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422835

Sigma-Aldrich

2-Chloro-N-(hydroxymethyl)acetamide

98%

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About This Item

Formule linéaire :
ClCH2CONHCH2OH
Numéro CAS:
2832-19-1
Poids moléculaire :
123.54
Numéro CE :
220-598-9
Numéro MDL:
MFCD00021961
Code UNSPSC :
12352100
ID de substance PubChem :
24866457
Nomenclature NACRES :
NA.22

Pureté

98%

Pf

100-105 °C (lit.)

Chaîne SMILES 

OCNC(=O)CCl

InChI

1S/C3H6ClNO2/c4-1-3(7)5-2-6/h6H,1-2H2,(H,5,7)

Clé InChI

TXNSZCSYBXHETP-UHFFFAOYSA-N

Catégories apparentées

Description générale

2-Chloro-N-(hydroxymethyl)acetamide (N-methylolchloracetamide) is a N-hydroxymethyl derivative of chloroacetamide. One of the method reported for its synthesis is by the reaction of 2-chloracetamide with formaldehyde. It has been reported to be a formaldehyde releaser and an infrequent sensitizer to formaldehyde contact allergy. Influence of short and prolonged exposure of 2-chloro-N-(hydroxymethyl)acetamide (as formaldehyde donor/releaser) on lymph node responses has been investigated.

Application

2-Chloro-N-(hydroxymethyl)acetamide (N-hydroxymethylchloroacetamide) may be used as a reagent in the synthesis of 1-(aminomethyl)-2-methoxynaphthalene hydrochloride and as a amidomethylating reagent for N,N-dialkylanilines (Tscherniac-Einhorn reaction).

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314

Classification des risques

Eye Dam. 1 - Skin Corr. 1B

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Anton C de Groot et al.
Contact dermatitis, 61(2), 63-85 (2009-08-27)
This is one of series of review articles on formaldehyde and formaldehyde-releasers (others: formaldehyde in cosmetics, in clothes and in metalworking fluids and miscellaneous). Thirty-five chemicals were identified as being formaldehyde-releasers. Although a further seven are listed in the literature
J Ashby et al.
Mutation research, 156(1-2), 19-32 (1985-04-01)
The industrial biocide chloracetamide-N-metholol (CAM) has been shown to be non-mutagenic to 6 strains of Salmonella using both the plate-incorporation and a pre-incubation test protocol. Its biocidal activity is unlikely to have influenced these results since Kathon 886, a more
Allergic contact dermatitis from the preservative N-methylol-chloracetamide.
S Agren et al.
Contact dermatitis, 6(4), 302-303 (1980-06-01)
Anton de Groot et al.
Contact dermatitis, 63(3), 129-139 (2010-06-25)
We have reviewed formaldehyde-releasers used in metalworking fluids (MWFs) in this and a previous part of a two-part article. These biocides do not appear to be frequent or important sensitizers. Even in highly selected patient groups of metalworkers, mean prevalence
J C Bressi et al.
Journal of medicinal chemistry, 44(13), 2080-2093 (2001-06-19)
In our continuation of the structure-based design of anti-trypanosomatid drugs, parasite-selective adenosine analogues were identified as low micromolar inhibitors of glyceraldehyde-3-phosphate dehydrogenase (GAPDH). Crystal structures of Trypanosoma brucei, Trypanosoma cruzi, Leishmania mexicana, and human GAPDH's provided details of how the
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