CAS 370104-05-5

1-[3-(Bromomethyl)phenyl]-2,2,2-trifluoroethanone

Description:

1-[3-(Bromomethyl)phenyl]-2,2,2-trifluoroethanone is an organic compound characterized by its unique structure, which includes a bromomethyl group attached to a phenyl ring and a trifluoroethanone moiety. This compound features a trifluoromethyl group, which imparts significant electronegativity and lipophilicity, influencing its reactivity and solubility in organic solvents. The presence of the bromomethyl group enhances its potential for nucleophilic substitution reactions, making it a valuable intermediate in organic synthesis. Additionally, the trifluoroethanone functional group contributes to its reactivity, particularly in electrophilic reactions. The compound is likely to exhibit moderate stability under standard conditions but may be sensitive to moisture and light. Its applications may span various fields, including pharmaceuticals and agrochemicals, where it can serve as a building block for more complex molecules. Safety precautions should be observed when handling this compound due to the presence of bromine and fluorine, which can pose health and environmental risks.

Formula: C₉H₆BrF₃O

InChI: InChI=1S/C9H6BrF3O/c10-5-6-2-1-3-7(4-6)8(14)9(11,12)13/h1-4H,5H2

InChI key: InChIKey=PJBFZGACRBKRKV-UHFFFAOYSA-N

SMILES: C(C(F)(F)F)(=O)C1=CC(CBr)=CC=C1

Synonyms:

• 1-[3-(Bromomethyl)phenyl]-2,2,2-trifluoroethanone
• 3-Trifluoroacetylbenzyl bromide
• Ethanone, 1-[3-(bromomethyl)phenyl]-2,2,2-trifluoro-

1-[3-(Bromomethyl)phenyl]-2,2,2-trifluoroethan-1-one

CAS: 370104-05-5

1-[3-(Bromomethyl)phenyl]-2,2,2-trifluoroethan-1-one is a potent and selective inhibitor of acetylcholinesterase, with nanomolar range of inhibition. The crystal structure of 1-[3-(Bromomethyl)phenyl]-2,2,2-trifluoroethan-1-one has been determined. It is a white crystalline solid that is soluble in water. This compound has validated activity against acetylcholinesterase and molecular modeling studies have been conducted to elucidate the mode of binding to the active site. The postulated mechanism for inhibition includes complexation with an enzyme moiety (a serine residue) and the formation of a covalent bond with an electrophilic center on the enzyme that can be attacked by a nucleophile on the inhibitor molecule.

Formula: C₉H₆BrF₃O

Purity: Min. 95%

Molecular weight: 267.04 g/mol

Ref: 3D-VPA10405