N-ISOPROPYL-2-CHLOROACETAMIDE

N-ISOPROPYL-2-CHLOROACETAMIDE Property

Melting point:

58-60°C

Boiling point:

250.6±23.0 °C(Predicted)

Density 

1.052±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Acetone, Chloroform, Dichloromethane, DMSO, Ethyl Acetate, Methanol

pka

14.08±0.46(Predicted)

form 

Solid

color 

Dark Brown

BRN 

1745034

InChI

InChI=1S/C5H10ClNO/c1-4(2)7-5(8)3-6/h4H,3H2,1-2H3,(H,7,8)

InChIKey

GYPNJSBBOATUPK-UHFFFAOYSA-N

SMILES

C(NC(C)C)(=O)CCl

CAS DataBase Reference

2895-21-8(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2924190090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

N-ISOPROPYL-2-CHLOROACETAMIDE Chemical Properties,Usage,Production

Uses

2-Chloro-N-isopropylacetamide is an intermediate in synthesizing Prothoate (P838810), which can be used as analyte in analytical study of a new method of detecting multi-residue of organophosphorus pesticide.

Synthesis

The general procedure for the synthesis of N-isopropylchloroacetamide from isopropylamine and chloroacetyl chloride was as follows: isopropylamine (236.4 mg, 4.0 mmol) was dissolved in 4 mL of dichloromethane, followed by the addition of anhydrous potassium carbonate (663.4 mg, 4.8 mmol). The reaction flask was cooled in an ice bath and chloroacetyl chloride (451.8 mg, 4.0 mmol) was slowly added dropwise through a dropping funnel. After the dropwise addition, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, 10 mL of ice water was added to quench the reaction. The aqueous phase was extracted with dichloromethane and the organic phases were combined, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give a white solid product without further purification. The yield was 70.3%.

References

[1] Journal of Organic Chemistry, 2012, vol. 77, # 9, p. 4261 - 4270
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 1106 - 1114
[3] ChemistryOpen, 2014, vol. 3, # 6, p. 238 - 241
[4] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 6, p. 678 - 681
[5] Patent: CN106146414, 2016, A. Location in patent: Paragraph 0472; 0473; 0474