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717436

Sigma-Aldrich

Benzamide oxime

97%

Synonym(s):

N-Hydroxybenzamide

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About This Item

Empirical Formula (Hill Notation):
C7H8N2O
CAS Number:
613-92-3
Molecular Weight:
136.15
EC Number:
210-361-8
MDL number:
MFCD00474011
UNSPSC Code:
12352100
PubChem Substance ID:
329763488
NACRES:
NA.22

Assay

97%

form

solid

mp

74-78 °C

SMILES string

N\C(=N\O)c1ccccc1

InChI

1S/C7H8N2O/c8-7(9-10)6-4-2-1-3-5-6/h1-5,10H,(H2,8,9)

InChI key

MXOQNVMDKHLYCZ-UHFFFAOYSA-N

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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A Jousserandot et al.
Biochemistry, 37(49), 17179-17191 (1998-12-23)
Oxidation by rat liver microsomes of 13 compounds involving a C=N(OH) function (including N-hydroxyguanidines, amidoximes, ketoximes, and aldoximes) was found to occur with the release of nitrogen oxides such as NO, NO2-, and NO3-. The greatest activities were observed with
A K Fröhlich et al.
Xenobiotica; the fate of foreign compounds in biological systems, 35(1), 17-25 (2005-03-25)
N-Hydroxyamidines (amidoximes) can act as pro-drugs of amidines (e.g. ximelagatran, a novel direct thrombin inhibitor). This known pro-drug principle is based on the N-reduction of an oral bioavailable amidoxime to its active form. Previous study of the metabolism of the
B Clement et al.
Archiv der Pharmazie, 322(7), 431-435 (1989-07-01)
At pH 7.4 neither benzamidine (1) is ring-hydroxylated nor benzamidoxime (2) is N-hydroxylated, reduced or ring-hydroxylated by aerobic incubations with microsomal fractions (12000 g supernatant, microsomes) of rabbit liver homogenates and NADPH. Products of hydrolytic processes are also not detected.
B Clement et al.
The Journal of biological chemistry, 272(31), 19615-19620 (1997-08-01)
Drugs containing strong basic nitrogen functional groups can be N-oxygenated to genotoxic products. While the reduction of such products is of considerable toxicological significance, most in vitro studies have focused on oxygen-sensitive reductase systems. However, an oxygen-insensitive microsomal hydroxylamine reductase
T L Deegan et al.
Bioorganic & medicinal chemistry letters, 9(2), 209-212 (1999-02-18)
1,2,4-Oxadiazoles have been prepared in parallel using 1,1'-carbonyldiimidazole (CDI) as a reagent for both formation and cyclodehydration of O-acyl benzamidoximes. The use of CDI facilitates parallel purification of the oxadiazole products by simple liquid-liquid extraction and filtration.
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