348-57-2

Basic information

• Product Name: 1-Bromo-2,4-difluorobenzene
• Synonyms: 2,4-Difluoro-1-bromobenzene;Bromo-2,4-difluorobenzene;1-BROMO-2,4-DIFLUOROBENZENE;2,4-DIFLUOROBROMOBENZENE;1-Bromo-2,4-difluorobenzene, 98+%;2,4-Difluoro;1-Bromo-2,4-difluorobenzene,min.98%;Benzene, 1-bromo-2,4-difluoro-
• CAS NO: 348-57-2
• Molecular Formula: C₆H₃BrF₂
• Molecular Weight: 192.99
• EINECS: 206-479-4
• Product Categories: Other fluorin-contained compounds;Aromatic Hydrocarbons (substituted) & Derivatives;Miscellaneous;Bromine Compounds;Fluorine Compounds;Aryl;C6;Halogenated Hydrocarbons
• Mol File: 348-57-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: −4 °C(lit.)
• Boiling Point: 145-146 °C(lit.)
• Flash Point: 125 °F
• Appearance: Clear colorless to brown/Liquid
• Density: 1.708 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.94mmHg at 25°C
• Refractive Index: n20/D 1.505(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: INSOLUBLE
• BRN: 1680892
• CAS DataBase Reference: 1-Bromo-2,4-difluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-2,4-difluorobenzene(348-57-2)
• EPA Substance Registry System: 1-Bromo-2,4-difluorobenzene(348-57-2)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39-37/39-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 348-57-2(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to brown liqui

Uses

1-Bromo-2,4-difluorobenzene has been used in:preparation of (2S)-1-(2,4-difluorophenyl)-2-(1,1-dimethyl-1-sila-ethoxy)-propan-1-oneenantiomeric preparation of the key intermediate of chiral azole antifungal agents by a chemoenzymatic process

General Description

1-Bromo-2,4-difluorobenzene undergoes lithiation exclusively at the position having two adjacent halogen substituents, to yield 6-bromo-2,3-difluorobenzoic acid.

InChI:InChI=1/C6H3Cl2F/c7-4-1-2-5(8)6(9)3-4/h1-3H

Upstream product

• 372-18-9 1,3-Difluorobenzene 
• 148854-10-8 (2,4-difluorophenyl)trimethylsilane 
• 64248-56-2 1-bromo-2,6-difluorobenzene 
• 71-43-2 benzene 
• 75-05-8 acetonitrile 

Downstream Products

• 345-24-4 5-bromo-2,4-difluoronitrobenzene 
• 173276-82-9 6-fluoro-1,4-epoxy-1,4-dihydronaphthalene 
• 51788-81-9 2-(2,4-difluorophenyl)propan-2-ol 
• 372-18-9 1,3-Difluorobenzene 
• 590-17-0 cyanomethyl bromide 
• 306308-00-9 P,P'-(1,2-ethanediyl)bis[bis(2,4-difluorophenyl)phosphane] 
• 173837-45-1 1,3-diacetoxy-2-(2,4-difluorophenyl)-2-propanol 
• 173837-46-2 1,3-dipropionyloxy-2-(2,4-difluorophenyl)-2-propanol 
• 173837-48-4 1,3-di-n-butyryloxy-2-(2,4-difluorophenyl)-2-propanol 
• 173837-49-5 1,3-diisobutyryloxy-2-(2,4-difluorophenyl)-2-propanol 
• 173837-47-3 2-(2,4-difluorophenyl)-1,3-di-n-pentanoyloxy-2-propanol 
• 743449-15-2 (2S)-1-(2,4-difluorophenyl)-2-(1,1-dimethyl-1-silaethoxy)-propan-1-one 
• 3939-09-1 2,4-difluorobenzonitrile 
• 288101-48-4 2-(2,4-difluorophenyl)-4,4, 5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Bromination of aromatic compounds using an Fe2O 3/zeolite catalyst

The catalytic bromination of non-activated aromatic compounds has been achieved using an Fe2O3/zeolite catalyst system. FeBr 3 was identified as the catalytic species, formed in situ from HBr and Fe2O3. The catalyst was easy-to-handle and cost effective and could also be recycled. The reaction system was also amenable to the one-pot sequential bromination/C-C bond formation of benzene.

Chemoselective bromodeboronation of organotrifluoroborates using tetrabutylammonium tribromide: Application in (Z)-dibromoalkene syntheses

(Chemical Equation Presented) Tetrabutylammonlum trlbromlde (TBATB) has been found to be a unique bromodeboronatlon reagent for organotrlf luoroborates. When compared to previously reported bromodeboronatlon methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High reglo- and chemoselectlvlty are observed In the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dlbromoalkenes from terminal alkynes has been developed using the TBATB-medlated bromodeboronatlon as a key step.

Exploring Structural Opportunities: The Regioflexible Substitution of 1,3-Difluorobenzene

To demonstrate the superiority of modern organometallic methods, the inexpensive starting material 1,3-difluorobenzene has been selectively converted into the three benzoic acids and all seven bromobenzoic acids containing the two fluorine atoms in homovicinal positions. The 2,6-difluorobenzoic acid (1) was prepared in a one-pot reaction consisting of direct metallation and carboxylation. The key step on the route to the bromobenzoic acid 4 was a deprotonation-triggered bromine migration from the 2- to the 4-position. All other products were attained through (2,6-difluorophenyl)triethylsilane (11). Consecutive deprotonation of the sites adjacent to the fluorine atoms, followed by appropriate electrophilic substitution, provided not only the acid 7 but also the dibromo and iodobromo derivatives 13 and 23. These in turn gave the isomers 14 and 24 upon base-mediated migration of the heaviest halogen, which made the acids 8 and 10 directly accessible. The regiocontrolled monodebromination of intermediate 14 afforded (4-bromo-2,6-difluoro)triethylsilane (15), which opened the route to the acids 3 and 5 (by carboxylation and protodesilylation) and to acid 9 (by carboxylation and bromodesilylation). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.