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N-Chlorophthalimide

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N-Chlorophthalimide manufacturers

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  • CAS:3481-09-2
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  • 2024-07-11
  • CAS:3481-09-2
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N-Chlorophthalimide Basic information
Product Name:N-Chlorophthalimide
Synonyms:N-CHLOROPHTHALIMIDE;Phthalimidoyl chloride;phthalimide chloride;2-chloro-1h-isoindole-1,3(2h)-dione;Chlorophtalimide;N-Chlorphthalimid;2-Chloro-2H-isoindole-1,3-dione;N-Chlorophthalimide,95%
CAS:3481-09-2
MF:C8H4ClNO2
MW:181.58
EINECS:222-459-8
Product Categories:Carbonyl Compounds;Cyclic Imides;Heterocycles;Chlorination;Halogenation;Organic Building Blocks;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Synthetic Organic Chemistry;3481-09-2
Mol File:3481-09-2.mol
N-Chlorophthalimide Structure
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
InChIInChI=1S/C8H4ClNO2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H
InChIKeyWDRFYIPWHMGQPN-UHFFFAOYSA-N
SMILESC1(=O)C2=C(C=CC=C2)C(=O)N1Cl
CAS DataBase Reference3481-09-2(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
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
N-Chlorophthalimide Usage And Synthesis
Chemical PropertiesWhite to pale yellow powder
UsesN-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 DescriptionN-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
1H-Isoindol-1-one, 3-hydroxy-

136918-14-4

N-Chlorophthalimide

3481-09-2

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 Preparation Products And Raw materials
Raw materialsPotassium phthalimide-->1H-Isoindol-1-one, 3-hydroxy--->Acetonitrile-->Lead tetraacetate-->Aluminum chloride
Preparation ProductsN-(4-Bromobutyl)phthalimide
Tag:N-Chlorophthalimide(3481-09-2) Related Product Information
Succinimide N-Chlorosuccinimide Thionyl chloride Bismaleimide Calcium chloride Oxalyl chloride Choline chloride Maleimide Ammonium chloride Sodium chloride Zinc chloride Potassium chloride Potassium phthalimide Phthalimide DIALIFOS Methylene Chloride Difluorochloromethane chloramide