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443778

Sigma-Aldrich

1-Methyl-2-pyrrolidinone

ACS reagent, ≥99.0%

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Synonym(s):
1-Methyl-2-pyrrolidone, N-Methyl-2-pyrrolidone, NMP
Empirical Formula (Hill Notation):
C5H9NO
CAS Number:
872-50-4
Molecular Weight:
99.13
Beilstein:
106420
EC Number:
212-828-1
MDL number:
MFCD00003193
UNSPSC Code:
12352005
PubChem Substance ID:
329756501
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

vapor density

3.4 (vs air)

vapor pressure

0.29 mmHg ( 20 °C)
0.99 mmHg ( 40 °C)

Assay

≥99.0%

form

liquid

autoignition temp.

518 °F

expl. lim.

9.5 %

impurities

≤0.01% Free amines (as CH3NH2)
≤0.05% water

color

APHA: ≤50

refractive index

n20/D 1.47 (lit.)

pH

7.7-10.0 (20 °C, 100 g/L)

bp

202 °C (lit.)
81-82 °C/10 mmHg (lit.)

mp

−24 °C (lit.)

solubility

acetone: miscible(lit.)
alcohol: miscible(lit.)
benzene: miscible(lit.)
chloroform: miscible(lit.)
ethyl acetate: miscible(lit.)
water: miscible(lit.)

density

1.028 g/mL at 25 °C (lit.)

anion traces

chloride (Cl-): ≤1 ppm

SMILES string

CN1CCCC1=O

InChI

1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3

InChI key

SECXISVLQFMRJM-UHFFFAOYSA-N

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Application

1-Methyl-2-pyrrolidinone may be used as:
  • An alternative eluent to THF in the size exclusion chromatography (SEC) based resolution of coal-derived liquids.
  • Reaction medium to prepare 2-aryl and 2-alkyl benzothiazoles.
  • A solvent in the ultrasonic preparation of metal organic framework (MOF-177) crystals.
It may be used to synthesize single-phase chalcopyrite CuInSe2 nanocrystals and potassium 3-methyl-2-oxo-pyrrolidinenitronate.

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Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H335,H360D

Hazard Classifications

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 1

Certificates of Analysis (COA)

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Alkyl nitrate nitration of active methylene-compounds. 15. Nitration of 1-methyl-4-piperidone, 1-methyl-2-pyrrolidinone and 1,3-dimethyl-2-pyrrolidinone.
Feuer H, et al.
Journal of Heterocyclic Chemistry, 16(3), 481-485 (1979)
A Green and Air Pressure Solution Synthesis of CuInSe2 Nanocrystals Using 1-methyl-2-Pyrrolidinone as Hot Solvent.
Wang W, et al.
Journal of the American Ceramic Society. American Ceramic Society, 94(8), 2571-2577 (2011)
Aneuploidy induction in Saccharomyces cerevisiae by two solvent compounds, 1-methyl-2-pyrrolidinone and 2-pyrrolidinone.
Mayer VW, et al.
Environmental and Molecular Mutagenesis, 11(1), 31-40 (1988)
Solubility limitations in the determination of molecular mass distributions of coal liquefaction and hydrocracking products: 1-methyl-2-pyrrolidinone as mobile phase in size exclusion chromatography.
Herod AA, et al.
Energy and Fuels, 10(3), 743-750 (1996)
Da-Won Jung et al.
Dalton transactions (Cambridge, England : 2003), 39(11), 2883-2887 (2010-03-05)
High quality MOF-177 crystals in the size range of 5-20 microm were successfully synthesized via a sonochemical route in a substantially reduced synthesis time (40 min) in the presence of low-cost NMP (1-methyl-2-pyrrolidone) as a solvent. Microwave heating in NMP
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