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412546

Sigma-Aldrich

2-Amino-1-methylbenzimidazole

95%

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About This Item

Empirical Formula (Hill Notation):
C8H9N3
CAS Number:
Molecular Weight:
147.18
MDL number:
UNSPSC Code:
12352100
eCl@ss:
32151902
PubChem Substance ID:
NACRES:
NA.22

assay

95%

SMILES string

Cn1c(N)nc2ccccc12

InChI

1S/C8H9N3/c1-11-7-5-3-2-4-6(7)10-8(11)9/h2-5H,1H3,(H2,9,10)

InChI key

XDFZKQJLNGNJAN-UHFFFAOYSA-N

General description

The carbonyl-scavenging ability of 2-amino-1-methylbenzimidazole has been investigated. Mechanism of Menshutkin reaction between 2-amino-1-methylbenzimidazole and iodomethane has been studied in gas phase and in liquid acetonitrile. It is reported to form adducts with natural allyl, phenethyl, and benzyl isothiocyanates.

Application

2-Amino-1-methylbenzimidazole may be used for the preparation of 2- or 3-carboxy-4H-pyrimido[2,1-b]-benzazol-4-ones and novel functionalized spiropyran′s derivatives of 2H-1,3-benzoxazinone series.

pictograms

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signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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André Melo et al.
The journal of physical chemistry. B, 110(4), 1877-1888 (2006-02-14)
The quaternization reaction between 2-amino-1-methylbenzimidazole and iodomethane was investigated in the gas phase and in liquid acetonitrile. Both experimental and theoretical techniques were used in this study. In the experimental part of this work, accurate second-order rate constants were obtained
J J Wade et al.
Journal of medicinal chemistry, 26(4), 608-611 (1983-04-01)
Reactions of 2-aminobenzothiazole, 2-aminobenzoxazole, and 2-amino-1-methylbenzimidazole with dimethyl aminofumarate (DMAF) or diethyl ethoxymethylenemalonate (DEEM) led to 2- or 3-carboxy-4H-pyrimido[2,1-b]-benzazol-4-ones, respectively. Subsequent derivatization of these carboxylic acids gave the corresponding tetrazolylcarboxamides and tetrazoles. These acidic compounds were tested in the rat
Synthesis and structural characterization of novel 2-benzimidazolylthioureas: adducts of natural isothiocyanates and 2-amino-1-methylbenzimidazole.
Smiechowska A, et al.
Structural Chemistry, 21(5), 955-964 (2010)
Antony O Bulanov et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 71(3), 1146-1152 (2008-06-14)
Six novel functionalized spiropyran's derivatives of 2H-1,3-benzoxazinone series were synthesized by introducing the substituents with chelating ability into 2H-chromene part of the 8'-formyl-7'-hydroxy-3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazine-2-spiro-2'-[2H]-chromene (I) by condensation with 2-aminophenol, 2-amino-4-methylphenol, 2-amino-4-nitrophenol, 2-amino-1-methylbenzimidazole, 4-amino-4H-1,2,4-triazole, N-(4-aminophenyl)acetamide. (1)H NMR, UV/vis, IR spectroscopy combined with
Francisco J Hidalgo et al.
Journal of agricultural and food chemistry, 62(49), 12045-12051 (2014-11-25)
The carbonyl-scavenging ability of 2-amino-1-methylbenzimidazole (AMBI) and the heterocyclic aromatic amine 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was investigated in an attempt to identify new routes that can modify the carbonyl content of foods. The reaction of both AMBI and PhIP with 2-alkenals, 2,4-alkadienals

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