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422835

Sigma-Aldrich

2-Chloro-N-(hydroxymethyl)acetamide

98%

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About This Item

Linear Formula:
ClCH2CONHCH2OH
CAS Number:
2832-19-1
Molecular Weight:
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

Related Categories

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

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

422835-1G:
422835-5G:
422835-BULK:
422835-VAR:
422835-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF7983
MKBS1048V
MKBS2043V
MKBM1267V
MKBK4368V

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Allergic contact dermatitis from the preservative N-methylol-chloracetamide.
S Agren et al.
Contact dermatitis, 6(4), 302-303 (1980-06-01)
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
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
The amidomethylation of some N, N-dialkylanilines (Tscherniac-Einhorn reaction).
Gale DJ and Wilshire JFK.
Australian Journal of Chemistry, 28(11), 2447-2458 (1975)
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