Description

2-(Bromomethyl)-1,4-difluorobenzene (CAS No. 85117-99-3) is a high-purity aromatic compound with the molecular formula C₇H₅BrF₂. This organobromine reagent features a bromomethyl group at the 2-position and fluorine atoms at the 1- and 4-positions of the benzene ring, making it a versatile building block for synthetic organic chemistry. The compound is supplied as a clear to pale yellow liquid with >98% purity (GC), stabilized for extended shelf life under recommended storage conditions (2-8°C, inert atmosphere). Its unique structure enables selective functionalization in pharmaceutical intermediates, agrochemicals, and materials science applications. Special handling precautions are required due to moisture sensitivity and lachrymatory properties.

Properties

• CAS Number: 85117-99-3
• Complexity: 108
• IUPAC Name: 2-(bromomethyl)-1,4-difluoro-benzene
• InChI: InChI=1S/C7H5BrF2/c8-4-5-3-6(9)1-2-7(5)10/h1-3H,4H2
• InChI Key: ONWGSWNHQZYCFK-UHFFFAOYSA-N
• Exact Mass: 205.95427
• Molecular Formula: C7H5BrF2
• Molecular Weight: 207.01
• SMILES: C1=CC(=C(C=C1F)CBr)F
• Monoisotopic Mass: 205.95427
• Synonyms: 2,5-Difluorobenzyl bromide, 85117-99-3, 2-(Bromomethyl)-1,4-difluorobenzene, Benzene, 2-(bromomethyl)-1,4-difluoro-, EINECS 285-651-0, ONWGSWNHQZYCFK-UHFFFAOYSA-, DTXSID50234237, DTXCID50156728, 285-651-0, inchi=1/c7h5brf2/c8-4-5-3-6(9)1-2-7(5)10/h1-3h,4h2, 2,5-difluorobenzylbromide, alpha-Bromo-2,5-difluorotoluene, MFCD00009897, 2,5-difluoro-benzylbromide, a-bromo-2,5-difluorotoluene, SCHEMBL119218, 2-bromomethyl-1,4-difluorobenzene, 2,5-Difluorobenzyl bromide, 98%, 1-bromomethyl-2,5-difluoro-benzene, 2-bromomethyl-1,4-difluoro-benzene, AC-337, SBB006680, AKOS005259229, JS-4100, 2-(Bromomethyl)-1,4-difluorobenzene #, DB-024268, D2597, NS00065098, ST51040004, EN300-102561, F2190-0298, Alpha-Bromo-2,5-difluorotoluene;2-(Bromomethyl)-1,4-difluorobenzene

Application

This compound serves as a key electrophile in nucleophilic substitution reactions for introducing difluorobenzyl moieties. Researchers utilize it in Suzuki-Miyaura cross-coupling reactions to create biaryl structures common in drug discovery. The bromomethyl group readily participates in alkylation reactions to form ethers or amines, while the difluoro substitution pattern influences electronic properties in material science applications. It’s particularly valuable for synthesizing fluorinated liquid crystals and pharmaceutical intermediates requiring controlled lipophilicity.

Safety and Hazards

GHS Hazard Statements

• H225 (87.2%): Highly Flammable liquid and vapor [Danger Flammable liquids]
• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 2 (87.2%)
• Skin Corr. 1B (100%)

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