N-Methylphthalimide

CAS NO.：550-44-7
Empirical Formula: C9H7NO2
Molecular Weight: 161.16
MDL number: MFCD00023063
EINECS: 208-982-4
SAFETY DATA SHEET (SDS)
Update Date: 2023-04-27 16:27:43

What is N-Methylphthalimide?

Chemical properties

White powder

The Uses of N-Methylphthalimide

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.

Synthesis

N-methylphthalimide (NMP) was synthesized from phthalic anhydride (PA) and dimethyl carbonate (DMC) with N,N-dimethylformamide (DMF) as solvent and tetrabutylamonium bromide (TBBA) as phase transfer catalyst (PTC).

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.]

Properties of N-Methylphthalimide

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 for N-Methylphthalimide

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.