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C0267

Sigma-Aldrich

2-Chloroacetamide

≥98%

Synonym(s):

Chloracetamide, alpha-Chloroacetamide

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About This Item

Linear Formula:
ClCH2CONH2
CAS Number:
79-07-2
Molecular Weight:
93.51
Beilstein:
878191
EC Number:
201-174-2
MDL number:
MFCD00008027
UNSPSC Code:
12352100
PubChem Substance ID:
57653974
NACRES:
NA.22

vapor pressure

0.05 mmHg ( 20 °C)

Assay

≥98%

form

powder

mp

116-118 °C (lit.)

SMILES string

NC(=O)CCl

InChI

1S/C2H4ClNO/c3-1-2(4)5/h1H2,(H2,4,5)

InChI key

VXIVSQZSERGHQP-UHFFFAOYSA-N

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Application

2-Chloroacetamidecan be used as a reactant to synthesize:
  • 2-Amino-4-chloroquinolines via o-alkylation of 4-chloro-1H-quinolin-2-ones and subsequent Smiles rearrangement.
  • 2-(Formylaryloxy)acetamides by reacting with hydroxybenzaldehydes in the presence of potassium carbonate as a base.
  • Biarylamine derivatives via aluminum triflate-catalyzed direct amination of benzhydrols.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H317,H361f

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2 - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

338.0 °F

Flash Point(C)

170 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6938V
WXBD6050V
WXBD5784V
WXBD5638V
WXBD5164V

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Cleonice Rocha et al.
Environmental pollution (Barking, Essex : 1987), 152(1), 239-244 (2007-07-17)
Solid-phase microextraction coupled with gas chromatography-mass spectrometry (SPME-GC-MS) was used to analyze two triazine (atrazine and simazine) and three chloroacetamide herbicides (acetochlor, alachlor, and metolachlor) in water samples from a midwest US agricultural drainage ditch for two growing seasons. The
Jun Zhang et al.
Journal of agricultural and food chemistry, 59(9), 4614-4621 (2011-03-23)
A butachlor-degrading strain, designated FLY-8, was isolated from rice field soil and was identified as Paracoccus sp. Strain FLY-8 could degrade and utilize six chloroacetamide herbicides as carbon sources for growth, and the degradation rates followed the order alachlor >
Felix Boos et al.
Nature cell biology, 21(4), 442-451 (2019-03-20)
The cytosolic accumulation of mitochondrial precursors is hazardous to cellular fitness and is associated with a number of diseases. However, it is not observed under physiological conditions. Individual mechanisms that allow cells to avoid cytosolic accumulation of mitochondrial precursors have
K Eszter Borbas et al.
Bioconjugate chemistry, 18(4), 1205-1212 (2007-06-23)
Targeted radiopharmaceuticals offer the possibility of improved tumor imaging and radiotherapy, with reduced side effects. A variety of monoclonal antibodies and antibody fragments have previously been successfully radiolabeled and used in diagnostic imaging and targeted radiotherapy of cancer. Many such
Michelle L Hladik et al.
Environmental science & technology, 39(17), 6561-6574 (2005-09-30)
Although laboratory studies have revealed that many different neutral degradates of chloroacetamide herbicides can form during thermochemical, biological, and photochemical transformations, relatively few have been sought in the environment, despite their likely generation in appreciable amounts, relative persistence, and known
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