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183695

Sigma-Aldrich

2′-Bromoacetophenone

99%

Synonym(s):

1-Acetyl-2-bromobenzene

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About This Item

Linear Formula:
BrC6H4COCH3
CAS Number:
2142-69-0
Molecular Weight:
199.04
Beilstein:
1931534
EC Number:
218-398-1
MDL number:
MFCD00000067
UNSPSC Code:
12352100
PubChem Substance ID:
24851070
NACRES:
NA.22

Assay

99%

form

liquid

refractive index

n20/D 1.568 (lit.)

density

1.476 g/mL at 25 °C (lit.)

functional group

bromo
ketone

SMILES string

CC(=O)c1ccccc1Br

InChI

1S/C8H7BrO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,1H3

InChI key

PIMNFNXBTGPCIL-UHFFFAOYSA-N

General description

2′-Bromoacetophenone (2-Bromoacetophenone) undergoes enantioselective addition reaction with phenylacetylene catalyzed by chiral camphorsulfonamide. It reacts with aliphatic primary amines in the presence of palladium catalyst to afford 3-methyleneisoindolin-1-ones.

Application

2′-Bromoacetophenone (2-Bromoacetophenone) was used in the synthesis of novel series of non-condensed 5,5-bicycles.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL1188
STBG9398
STBF3271V
STBD8584V
STBD7012V

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Palladium-catalysed convenient synthesis of 3-methyleneisoindolin-1-ones.
Cho CS, et al.
Synthetic Communications, 32(!2), 1821-1827 (2002)
Non-Condensed Trifluoromethylated 5, 5-Bicycles: Synthesis of 2-[3-Alkyl (phenyl)-1H-pyrazol-1-yl]-4-phenyl-5-alkylthiazole and-4, 5, 6, 7-tetrahydrobenzothiazole Systems.
Bonacorso HG, et al.
Synthesis, 2002(08), 1079-1083 (3003)
Enantioselective alkynylation of aromatic ketones catalyzed by chiral camphorsulfonamide ligands.
Gui Lu et al.
Angewandte Chemie (International ed. in English), 42(41), 5057-5058 (2003-11-05)

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