N-Methylphthalimide Chemical Properties

Melting point:

129-132 °C (lit.)

Boiling point:

286.05°C

Density 

1.2443 (rough estimate)

refractive index 

1.4500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

-2.09±0.20(Predicted)

color 

White to Off-White

BRN 

124428

CAS DataBase Reference

550-44-7(CAS DataBase Reference)

NIST Chemistry Reference

1H-Isoindole-1,3(2H)-dione, 2-methyl-(550-44-7)

EPA Substance Registry System

1H-Isoindole-1,3(2H)-dione, 2-methyl- (550-44-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

1

RTECS 

TI5602700

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29251900

MSDS

• Language:English Provider:N-Methylphthalimide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-Methylphthalimide Usage And Synthesis

Chemical Properties

White powder

Uses

Photoreduction of N-methylphthalimide (NMP) with 2,3-dimethyl-2-butene h and the selective electroreduction of N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one have been studied.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 497, 1979 DOI: 10.1021/jo01318a005

General Description

Photoreduction of N-methylphthalimide (NMP) with 2,3-dimethyl-2-butene has been studied. The selective electroreduction of N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one in ionic liquids and phenol as a proton donor under silent and ultrasonic conditions has been reported. Single electron transfer (SET)-induced photochemical reaction of NMP with silyl enol ether has been investigated. Nitration of NMP is reported to afford “exclusively” 3-nitro-derivative.

Purification Methods

Recrystallise the imide from absolute EtOH or AcOH (m 134o). The IR has max at 1780 and 1380cm -1. [Beilstein 21 H 461, 21 III/IV 5030.]

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