156682-53-0

Basic information

• Product Name: 3-Bromo-2-fluoro-phenol
• Synonyms: 3-Bromo-2-fluoro-phenol;3-Bromo-2-fluorophenol98%
• CAS NO: 156682-53-0
• Molecular Formula: C₆H₄BrFO
• Molecular Weight: 190.9977632
• Mol File: 156682-53-0.mol

Chemical Properties

• Boiling Point: 207.4 °C at 760 mmHg
• Flash Point: 79.2 °C
• Appearance: /
• Density: 1.764 g/cm³
• Vapor Pressure: 0.157mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.74±0.10(Predicted)
• CAS DataBase Reference: 3-Bromo-2-fluoro-phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-2-fluoro-phenol(156682-53-0)
• EPA Substance Registry System: 3-Bromo-2-fluoro-phenol(156682-53-0)

Safety Data

• Hazard Codes: T,Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 156682-53-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-2-fluoro-phenol is used as a key building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications. Its unique structure allows for the creation of diverse medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Bromo-2-fluoro-phenol serves as a fundamental component in the synthesis of pesticides and other crop protection agents, enhancing agricultural productivity and crop protection.
Used in Specialty Chemicals Manufacturing:
3-Bromo-2-fluoro-phenol is utilized as an intermediate in the production of specialty chemicals, which are often used in specific applications such as coatings, adhesives, and other industrial materials.
Organic Synthesis:
3-Bromo-2-fluoro-phenol is also employed as an intermediate in organic synthesis, where it can be further modified to produce a range of organic compounds for various applications.
Safety Considerations:
Due to its reactivity, 3-Bromo-2-fluoro-phenol requires careful handling and storage to prevent potential hazards. It is essential to adhere to proper safety protocols when working with this chemical to ensure the safety of personnel and the integrity of the compound.

InChI:InChI=1/C6H4BrFO/c7-4-2-1-3-5(9)6(4)8/h1-3,9H

Synthetic route

1-bromo-2,3-difluorobenzene (38573-88-5) → 3-bromo-2-fluoro-phenol (156682-53-0) + 2-bromo-6-fluorophenol (2040-89-3)

Conditions	Yield
Stage #1: 1-bromo-2,3-difluorobenzene With potassium trimethylsilonate In diethylene glycol dimethyl ether at 120℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In diethylene glycol dimethyl ether; water at 20℃; Inert atmosphere;

3-bromo-2-fluoro-phenol (156682-53-0) + benzyl bromide (100-39-0) → 1-(benzyloxy)-3-bromo-2-fluorobenzene (295376-29-3)

Conditions	Yield
With potassium carbonate In acetone for 4h; Reflux;	97%

3-bromo-2-fluoro-phenol (156682-53-0) + 6-(benzyloxy)-4-chloro-7-methoxyquinazoline (286371-65-1) → 6-benzyloxy-4-(3-bromo-2-fluorophenoxy)-7-methoxyquinazoline

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1h;	96%

3-bromo-2-fluoro-phenol (156682-53-0) + isopropyl bromide (75-26-3) → 1-bromo-2-fluoro-3-isopropoxybenzene (1160293-59-3)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 14h; Inert atmosphere;	92%

3-bromo-2-fluoro-phenol (156682-53-0) + cyclohexylmethyl alcohol (100-49-2) → 1-bromo-3-(cyclohexylmethoxy)-2-fluorobenzene

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h;	83%

3-bromo-2-fluoro-phenol (156682-53-0) + 6,7-dibenzyloxy-4-chloroquinazoline → 6,7-dibenzyloxy-4-(3-bromo-2-fluorophenoxy)quinazoline

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h;	82%

3-bromo-2-fluoro-phenol (156682-53-0) + benzyl (3S)-3-((4-(2-fluoro-3-pyridyl)pyrimidin-2-yl)amino)piperidine-1-carboxylate → benzyl (3S)-3-((4-(2-(3-bromo-2-fluoro-phenoxy)-3-pyridyl)pyrimidin-2-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 110℃; for 1h;	76.8%

3-bromo-2-fluoro-phenol (156682-53-0) + diphenyliodonium tetrafluoroborate → 1-bromo-2-fluoro-3-phenoxybenzene

Conditions	Yield
Stage #1: 3-bromo-2-fluoro-phenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: diphenyliodonium tetrafluoroborate In tetrahydrofuran at 40℃; for 1h;	76%
Stage #1: 3-bromo-2-fluoro-phenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: diphenyliodonium tetrafluoroborate In tetrahydrofuran at 40℃; for 1h;	76%

3-bromo-2-fluoro-phenol (156682-53-0) + bis(3-fluorophenyl)iodonium tetrafluoroborate (1426251-76-4) → 1-bromo-2-fluoro-3-(3-fluorophenoxy)benzene

Conditions	Yield
Stage #1: 3-bromo-2-fluoro-phenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: bis(3-fluorophenyl)iodonium tetrafluoroborate In tetrahydrofuran at 40℃; for 1h;	71%
Stage #1: 3-bromo-2-fluoro-phenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: bis(3-fluorophenyl)iodonium tetrafluoroborate In tetrahydrofuran at 40℃; for 1h;	71%

3-bromo-2-fluoro-phenol (156682-53-0) + 2-methyl-3-bromo-1-propene (1458-98-6) → C10H10BrFO

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Inert atmosphere; Reflux;	70%

3-bromo-2-fluoro-phenol (156682-53-0) + sodium chlorodifluoroacetate (1895-39-2) → 1-bromo-3-(difluoromethoxy)-2-fluorobenzene (1242249-28-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;	47%
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;

4-bromotetrahydro-2H-pyran (25637-16-5) + 3-bromo-2-fluoro-phenol (156682-53-0) → C11H12BrFO2

Conditions	Yield
With caesium carbonate In acetonitrile at 80℃; for 18h;	31.24%

3-bromo-2-fluoro-phenol (156682-53-0) + (3-(aminocarbonyl)phenyl)boronic acid → 3-(2-fluoro-3-hydroxy-phenyl)benzamide

Conditions	Yield
With potassium phosphate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride In 1,4-dioxane; ethanol at 100℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube;	29%

3-bromo-2-fluoro-phenol (156682-53-0) + phenylboronic acid (98-80-6) → 1-bromo-2-fluoro-3-phenoxybenzene

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane at 20℃; Molecular sieve;	4%

3-bromo-2-fluoro-phenol (156682-53-0) + 1-bromo-hexane (111-25-1) → 6-bromo-2-hexyloxyfluorobenzene (176317-01-4) + 2-Hexyloxy-1,6,7,8-tetrafluorophenanthrene

Conditions	Yield
With hydrogenchloride; potassium carbonate In water; acetone

3-bromo-2-fluoro-phenol (156682-53-0) → 2-(3-(difluoromethoxy)-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1313426-18-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: potassium acetate / 1,4-dioxane / 2 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 110 °C View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → 4-[2-(benzyloxy)-6-bromophenoxymethyl]pyridine (1372147-59-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → 1-benzyl-4-[2-(benzyloxy)-6-bromophenoxymethyl]pyridinium bromide (1372147-65-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C 3.1: acetone / 18 h / Reflux View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → 1-benzyl-4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine (1372147-73-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C 3.1: acetone / 18 h / Reflux 4.1: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate (1372147-81-3)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C 3.1: acetone / 18 h / Reflux 4.1: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C 5.1: potassium hydrogencarbonate / dichloromethane / 24 h / 0 - 20 °C View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → ethyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate (1372147-83-5)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C 3.1: acetone / 18 h / Reflux 4.1: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C 5.1: potassium hydrogencarbonate / 1,2-dichloro-ethane / 2 h / Reflux View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → benzyl 7-(benzyloxy)-2',3'-dihydro-1'H,2H-spiro[1-benzofuran-3,4'-pyridine]-1'-carboxylate (1372147-92-6)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C 3.1: acetone / 18 h / Reflux 4.1: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C 5.1: potassium hydrogencarbonate / dichloromethane / 24 h / 0 - 20 °C 6.1: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); silver carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 140 °C / Inert atmosphere View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → ethyl 7-(benzyloxy)-2',3'-dihydro-1'H,2H-spiro[1-benzofuran-3,4'-pyridine]-1'-carboxylate (1372147-94-8)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C 3.1: acetone / 18 h / Reflux 4.1: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C 5.1: potassium hydrogencarbonate / 1,2-dichloro-ethane / 2 h / Reflux 6.1: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); silver carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 140 °C / Inert atmosphere View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → ethyl 7-hydroxy-2H-spiro[1-benzofuran-3,4'-piperidine]-1'-carboxylate (1372148-02-1)

Conditions

Yield

Multi-step reaction with 7 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C 3.1: acetone / 18 h / Reflux 4.1: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C 5.1: potassium hydrogencarbonate / 1,2-dichloro-ethane / 2 h / Reflux 6.1: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); silver carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 140 °C / Inert atmosphere 7.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 18 h / 20 °C / 760.05 Torr View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → 2H-spiro[1-benzofuran-3,4'-piperidin]-7-ol hydrochloride (1372148-00-9)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: potassium carbonate / acetone / 4 h / Reflux 2.1: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.5 h / 60 °C / Cooling with ice 2.2: 2 h / 100 °C 3.1: acetone / 18 h / Reflux 4.1: sodium tetrahydroborate / methanol / 2 h / -5 - 20 °C 5.1: potassium hydrogencarbonate / 1,2-dichloro-ethane / 2 h / Reflux 6.1: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); silver carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 140 °C / Inert atmosphere 7.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 18 h / 20 °C / 760.05 Torr 8.1: hydrogenchloride; water; acetic acid / 18 h / Reflux View Scheme

tetrahydrofurfuryl bromide (1192-30-9) + 3-bromo-2-fluoro-phenol (156682-53-0) → 2-(3-bromo-2-fluoro-phenoxymethyl)-tetrahydrofuran (1398923-65-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 2h; Inert atmosphere;

3-bromo-2-fluoro-phenol (156682-53-0) → cis-7-[3-(1,1-dioxo-1-thiomorpholin-4-ylmethyl)-cyclobutyl]-5-[2-fluoro-3-(tetrahydro-furan-2-ylmethoxy)-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Conditions

Yield

Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 18 h / 80 °C / Inert atmosphere 3: potassium phosphate; sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1.5 h / 100 °C / Inert atmosphere; sealed tube View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → 2-(4-amino-5-{2-fluoro-3-[(S)-1-(tetrahydro-furan-2-yl)methoxy]-phenyl}-pyrrolo[2,3-d]pyrimidin-7-yl)-5-oxa-7-aza-spiro[3.4]octan-6-one

Conditions

Yield

Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 18 h / 100 °C / Inert atmosphere 3: potassium phosphate; sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1.5 h / 80 °C / Inert atmosphere; sealed tube View Scheme

3-bromo-2-fluoro-phenol (156682-53-0) → 1-{4-[cis-3-(4-amino-5-{2-fluoro-3-[(S)-1-(tetrahydro-furan-2-yl)methoxy]-phenyl}-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-piperazin-1-yl}-ethanone

Conditions

Yield

Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 18 h / 100 °C / Inert atmosphere 3: potassium phosphate; sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 2.5 h / 100 °C / Inert atmosphere; sealed tube View Scheme

Upstream product

• 38573-88-5 1-bromo-2,3-difluorobenzene 

Downstream Products

• 176317-01-4 6-bromo-2-hexyloxyfluorobenzene 
• 1313426-18-4 2-(3-(difluoromethoxy)-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1372147-59-5 4-[2-(benzyloxy)-6-bromophenoxymethyl]pyridine 
• 1372147-65-3 1-benzyl-4-[2-(benzyloxy)-6-bromophenoxymethyl]pyridinium bromide 
• 1372147-73-3 1-benzyl-4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine 
• 1372147-81-3 benzyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate 
• 1372147-83-5 ethyl 4-[2-(benzyloxy)-6-bromophenoxymethyl]-1,2,3,6-tetrahydropyridine-1-carboxylate 
• 1372147-92-6 benzyl 7-(benzyloxy)-2',3'-dihydro-1'H,2H-spiro[1-benzofuran-3,4'-pyridine]-1'-carboxylate 
• 1372147-94-8 ethyl 7-(benzyloxy)-2',3'-dihydro-1'H,2H-spiro[1-benzofuran-3,4'-pyridine]-1'-carboxylate 
• 295376-29-3 1-(benzyloxy)-3-bromo-2-fluorobenzene 
• 1398923-65-3 2-(3-bromo-2-fluoro-phenoxymethyl)-tetrahydrofuran 
• 1398923-63-1 2-[2-fluoro-3-(tetrahydro-furan-2-ylmethoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 1398923-69-7 2-{2-fluoro-3-[(S)-1-(tetrahydro-furan-2-yl)methoxy]-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 1398923-71-1 (S)-2-(3-bromo-2-fluoro-phenoxymethyl)-tetrahydrofuran 

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