2-Chloro-N-(2,6-dimethylphenyl)acetamide Chemical Properties

Melting point:

150-151 °C(lit.)

Boiling point:

316.8±30.0 °C(Predicted)

Density 

1.1363 (rough estimate)

refractive index 

1.5330 (estimate)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

12.91±0.70(Predicted)

form 

Crystalline Powder or Needles

color 

White to brown

Water Solubility 

Soluble in Chloroform, Methanol. Insoluble in water.

BRN 

781309

Stability:

Light Sensitive

InChIKey

FPQQSNUTBWFFLB-UHFFFAOYSA-N

CAS DataBase Reference

1131-01-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Chloro-2',6'-acetoxylidide(1131-01-7)

EPA Substance Registry System

Acetamide, 2-chloro-N-(2,6-dimethylphenyl)- (1131-01-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29214200

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-N-(2,6-dimethylphenyl)acetamide Usage And Synthesis

Chemical Properties

beige needles or crystalline powder

Uses

Lidocaine intermediate.

Uses

2-Chloro-2',6'-dimethylacetanilide is used in the determination of the enantiomers of tocainide in blood plasma by gas-liquid chromatography with electron-capture detection. It is a nonsteroidal antinflammatory drug.

General Description

N-(2,6-Dimethylphenyl)chloroacetamide (2-chloro-2′,6′-acetoxylidide) is nonsteroidal antinflammatory drug.

Synthesis

General method: Chloroiodomethane (1.5 eq.) is slowly added to a solution of 2,6-dimethylphenyl isocyanate (1.0 eq.) in anhydrous ether (1 M concentration) at -78 °C. After 2 minutes of reaction, a 1.5 M solution of methyl lithium-lithium bromide (1.25 equiv.) ether was added dropwise over 5 minutes. Maintaining this temperature, the reaction mixture was stirred for the indicated time (see Table 1 and Scheme 2 for specific times). Upon completion of the reaction, aqueous ammonium chloride solution (2 mL/mmol substrate) was added, the cooling bath was removed, and stirring was continued until the mixture was brought to room temperature. Subsequently, the reaction mixture was extracted with ether (2 x 5 mL) and the organic phase was washed sequentially with water (5 mL) and brine (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give pure 2,6-dimethylchloroacetanilide.

References

[1] Chemical Communications, 2013, vol. 49, # 75, p. 8383 - 8385
[2] Synthesis (Germany), 2014, vol. 46, # 21, p. 2897 - 2909

2-Chloro-N-(2,6-dimethylphenyl)acetamide(1131-01-7)Related Product Information

• Chloroacetamide
• 4'-Nitroacetanilide
• 2-BENZOYLACETANILIDE
• 4'-Aminoacetanilide
• N,N-Dimethyl-1,4-phenylenediamine
• N-Acetylsulfanilyl chloride
• N,N-Dimethylaniline
• p-Acetotoluidide
• Acetaminophen
• Acetamide
• N,N-Dimethylacetamide
• Difluorochloromethane
• Metazachlor
• Machette
• Alachlor
• DIETHATYL ETHYL
• Metolachlor
• DIMETHACHLOR