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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)

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