2369-37-1

Basic information

• Product Name: 1,2-DIBROMO-4-FLUOROBENZENE
• Synonyms: 3,4-DIBROMOFLUOROBENZENE;1,2-DIBROMO-4-FLUOROBENZENE;1,2-Dibromo-4-fluorobenzene,98%;1,2-Dibromo-4-fluorobenzene 99%;1,2-Dibromo-4-fluorobenzene99%;3,4-Dibromo-1-fluorobenzene;1,2-DibroMo-4-fluorobenzene[3,4-DibroMofluorobenzene];1,2-Dibromo-4-fluorobezene
• CAS NO: 2369-37-1
• Molecular Formula: C₆H₃Br₂F
• Molecular Weight: 253.89
• EINECS: 219-131-1
• Product Categories: Bromine Compounds;Fluorine Compounds;Fluorine series
• Mol File: 2369-37-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 69℃
• Boiling Point: 220℃
• Flash Point: 87℃
• Appearance: /
• Density: 2.014
• Refractive Index: 1.5780-1.5820
• CAS DataBase Reference: 1,2-DIBROMO-4-FLUOROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIBROMO-4-FLUOROBENZENE(2369-37-1)
• EPA Substance Registry System: 1,2-DIBROMO-4-FLUOROBENZENE(2369-37-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 2369-37-1(Hazardous Substances Data)

Usage

General Description

1,2-Dibromo-4-fluorobenzene is a chemical compound with the molecular formula C6H3Br2F. It is a colorless, crystalline solid and is classified as a halogenated aromatic compound. 1,2-Dibromo-4-fluorobenzene is used as an intermediate for the production of various pharmaceuticals, agrochemicals, and other organic compounds. It is also used as a building block in the synthesis of biologically active molecules and functional materials. The compound is a halogenated aromatic compound with potential use in organic synthesis and pharmaceutical research. It is important to handle this compound carefully as it is toxic, and may cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C6H3Br2F/c7-5-2-1-4(9)3-6(5)8/h1-3H

Synthetic route

fluorobenzene (462-06-6) → 1,2,-dibromo-4-fluorobenzene (2369-37-1)

Conditions	Yield
With bromine; iron

3,4-dibromoaniline (615-55-4) → 1,2,-dibromo-4-fluorobenzene (2369-37-1)

Conditions	Yield
With hydrogenchloride; tetrafluoroboric acid; sodium nitrite Erhitzen des Reaktionsprodukts auf 160grad;

1-Bromo-4-fluorobenzene (460-00-4) → 1,2,-dibromo-4-fluorobenzene (2369-37-1)

Conditions	Yield
With bromine; iron

4-fluoroaniline (371-40-4) → 1,2,-dibromo-4-fluorobenzene (2369-37-1)

Conditions	Yield
With tert.-butylnitrite; copper(ll) bromide In acetonitrile

bromine (7726-95-6) + 1-Bromo-4-fluorobenzene (460-00-4) + iron-powder → 1,2,-dibromo-4-fluorobenzene (2369-37-1) + 2,4-dibromo-1-fluorobenzene (1435-53-6)

fluorobenzene (462-06-6) + 1-1.3 mol bromine + iron-turnings → 1,2,-dibromo-4-fluorobenzene (2369-37-1) + 2,4-dibromo-1-fluorobenzene (1435-53-6) + 1-Bromo-4-fluorobenzene (460-00-4)

dimethylmonochlorosilane (1066-35-9) + 1,2,-dibromo-4-fluorobenzene (2369-37-1) → 1,2-bis(dimethylsilyl)-4-fluorobenzene

Conditions	Yield
With magnesium; lithium chloride at 20℃; for 4h;	88%

zinc(II) cyanide (557-21-1) + 1,2,-dibromo-4-fluorobenzene (2369-37-1) → 4-fluorophthalonitrile (65610-14-2)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium(0); polymethylhydroxysilane In N,N-dimethyl acetamide at 100℃; for 2h;	87%

O-methylresorcine (150-19-6) + 1,2,-dibromo-4-fluorobenzene (2369-37-1) → 2-fluoro-7-methoxydibenzo[b,d]furan

Conditions	Yield
Stage #1: O-methylresorcine; 1,2,-dibromo-4-fluorobenzene With potassium carbonate; copper(II) oxide In N,N-dimethyl-formamide for 3h; Reflux; Stage #2: With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In N,N-dimethyl-formamide at 130℃; for 12h; Inert atmosphere;	83%

chloro-trimethyl-silane (75-77-4) + 1,2,-dibromo-4-fluorobenzene (2369-37-1) → 1-fluoro-3,4-bis(trimethylsilyl)benzene (1265682-42-5)

Conditions	Yield
With magnesium; lithium chloride at 20℃; for 4h;	81%
With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere;	56%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + 4-methylphenylboronic acid (5720-05-8) → 1,2-di(4'-methylphenyl)-4-fluorobenzene (1424360-18-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane at 90℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	81%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + phenylboronic acid (98-80-6) → 1,2-diphenyl-4-fluorobenzene (1424360-17-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane at 90℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	79%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + 9H-carbazole (86-74-8) → C18H11Br2N

Conditions	Yield
With calcium hydride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 18h;	75%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + 4-methoxyphenylboronic acid (5720-07-0) → 1,2-di(4'-methoxyphenyl)-4-fluorobenzene (1424360-20-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane at 90℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	70%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + 2-Methoxyphenylboronic acid (5720-06-9) → 1,2-di(2'-methoxyphenyl)-4-fluorobenzene (1424360-19-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane at 90℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	70%

1,2,-dibromo-4-fluorobenzene (2369-37-1) → 1,2-dibromo-4-fluoro-3-iodobenzene (1539314-91-4)

Conditions	Yield
Stage #1: 1,2,-dibromo-4-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With iodine In tetrahydrofuran for 0.5h;	70%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + 1-pentanamine (110-58-7) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → N-pentyl-4-fluorophthalimide (351992-10-4)

Conditions	Yield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; catacxium A In toluene at 100℃; for 16h; Sealed tube; Inert atmosphere;	60%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + (2,3-dimethoxyphenyl)boronic acid (40972-86-9) → 1,2-di(2',3'-dimethoxyphenyl)-4-fluorobenzene (1424360-23-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane at 90℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	59%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + 4-Vinylphenylboronic acid (2156-04-9) → 1,2-di(4'-vinylphenyl)-4-fluorobenzene (1424360-22-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane at 90℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	48%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + aniline (62-53-3) → 4-fluoro-N1,N2-diphenyl-benzene-1,2-diamine

Conditions	Yield
With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 14h;	32%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + 2,6-dimethylaniline (87-62-7) → N1,N2-bis-(2,6-dimethyl-phenyl)-4-fluoro-benzene-1,2-diamine

Conditions	Yield
With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 14h;	30%

1,2,-dibromo-4-fluorobenzene (2369-37-1) + 2,6-diisopropylbenzenamine (24544-04-5) → N1,N2-bis-(2,6-diisopropyl-phenyl)-4-fluoro-benzene-1,2-diamine

Conditions	Yield
With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 14h;	25%

Trimethyl borate (121-43-7) + 1,2,-dibromo-4-fluorobenzene (2369-37-1) + 2,4-dibromo-1-fluorobenzene (1435-53-6) → dihydroxy-(5-bromo-2-fluorophenyl)-borane (112204-57-6)

Conditions	Yield
With magnesium In tetrahydrofuran; tetrachloromethane; diethyl ether; water; acetic acid

chloro-trimethyl-silane (75-77-4) + 1,2,-dibromo-4-fluorobenzene (2369-37-1) → 1-bromo-4-fluoro-2-trimethylsilylbenzene (1265682-43-6) + 2-bromo-4-fluoro-1-trimethylsilylbenzene (1265682-44-7) + 1-fluoro-3,4-bis(trimethylsilyl)benzene (1265682-42-5)

Conditions	Yield
With Rieke-magnesium (MgR) In tetrahydrofuran at 20 - 40℃; for 1.25h; Inert atmosphere;

1,2,-dibromo-4-fluorobenzene (2369-37-1) → C18H23N3OSi (1607434-42-3)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 0.5 h 2.1: diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 0.17 h / Sealed tube; Sonication 2.2: 40 h / 40 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 26.16 h / 100 °C / Sealed tube; Sonication 4.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 0.33 h / 140 °C / Sealed tube; Microwave irradiation View Scheme

1,2,-dibromo-4-fluorobenzene (2369-37-1) → C19H25N3OSi

Conditions

Yield

Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 0.5 h 2.1: diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 0.17 h / Sealed tube; Sonication 2.2: 40 h / 40 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 26.16 h / 100 °C / Sealed tube; Sonication 4.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 18 h / 20 °C / Sealed tube; Inert atmosphere 4.2: 30 h / 60 °C View Scheme

1,2,-dibromo-4-fluorobenzene (2369-37-1) → ((2,3-dibromo-6-fluorophenyl)ethynyl)trimethylsilane (1539314-93-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 0.5 h 2.1: diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 0.17 h / Sealed tube; Sonication 2.2: 40 h / 40 °C View Scheme

1,2,-dibromo-4-fluorobenzene (2369-37-1) → 4-fluoro-3-((trimethylsilyl)ethynyl)phthalonitrile (1539314-94-7)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 0.5 h 2.1: diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 0.17 h / Sealed tube; Sonication 2.2: 40 h / 40 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 26.16 h / 100 °C / Sealed tube; Sonication View Scheme

1,2,-dibromo-4-fluorobenzene (2369-37-1) → (S)-1-(3-hydroxy-3-methylbutan-2-yl)-1H-indole-4,5-dicarbonitrile (1539314-32-3)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C 1.2: 0.5 h 2.1: diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 0.17 h / Sealed tube; Sonication 2.2: 40 h / 40 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl acetamide / 26.16 h / 100 °C / Sealed tube; Sonication 4.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 0.5 h / 60 °C / Sealed tube; Inert atmosphere 4.2: 0.25 h / 140 °C / Microwave irradiation View Scheme

Upstream product

• 462-06-6 fluorobenzene 
• 7726-95-6 bromine 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 371-40-4 4-fluoroaniline 
• 615-55-4 3,4-dibromoaniline 

Downstream Products

• 1265682-42-5 4-fluoro-1,2-bis(trimethylsilyl)benzene 
• 1265682-43-6 1-bromo-4-fluoro-2-trimethylsilylbenzene 
• 1265682-44-7 2-bromo-4-fluoro-1-trimethylsilylbenzene 
• 1539314-98-1 3-ethynyl-4-fluorophthalonitrile 
• 1539314-52-7 (R)-1-(1-(3-cyanophenyl)ethyl)-1H-indole-4,5-dicarbonitrile 
• 1539314-50-5 (R)-1-(1-phenylethyl)-1H-indole-4,5-dicarbonitrile 
• 1539314-94-7 4-fluoro-3-((trimethylsilyl)ethynyl)phthalonitrile 
• 1539314-93-6 ((2,3-dibromo-6-fluorophenyl)ethynyl)trimethylsilane 
• 1539314-91-4 1,2-dibromo-4-fluoro-3-iodobenzene 
• 1607434-42-3 C₁₈H₂₃N₃OSi 
• 1424360-19-9 1,2-di(2'-methoxyphenyl)-4-fluorobenzene 
• 65610-14-2 4-fluorophthalonitrile 
• 112204-57-6 dihydroxy-(5-bromo-2-fluorophenyl)-borane 

Relevant articles and documents

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Preparation process of fluorine substituted aromatic compound

A preparation process of a fluorine substituted aromatic compound comprising reacting an alkali metal or alkali earth metal salt of an aromatic compound having a hydroxy group with an organic fluorinating agent is disclosed. As a representative fluorinating agent, a bis-dialkylamino-difluoromethane compound, for example, 2,2′-difluoro-1,3-dimethylimidazolidine, is exemplified. According to the process, an industrially useful fluorinated aromatic compound, for example, a fluorobenzene, a fluorine substituted benzophenone, a fluorine substituted diarylsulfone can be prepared with ease in economy without specific equipment.