N1-(4,5-DICHLORO-2-NITROPHENYL)ACETAMIDE Chemical Properties

Melting point:

124-128 °C(lit.)

Boiling point:

418.4±45.0 °C(Predicted)

Density 

1.573±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

12.29±0.70(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C8H6Cl2N2O3/c1-4(13)11-7-2-5(9)6(10)3-8(7)12(14)15/h2-3H,1H3,(H,11,13)

InChIKey

ZEGRPTYRAGSSBH-UHFFFAOYSA-N

SMILES

C(NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O)(=O)C

CAS DataBase Reference

5462-30-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

HS Code 

2924190090

MSDS

• Language:English Provider:SigmaAldrich

N1-(4,5-DICHLORO-2-NITROPHENYL)ACETAMIDE Usage And Synthesis

Synthesis

The general procedure for the synthesis of N1-(4,5-dichloro-2-nitrophenyl)acetamide from N-(3,4-dichlorophenyl)acetamide was as follows: 3,4-dichloroacetanilide (II) (150 g, 0.74 mol) was slowly added to a reactor containing sulfuric acid (270 g, 99%, 2.7 mol) at 13 °C, stirred for 0.5 h and then cooled to 8 °C. Subsequently, fuming sulfuric acid (422 g, 31.1%, 4.61 mol) was slowly added to obtain a mixture. The sulfuric acid concentration of this mixture was 104%, where the molar ratio of 3,4-dichloroacetanilide (II) to sulfuric acid was 1:10. The mixture was further cooled to 3 °C and nitric acid (51 g, 98%, 0.79 mol) was slowly added over a period of 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC).3,4-Dichloroacetanilide was completely consumed within 1 h to give the product mixture. The product mixture was carefully poured into a mixture of 1650 g of ice with 200 ml of water, maintained at a temperature below 15 °C and stirred for 15 min to form a dispersion. The dispersion was filtered to give a residue containing 2-nitro-4,5-dichloroacetanilide (I). The residue was washed with water until no residual acid remained and dried to give 2-nitro-4,5-dichloroacetanilide (I) (174 g, yield = 95.23%, HPLC purity = 97.83%).HPLC analysis showed that the product contained 1.46% III.

References

[1] Patent: WO2018/91978, 2018, A1. Location in patent: Page/Page column 7-8
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792

N1-(4,5-DICHLORO-2-NITROPHENYL)ACETAMIDE(5462-30-6)Related Product Information

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