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540633

Sigma-Aldrich

2′-Bromoacetanilide

96%

Linear Formula:
CH3CONHC6H4Br
CAS Number:
Molecular Weight:
214.06
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

mp

96.5-100.5 °C (lit.)

SMILES string

CC(=O)Nc1ccccc1Br

InChI

1S/C8H8BrNO/c1-6(11)10-8-5-3-2-4-7(8)9/h2-5H,1H3,(H,10,11)

InChI key

VOBKUOHHOWQHFZ-UHFFFAOYSA-N

General description

2′-Bromoacetanilide can be prepared from aniline via bromoacetylation. 2-Bromoacetanilide undergoes bromination in the presence of acetic acid to afford 2,4′-dibromoacetanilide.

Application

2′-Bromoacetanilide (2-bromoacetanilide) may be used to synthesize:
  • 2-iodophenylmethylphosphinic acid
  • substituted biaryl acetamide compounds
  • benzisoxazolo[2,3-a]pyridinium tetrafluoroborates

Packaging

25 g in glass bottle

Certificate of Analysis

Certificate of Origin

W C Peter Tsang et al.
The Journal of organic chemistry, 73(19), 7603-7610 (2008-09-03)
The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the...
Extension of the Smiles rearrangement. Displacement of an aromatic amide group by an amine nitrogen.
Gilman NW, et al.
The Journal of Organic Chemistry, 38(2), 373-377 (1973)
Palladium-catalyzed direct arylation of pyridine N-oxide with 2-bromoacetanilides. Synthesis of benzisoxazolo [2, 3-a] pyridinium tetrafluoroborates.
Myers JT and Hanna JM.
Tetrahedron Letters, 53(2), 612-615 (2012)
Synthesis of chelating compounds to be used as potential bone seekers.
G Shtacher et al.
Journal of medicinal chemistry, 9(2), 197-203 (1966-03-01)
Synthesis and molecular structure of 1, 3-dihydro-1-hydroxy-3-methyl-1, 2, 3-benziodoxaphosphole 3-oxide.
Balthazor TM, et al.
The Journal of Organic Chemistry, 43(23), 4538-4540 (2978)

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