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Merck
CN

528218

N-Chlorophthalimide

96%

Synonym(s):

2-Chloro-1H-isoindole-1,3(2H)-dione, 2-Chloro-2,3-dihydro-1H-isoindole-1,3-dione, 2-Chloroisoindole-1,3-dione, 2-Chloroisoindoline-1,3-dione, Phthalimide chloride, Phthalimidoyl chloride

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About This Item

Empirical Formula (Hill Notation):
C8H4ClNO2
CAS Number:
3481-09-2
Molecular Weight:
181.58
NACRES:
NA.22
PubChem Substance ID:
24877568
UNSPSC Code:
12352100
EC Number:
222-459-8
MDL number:
MFCD00023027

Key Documents

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Product Name

N-Chlorophthalimide, 96%

InChI key

WDRFYIPWHMGQPN-UHFFFAOYSA-N

InChI

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

SMILES string

ClN1C(=O)c2ccccc2C1=O

assay

96%

mp

188-198 °C (lit.)

functional group

imide

Quality Level

100

Related Categories

Application

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ3818
MKCW8938
MKCX2531
MKCW9763
MKCV9920

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N Jayasree et al.
Talanta, 32(11), 1067-1068 (1985-11-01)
A stable new oxidimetric titrant, N-chlorophthalimide in anhydrous acetic acid, is proposed for direct titrations of a variety of simple and complex reductants such as As(III), Sb(III), Fe(II), ferrocyanide, iodide, ascorbic acid, hydroquinone, hydrazine, phenylhydrazine, benzhydrazide, isonicotinic acid hydrazide, semicarbazide
Development and a practical synthesis of nepafenac intermediate via modified Gassman reaction.
Cybulski M, et al.
Letters in Organic Chemistry, 9(7), 461-464 (2012)
N-Chlorophthalimide as a mild and efficient chlorination reagent in the Gassman ortho alkylation of aromatic amines. Synthesis of 3-(methylthio) oxindoles.
Cybulski M, et al.
Tetrahedron Letters, 55(40), 5423-5425 (2014)
Aminochlorination reaction with N-chlorophthalimide as a new nitrogen/chlorine source resulting in a-amino derivatives.
Qian Y, et al.
Tetrahedron, 68(31), 6198-6203 (2012)
Tertiary Butyl Hypochlorite as as N-Chlorinating Agent.
Zimmer H and Audrieth LF.
Journal of the American Chemical Society, 76(14), 3856-3857 (1954)
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