboronic acid (768-35-4) → tert-butyl 8-(3-fluorophenyl)-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (1263795-09-0)

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

5-bromo-2,3-dimethyl-benzoic acid (5613-27-4) + 3-fluorophenylboronic acid (768-35-4) → 5-bromo-2,3-dimethyl-benzoic acid (1427407-47-3)

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

5-bromo-2-methoxy-1,3-dimethylbenzene (14804-38-7) + 3-fluorophenylboronic acid (768-35-4) → C15H15FO

Conditions	Yield
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;

3-fluorophenylboronic acid (768-35-4) + 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	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 130℃; for 0.5h; Microwave irradiation;	100%

2-(4-bromophenyl)-5,6,7-trimethoxy-4H-chromen-4-one (1355483-74-7) + 3-fluorophenylboronic acid (768-35-4) → C24H19FO5

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

2-bromo-4-fluoroaniline (1003-98-1) + 3-fluorophenylboronic acid (768-35-4) → 3',5-difluoro-[1,1'-biphenyl]-2-amine

Conditions	Yield
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;

potassium hydrogenfluoride (1279123-63-5) + 3-fluorophenylboronic acid (768-35-4) → potassium 3-fluorophenyl trifluoroborate

Conditions	Yield
In methanol; water for 0.5h;	100%
In diethyl ether; water at 20℃; for 3h;	99%

7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (1312684-68-6) + 3-fluorophenylboronic acid (768-35-4) → 8-(3-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide

Conditions	Yield
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 + 3-fluorophenylboronic acid (768-35-4) → 5-(3-fluoro-phenyl)-3-[isopropyl-(4-methyl-cyclohexanecarbonyl)-amino]-thiphene-2-carboxylic acid methyl ester

Conditions	Yield
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 + 3-fluorophenylboronic acid (768-35-4) → 5-acetyl-4-[N-(3,5-dichlorophenyl)-N-(3-fluorophenyl)amino]-2-ethyl-6-phenylpyridazin-3(2H)-one

Conditions	Yield
With oxygen; copper diacetate; triethylamine In dichloromethane at 20℃; for 72h; Molecular sieve;	99%

3-fluorophenylboronic acid (768-35-4) + N-(3-tert-butylphenyl)-2-chloronicotinamide (64794-30-5) → N-(3-tert-butylphenyl)-2-(3-fluorophenyl)nicotinamide (1231732-11-8)

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

6-acetyl-4-chloro-2-cyano-3-methylphenyl trifluoromethanesulfonate (1312686-23-9) + 3-fluorophenylboronic acid (768-35-4) → 6-acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile (1312686-24-0)

Conditions	Yield
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 + 3-fluorophenylboronic acid (768-35-4) → C22H23FN2O2

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

N-methylmaleimide (930-88-1) + 3-fluorophenylboronic acid (768-35-4) → (R)-3-(3-fluorophenyl)-1-methyl-2,5-pyrrolidinedione (1314427-25-2)

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

8-bromo-N-(2-(methylsulfonyl)ethyl)-1,6-naphthyridine-2-carboxamide (1611473-65-4) + 3-fluorophenylboronic acid (768-35-4) → 8-(3-fluorophenyl)-N-(2-(methylsulfonyl)ethyl)-1,6-naphthyridine-2-carboxamide (1611473-13-2)

Conditions	Yield
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 + 3-fluorophenylboronic acid (768-35-4) → 3-amino-N-[6-(3-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide

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

3-fluorophenylboronic acid (768-35-4) + 5-bromo-3(2H)-benzofuranone (54450-20-3) → 5-(3-fluorophenyl)benzofuran-3(2H)-one

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

2-methylbenzyl carbamate + 3-fluorophenylboronic acid (768-35-4) → C14H13F

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

3-fluorophenylboronic acid (768-35-4) + 4-methoxybenzyl N,N-dimethylcarbamate (84640-24-4) → 1-fluoro-3-(4-methoxybenzyl)benzene

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

3-methylbenzyl N,N-dimethylcarbamate (16605-27-9) + 3-fluorophenylboronic acid (768-35-4) → C14H13F

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

2-bromo-4-methoxypyridine (89488-29-9) + 3-fluorophenylboronic acid (768-35-4) → 2-(3-fluorophenyl)-4-methoxypyridine

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

3-fluorophenylboronic acid (768-35-4) + 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	Yield
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%

3-fluorophenylboronic acid (768-35-4) + 2-benzyl-1,2,6-thiadiazine 1,1-dioxide (717-41-9) → (S)-6-benzyl-3-(3-fluorophenyl)-3,6-dihydro-2H-1,2,6-thiadiazine 1,1-dioxide

Conditions	Yield
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%

3-fluorophenylboronic acid (768-35-4) + 2-chloro-N-phenylquinazolin-4-amine (144511-93-3) → 4-anilino-2-(3-fluorophenyl)quinazoline (1304764-81-5)

Conditions	Yield
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%

3-fluorophenylboronic acid (768-35-4) + C19H17NO3 → C25H22FNO3

Conditions	Yield
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%

1-phenyl-3-(2-pyridyl)propen-1-one (5325-66-6, 20890-12-4, 72491-18-0) + 3-fluorophenylboronic acid (768-35-4) → (S)-3-(3-fluorophenyl)-1-phenyl-3-(pyridin-2-yl)propan-1-one

Conditions	Yield
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%

Upstream product

• 13675-18-8 tetrahydroxydiboron 
• 1073-06-9 3-fluorobromobenzene 
• 5419-55-6 Triisopropyl borate 
• 372-19-0 meta-fluoroaniline 
• 1996-38-9 3-fluorobenzenediazonium tetrafluoroborate 
• 688-74-4 boric acid tributyl ester 
• 17318-03-5 bromo(3-fluorophenyl)magnesium 
• 121-43-7 Trimethyl borate 
• 625-98-9 3-chlorofluorobenzene 

Downstream Products

• 1841-58-3 3′-fluoro-(1,1′-biphenyl)-4-carboxylic acid 
• 485404-42-0 8-(2-fluoro-benzyl)-6-(3-fluoro-phenyl)-2-(4-methoxy-phenyl)-7-methyl-8H-imidazo[1,2-a]pyrimidin-5-one 
• 599202-09-2 2-(3-nitro-4-methoxyphenyl)-5-(3-fluorophenyl)benzoxazole 
• 33342-18-6 5-(3'-fluorophenyl)furan-2-carbaldehyde 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 697746-04-6 7-chloro-4-(3-fluorophenyl)quinoline 
• 718642-08-1 2-(3-fluorophenyl)[1,3,2]dioxaborolane 

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