352535-97-8

Basic information

• Product Name: 3-BROMO-2-FLUOROPHENYLBORONIC ACID
• Synonyms: 3-BroMo-2-fluorobenzeneboronic acid, 98%;3-Bromo-2-fluorophenylboronic Acid (contains varying amounts of Anhydride)
• CAS NO: 352535-97-8
• Molecular Formula: C₆H₅BBrFO₂
• Molecular Weight: 218.82
• Product Categories: blocks;BoronicAcids;Bromides;Aryl;Boronic Acids;Boronic Acids and Derivatives;Boronic Acids
• Mol File: 352535-97-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 225-227 °C(lit.)
• Boiling Point: 326.6 °C at 760 mmHg
• Flash Point: 151.3 °C
• Appearance: /Solid
• Density: 1.75 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.35±0.58(Predicted)
• CAS DataBase Reference: 3-BROMO-2-FLUOROPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-2-FLUOROPHENYLBORONIC ACID(352535-97-8)
• EPA Substance Registry System: 3-BROMO-2-FLUOROPHENYLBORONIC ACID(352535-97-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 352535-97-8(Hazardous Substances Data)

Usage

Uses

suzuki reaction

InChI:InChI=1S/C6H5BBrFO2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,10-11H

Synthetic route

2-bromo-pyridine (109-04-6) + (3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → 2-(3-bromo-2-fluoro-phenyl)-pyridine (1402215-21-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 100℃; for 1h; Suzuki Coupling; Inert atmosphere;	94%

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) + 2,4-dichloro-6-iodophenol (2040-83-7) → C12H6BrCl2FO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Inert atmosphere; Reflux;	80%

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) + nitrobenzene (98-95-3) → 3-bromo-2-fluoro-N-phenylaniline

Conditions	Yield
Stage #1: nitrobenzene With [2,2]bipyridinyl; [MoO2Cl2(dmf)2] In toluene for 0.0333333h; Stage #2: (3’-bromo-2-fluorophenyl)boronic acid With triphenylphosphine In toluene at 100℃; for 18h;	78%

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) + 2-chloro-4-pyrimidinecarboxamide (22536-66-9) → 2-(3-bromo-2-fluorophenyl)pyrimidine-4-carboxamide

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; cesium fluoride In ethanol; water at 100℃; Microwave irradiation;	48%

N-hydroxy-N-(naphthalen-2-yl)benzamide + (3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → N-(1-(4-bromo-3-fluoro-2-hydroxyphenyl)naphthalen-2-yl)benzamide

Conditions	Yield
With pyridine; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 25℃; for 12h; Molecular sieve;	43%

4-bromo-1-methyl-1H-imidazole (25676-75-9) + (3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → C10H8BrFN2

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 95℃; for 5h; Inert atmosphere;	18.87%

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → trans-N1-(4-(3-bromo-2-fluorophenyl)-5-chloropyridin-2-yl)cyclohexane-1,4-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 85 °C 2: triethylamine / dimethyl sulfoxide / 18 h / 100 °C View Scheme

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → trans-N1-(5-chloro-4-(2-fluoro-3-(3-fluorobenzylamino)phenyl)pyridin-2-yl)cyclohexane-1,4-diamine trifluoroacetate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 85 °C 2: triethylamine / dimethyl sulfoxide / 18 h / 100 °C 3: potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 2 h / 105 °C View Scheme

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) + 2-fluoro-4-iodo-5-chloropyridine (659731-48-3) → 4-(3-bromo-2-fluorophenyl)-5-chloro-2-fluoropyridine (1377698-52-6)

Conditions	Yield
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane at 85℃; for 3h;

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → C12H5BrCl2O

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / Inert atmosphere; Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Reflux View Scheme

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → C18H17BCl2O3

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / Inert atmosphere; Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Reflux 3: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 3 h / Inert atmosphere; Reflux View Scheme

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → C27H15Cl2N3O

Conditions

Yield

Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / Inert atmosphere; Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Reflux 3: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 3 h / Inert atmosphere; Reflux 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 18 h / Inert atmosphere; Reflux View Scheme

(3’-bromo-2-fluorophenyl)boronic acid (352535-97-8) → C51H29N3O3

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / Inert atmosphere; Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Reflux 3: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 3 h / Inert atmosphere; Reflux 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 18 h / Inert atmosphere; Reflux 5: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium phosphate / water / 24 h / Inert atmosphere; Reflux View Scheme

Downstream Products

• 1377698-52-6 4-(3-bromo-2-fluorophenyl)-5-chloro-2-fluoropyridine 
• 1402215-21-7 2-(3-bromo-2-fluoro-phenyl)-pyridine 

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