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540633

Sigma-Aldrich

2′-Bromoacetanilide

96%

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About This Item

Linear Formula:
CH3CONHC6H4Br
CAS Number:
Molecular Weight:
214.06
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
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)
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)
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)
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)

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