2-chloroacetamide

Structural formula
General
Surname	2-chloroacetamide
other names	Chloroacetic acid amide Chloroacetamide α-chloroacetamide 2-chloroacetamide ( IUPAC ) Chloroethanamide CHLOROACETAMIDE ( INCI )
Molecular formula	C 2 H 4 ClNO
Brief description	colorless and odorless crystals
External identifiers / databases
CAS number 79-07-2 EC number 201-174-2 ECHA InfoCard 100.001.068 PubChem 6580 Wikidata Q209345
properties
Molar mass	93.5 g mol −1
Physical state	firmly
Melting point	119-120 ° C
boiling point	135 ° C (decomposition)
Vapor pressure	0.07 hPa (20 ° C)
solubility	readily soluble in water: 90 g l −1 (20 ° C) Easily soluble in dimethyl sulfoxide and dimethyl formamide easily soluble in isopropanol : 40 g l −1 (20 ° C) readily soluble in butanol : 35 g l −1 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 301-317-361f P: 201-280-301 + 310 + 330-308 + 313-333 + 313
Toxicological data	138 mg kg −1 ( LD 50 ,  rat ,  oral ) 150 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-chloroacetamide is a chemical compound from the group of carboxamides and organic chlorine compounds .

Extraction and presentation

2-chloroacetamide can be obtained by reacting ethyl chloroacetate with ammonia or chloroacetyl chloride with ammonium acetate .

properties

2-chloroacetamide is a flammable solid that is readily soluble in water. Its aqueous solution is acidic. With acids and bases, hydrolytic decomposition occurs, the compound being relatively stable in the pH range between 4 and 9. At pH 8, the half-life of the decomposition is 108 days. At temperatures above 135 ° C the compound decomposes, producing carbon monoxide , carbon dioxide , nitrogen oxides and hydrogen chloride . The decomposition is strongly exothermic with a heat of decomposition of −63 kJ mol ⁻¹ or −670 kJ kg ⁻¹ .

use

2-chloroacetamide is widely used as a biocide and preservative (e.g. in cosmetics, pharmaceuticals, shoe polish, adhesives, household cleaners and industrial oils).

safety instructions

2-chloroacetamide is classified as a contact allergen , with the frequency of sensitization being occasional and the potential for sensitization being high.

Related links

• Fluoroacetamide

Individual evidence

1. ↑ Entry on CHLOROACETAMIDE in the CosIng database of the EU Commission, accessed on March 11, 2020.
2. ↑ ^{a b c d e f} Entry on 2-chloroacetamide. In: Römpp Online . Georg Thieme Verlag, accessed on November 2, 2016.
3. ↑ ^{a b c d e f} Entry on 2-chloroacetamide in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
4. ↑ ^{a b c d e f g h} Toxicological assessment of chloracetamide (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
5. ↑ Entry on 2-chloroacetamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
6. ↑ PG Urben; MJ Pitt: Bretherick's Handbook of Reactive Chemical Hazards . 6th Edition, Vol. 1, Butterworth / Heinemann 1999, ISBN 0-7506-3605-X , p. 293.
7. ↑ Grewer, T .; Klais, O .: Exothermic decomposition - investigations of the characteristic material properties , VDI-Verlag, series "Humanisierung des Arbeitsleben", Volume 84, Düsseldorf 1988, ISBN 3-18-400855-X , p. 9.