407992

Sigma-Aldrich

N-Methylphthalimide

98%

Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
Molecular Weight:
161.16
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

129-132 °C (lit.)

SMILES string

CN1C(=O)c2ccccc2C1=O

InChI

1S/C9H7NO2/c1-10-8(11)6-4-2-3-5-7(6)9(10)12/h2-5H,1H3

InChI key

ZXLYYQUMYFHCLQ-UHFFFAOYSA-N

Related Categories

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.

Packaging

5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Photoreduction of N-methylphthalimide with 2, 3-dimethyl-2-butene. Evidence for reaction through an electron transfer generated ion pair.
Mazzocchi PH and Klingler L.
Journal of the American Chemical Society, 106(24), 7567-7572 (1984)
Nitration of N-alkylphthalimides.
Williams FJ and Donahue PE.
The Journal of Organic Chemistry, 43(8), 1608-1610 (1978)
Constanza Villagrán et al.
Ultrasonics sonochemistry, 12(6), 423-428 (2005-04-26)
The selective electroreduction N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one has been performed in ionic liquids using phenol as a proton donor under silent and ultrasonic conditions. A significant increase in the rate of electroreduction is shown using ultrasonic activation and in addition high...
Single electron transfer induced photoaddition reactions of silyl enol ether to N-methylphthalimide.
Oh SW, et al.
Bull. Korean Chem. Soc., 28(4), 629-629 (2007)

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