N-Methylsuccinimide

Name: <I>N</I>-Methylsuccinimide
Brand: ALDRICH

99%

Synonym(s):

1-Methyl-2,5-pyrrolidinedione, N-Methyl-2,5-pyrrolidinedione

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About This Item

Empirical Formula (Hill Notation):

C₅H₇NO₂

CAS Number:

1121-07-9

Molecular Weight:

113.11

MDL number:

MFCD00005517

UNSPSC Code:

12352100

PubChem Substance ID:

24859505

NACRES:

NA.22

Key Documents

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Quality Level

100

assay

99%

form

solid

bp

234-235 °C (lit.)

mp

61-70 °C (lit.)

functional group

imide

SMILES string

CN1C(=O)CCC1=O

InChI

1S/C5H7NO2/c1-6-4(7)2-3-5(6)8/h2-3H2,1H3

InChI key

KYEACNNYFNZCST-UHFFFAOYSA-N

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Chemistry & Biochemicals

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This Item	345415	276170	569534
Sigma-Aldrich 325384 N-Methylsuccinimide	Sigma-Aldrich 345415 N-Methoxy-N-methylbenzamide	Sigma-Aldrich 276170 N,N-Dimethylbenzamide	Sigma-Aldrich 569534 Methanol-d₄
assay 99%	assay 98%	assay 99%	assay ≥99% (CP)
Quality Level 100	Quality Level 100	Quality Level 200	Quality Level 200
bp 234-235 °C (lit.)	bp 70 °C/0.1 mmHg (lit.)	bp 132-133 °C/15 mmHg (lit.)	bp 65.4 °C (lit.)
mp 61-70 °C (lit.)	mp -	mp 43-45 °C (lit.)	mp -99 °C (lit.)
form solid	form liquid	form solid	form liquid
functional group imide	functional group amine, phenyl	functional group amide, phenyl	functional group -

General description

N-Methylsuccinimide is a metabolite of N-methyl-2-pyrrolidone (NMP) and its presence in in plasma and urine can be used as a biomarker of exposure to NMP.[1] Hydrogen bonded complexes between N-methylsuccinimide and phenols (pKa = 10.2 → 6) are investigated by infrared spectrometry.[2]

Application

N-Methylsuccinimide was employed as model compound to investigate the mechanism of enolization step by density-functional theory (DFT) calculations.[3]

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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nfrared Study of the Hydrogen Bond Complexes Between N-Methylsuccinimide and Phenols.

Bruyneel K, et al.

Spectroscopy Letters, 29(4), 739-747 (1996)

N-Methylsuccinimide in plasma and urine as a biomarker of exposure to N-methyl-2-pyrrolidone.

Jonsson BAG and ?kesson B.

International Archives of Occupational and Environmental Health, 74(4), 289-294 (2004)

Modeling the enolization of succinimide derivatives, a key step of racemization of aspartic acid residues: importance of a two-H2O mechanism.

Ohgi Takahashi et al.

Chemistry & biodiversity, 7(6), 1349-1356 (2010-06-22)

Racemization of aspartic acid residues in peptides and proteins is assumed to proceed via succinimide intermediates. An enolization of the succinimide intermediate is required for the racemization to occur. In this study, we modeled the enolization step by density-functional theory

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