N-Chlorophthalimide Chemical Properties

Melting point:

188-198 °C (lit.)

Boiling point:

315.1±25.0 °C(Predicted)

Density 

1.56±0.1 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

-3.53±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C8H4ClNO2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H

InChIKey

WDRFYIPWHMGQPN-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC=C2)C(=O)N1Cl

CAS DataBase Reference

3481-09-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

1759

WGK Germany 

1

HazardClass 

8

PackingGroup 

II

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

N-Chlorophthalimide Usage And Synthesis

Chemical Properties

White to pale yellow powder

Uses

N-Chlorophthalimide may be employed in the synthesis of:

• α-amino acetal
• α-amino nitro compounds
• vicinal diamine
• α,β-unsaturated vicinal haloamino nitro compound

It may also be used as a chlorination reagent for the synthesis of 3-(methylthio)oxindoles.

General Description

N-Chlorophthalimide in anhydrous acetic acid serves as a useful oxidizing reagent for use in various direct titrimetric analyses. N-Chlorophthalimide can be synthesized by reacting phthalimide, t-butyl hypochlorite, water and t-butyl alcohol. It participates in the synthesis of 2-amino-3-benzoyl-α-(methylthio)phenylacetamide.

Synthesis

General procedure for the synthesis of N-chlorophthalimide from 3-hydroxy-1H-isoindol-1-one: Anhydrous aluminum trichloride (AlCl3, 1 eq., 10 mmol, 1.36 g) was added to an anhydrous acetonitrile (CH3CN, 100 mL) solution of lead tetraacetate (Pb(OAc)4, 1 eq., 10 mmol, 4.52 g). The mixture was stirred at room temperature for 5 minutes before phthalimide (1 eq., 10 mmol, 1.5 g) was added. The resulting mixture was gently refluxed under nitrogen protection for 20 h and subsequently cooled to room temperature. The solvent was removed by rotary evaporation and the crude product was purified by column chromatography using pure dichloromethane (DCM) as eluent. Yield: 1.32 g, 71% yield.1H NMR (300 MHz, CDCl3): δ 7.94-7.91 (m, 2H), 7.82-7.79 (m, 2H) ppm.

References

[1] Synthesis, 2009, # 16, p. 2797 - 2801
[2] Synlett, 2006, # 2, p. 194 - 200
[3] Catalysis Today, 2018, vol. 308, p. 94 - 101
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 1302
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 8, p. 163

N-Chlorophthalimide(3481-09-2)Related Product Information

• O-Phthalimide
• Potassium phthalimide
• Succinimide
• Thionyl chloride
• Bismaleimide
• Calcium chloride
• Oxalyl chloride
• Choline chloride
• Maleimide
• Ammonium chloride
• Sodium chloride
• Zinc chloride
• N-Chlorosuccinimide
• Potassium chloride
• DIALIFOS
• Methylene Chloride
• Difluorochloromethane
• chloramide