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

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

Uses

Used in Pharmaceutical Industry:
1,2-Dibromo-4-fluorobenzene is used as an intermediate for the production of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
1,2-Dibromo-4-fluorobenzene is also utilized as an intermediate in the synthesis of agrochemicals, playing a role in the creation of pesticides and other agricultural chemicals to protect crops and enhance yields.
Used in Organic Synthesis:
1,2-Dibromo-4-fluorobenzene is employed as a building block in organic synthesis, enabling the construction of complex organic molecules and compounds with specific properties and applications.
Used in Research and Development:
In the field of pharmaceutical research, 1,2-Dibromo-4-fluorobenzene is used as a key component in the synthesis of biologically active molecules and functional materials, aiding in the discovery and development of innovative treatments and technologies.

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

• 1424360-19-9 1,2-di(2'-methoxyphenyl)-4-fluorobenzene 
• 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 
• 1265682-43-6 1-bromo-4-fluoro-2-trimethylsilylbenzene 
• 1265682-44-7 2-bromo-4-fluoro-1-trimethylsilylbenzene 
• 1265682-42-5 4-fluoro-1,2-bis(trimethylsilyl)benzene 
• 65610-14-2 4-fluorophthalonitrile 
• 112204-57-6 dihydroxy-(5-bromo-2-fluorophenyl)-borane 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

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.