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422835

Sigma-Aldrich

2-Chloro-N-(hydroxymethyl)acetamide

98%

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About This Item

Fórmula lineal:
ClCH2CONHCH2OH
Número de CAS:
2832-19-1
Peso molecular:
123.54
EC Number:
220-598-9
MDL number:
MFCD00021961
UNSPSC Code:
12352100
PubChem Substance ID:
24866457
NACRES:
NA.22

assay

98%

mp

100-105 °C (lit.)

SMILES string

OCNC(=O)CCl

InChI

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

InChI key

TXNSZCSYBXHETP-UHFFFAOYSA-N

Categorías relacionadas

General description

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).

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Wim H De Jong et al.
Journal of immunotoxicology, 4(3), 239-246 (2008-10-30)
In the Local Lymph Node Assay (LLNA), a stimulation index of 3 (SI = 3) is established as a threshold value for hazard identification of sensitization. The corresponding EC3 value, the effective concentration inducing a threefold increase compared to controls
Occupational contact dermatitis to N-methylol-chloracetamide.
M Farli et al.
Contact dermatitis, 17(3), 182-184 (1987-09-01)
The amidomethylation of some N, N-dialkylanilines (Tscherniac-Einhorn reaction).
Gale DJ and Wilshire JFK.
Australian Journal of Chemistry, 28(11), 2447-2458 (1975)
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
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
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