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549606

Sigma-Aldrich

2′-Aminoacetanilide

98%

Synonym(s):

N-(2-Aminophenyl)acetamide, o-Aminoacetanilide

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About This Item

Linear Formula:
CH3CONHC6H4NH2
CAS Number:
34801-09-7
Molecular Weight:
150.18
MDL number:
MFCD00210388
UNSPSC Code:
12352100
PubChem Substance ID:
24874710

Assay

98%

mp

133-137 °C (lit.)

SMILES string

CC(=O)Nc1ccccc1N

InChI

1S/C8H10N2O/c1-6(11)10-8-5-3-2-4-7(8)9/h2-5H,9H2,1H3,(H,10,11)

InChI key

MPXAYYWSDIKNTP-UHFFFAOYSA-N

General description

2′-Aminoacetanilide (2-aminoacetanilide, o-aminoacetanilide) can be prepared by the catalytic hydrogenation of 2-nitroacetanilide using 10%Pd/C (palladium/carbon).

Application

2′-Aminoacetanilide may be used in the preparation of:
  • 2-Methylbenzimidazole.
  • N-(2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)phenyl)-5-methylfuran-2-carboxamide, a potent cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor.
  • Azobenzothiazole dyes, N-[2-(6-nitrobenzothiazol-2-ylazo)phenyl]acetamide and N-[2-(benzothiazol-2-ylazo)phenyl]acetamide.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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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A short synthesis of phenanthro [2, 3-d] imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles.
Fonseca T, et al.
Tetrahedron, 57(9), 1793-1799 (2001)
Novel azobenzothiazole dyes from 2-nitrosobenzothiazoles.
Faustino H, et al.
Dyes and Pigments, 83(1), 88-94 (2009)
Nanomolar potency pyrimido-pyrrolo-quinoxalinedione CFTR inhibitor reduces cyst size in a polycystic kidney disease model.
Tradtrantip L, et al.
Journal of Medicinal Chemistry, 52(20), 6447-6455 (2009)
Cyclization of o-phenylenediamines by CO2 in the presence of H2 for the synthesis of benzimidazoles.
Yu B, et al.
Green Chemistry, 15(1), 95-99 (2013)

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