Description

4-Chloro-3-(trifluoromethyl)benzyl bromide (CAS No. 261763-23-9) is a high-purity halogenated aromatic compound with the molecular formula C₈H₅BrClF₃. This organobromine reagent is a versatile building block in synthetic organic chemistry, particularly for nucleophilic substitution reactions and cross-coupling methodologies. The presence of both bromomethyl and chloro substituents on the benzene ring, along with the electron-withdrawing trifluoromethyl group, makes it an excellent electrophile for C-C bond formation. Supplied as a clear to pale yellow liquid (or low-melting solid depending on storage conditions), it is moisture-sensitive and should be handled under inert atmosphere. Ideal for pharmaceutical intermediates, agrochemical synthesis, and material science applications requiring selective functionalization. Purity is typically ≥95% by GC or HPLC analysis. Store at 2-8°C in amber glass under argon.

Properties

• CAS Number: 261763-23-9
• Complexity: 171
• IUPAC Name: 4-(bromomethyl)-1-chloro-2-(trifluoromethyl)benzene
• InChI: InChI=1S/C8H5BrClF3/c9-4-5-1-2-7(10)6(3-5)8(11,12)13/h1-3H,4H2
• InChI Key: LZLIPLUATRVXSB-UHFFFAOYSA-N
• Exact Mass: 271.92152
• Molecular Formula: C8H5BrClF3
• Molecular Weight: 273.48
• SMILES: C1=CC(=C(C=C1CBr)C(F)(F)F)Cl
• Monoisotopic Mass: 271.92152
• Synonyms: 261763-23-9, 4-Chloro-3-(trifluoromethyl)benzyl bromide, DTXSID70380780, DTXCID40331805, 4-(bromomethyl)-1-chloro-2-(trifluoromethyl)benzene, Benzene, 4-(bromomethyl)-1-chloro-2-(trifluoromethyl)-, MFCD01631540, 4-bromomethyl-1-chloro-2-trifluoromethyl-benzene, SCHEMBL120051, CK2018, SBB070920, AKOS015849946, 3-trifluoromethyl-4-chlorobenzylbromide, AC-4170, PS-9949, 3-trifluromethyl-4-chlorobenzyl bromide, 4-chloro-3-trifluoromethylbenzyl bromide, SY074541, 1-bromomethyl-4-chloro-3-trifluoromethyl-benzene, EN300-1929781, 4-CHLORO-3-(TRIFLUOROMETHYL)BENZYL BROMID

Application

This compound serves as a key intermediate in Suzuki-Miyaura and other palladium-catalyzed cross-coupling reactions for biaryl synthesis. The bromomethyl group readily participates in nucleophilic substitutions to create benzyl ethers, amines, or thioethers in medicinal chemistry applications. Its electron-deficient aromatic system makes it valuable for constructing liquid crystal materials and OLED precursors. Researchers also utilize it in the development of CF₃-containing bioactive molecules for drug discovery programs.

Safety and Hazards

GHS Hazard Statements

• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1B (100%)

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