55617
N-(Hydroxymethyl)benzamide
≥98.0%
Synonym(s):
Benzamidomethanol
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About This Item
Empirical Formula (Hill Notation):
C8H9NO2
CAS Number:
Molecular Weight:
151.16
EC Number:
228-495-0
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
2045129
MDL number:
assay
≥98.0%
mp
95-100 °C
SMILES string
OCNC(=O)c1ccccc1
InChI
1S/C8H9NO2/c10-6-9-8(11)7-4-2-1-3-5-7/h1-5,10H,6H2,(H,9,11)
InChI key
UOUBPDZUBVJZOQ-UHFFFAOYSA-N
Other Notes
Aminomethylating reagent; employed e.g. for preparing α-amino phosphonic acids; Preparation of benzamidomethyl protected prodrugs which are fairly stable in physiological medium
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R J Simmonds et al.
Anti-cancer drug design, 3(2), 91-101 (1988-08-01)
Of the three N-hydroxymethyl compounds in the title, the first two have pronounced antineoplastic activity while the latter is biologically inactive. Crystals of the triazene have monoclinic symmetry with a = 8.540(1), b = 6.346(4), c = 22.460(5)A, beta =
W J Tenn et al.
Organic letters, 3(1), 75-78 (2001-06-30)
[figure: see text] The rate constants for the hydronium ion, hydroxide, and water-catalyzed breakdown of N-(hydroxymethyl)benzamide (1), 4-chloro-N-(hydroxymethyl)benzamide (2), and 2,4-dichloro-N-(hydroxymethyl)benzamide (3) in H2O, at 25 degrees C, I = 1.0 (KCl), have been determined. The reactions of 1, 2
J.J. Getz et al.
The Journal of Organic Chemistry, 57, 1702-1702 (1992)
M. Sting et al.
Synthesis, 132-132 (1990)
D Ross et al.
Life sciences, 32(6), 597-604 (1983-02-07)
N-Formylbenzamide and benzamide were characterised by high pressure liquid chromatography and mass spectrometry as products of the metabolism of N-hydroxymethylbenzamide in incubation mixtures with mouse liver preparations and isolated hepatocytes. This biotransformation occurred predominantly in 9000g and microsomal supernatant fractions
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