All Photos(3)

328634

Sigma-Aldrich

1-Methyl-2-pyrrolidinone

anhydrous, 99.5%

Synonym(s):
N-Methyl-2-pyrrolidone, 1-Methyl-2-pyrrolidone, NMP
Empirical Formula (Hill Notation):
C5H9NO
CAS Number:
Molecular Weight:
99.13
Beilstein:
106420
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

anhydrous

vapor density

3.4 (vs air)

vapor pressure

0.29 mmHg ( 20 °C)
0.99 mmHg ( 40 °C)

assay

99.5%

form

liquid

autoignition temp.

518 °F

expl. lim.

9.5 %

impurities

<0.005% water

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.)

density

1.028 g/mL at 25 °C (lit.)

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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Related Categories

Application

1-Methyl-2-pyrrolidinone may be used as a solvent in the following processes:
  • Preparation of 2-aryl and 2-alkyl benzothiazoles.
  • Ullmann coupling reaction of aryl halides and phenols to form Ullmann ethers in the presence of 2,2,6,6-tetramethylheptane-3,5-dione.
  • Stille cross-coupling reaction of aryl iodides with organostannanes catalyzed by Pd/C in the presence of copper iodide as cocatalyst.

Packaging

1, 6×1, 2, 4×2 L in Sure/Seal™
100, 12×100 mL in Sure/Seal™
50 L in Pure-Pac™ 2
18 L in Pure-Pac™ 1

Other Notes

Pure-Pac® II containers require the Micromatic MacroValve coupler for dispensing solvents, Z560723.

Legal Information

Pure-Pac is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK Germany

WGK 1

Flash Point(F)

195.8 °F - Pensky-Martens closed cup

Flash Point(C)

91 °C - Pensky-Martens closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Guohua Hu et al.
Nature communications, 8(1), 278-278 (2017-08-19)
Black phosphorus is a two-dimensional material of great interest, in part because of its high carrier mobility and thickness dependent direct bandgap. However, its instability under ambient conditions limits material deposition options for device fabrication. Here we show a black...
Densities, viscosities, speeds of sound, and relative permittivities for water+ cyclic amides (2-pyrrolidinone, 1-methyl-2-pyrrolidinone, and 1-vinyl-2-pyrrolidinone) at different temperatures.
George J and Sastry NV.
Journal of Chemical and Engineering Data, 49(2), 235-242 (2004)
Gerrit Homann et al.
iScience, 23(6), 101225-101225 (2020-06-21)
Frequently, poly(ethylene oxide) (PEO)-based solid polymer electrolytes (SPEs) reveal a failure with high-voltage electrodes, e.g. LiNi0.6Mn0.2Co0.2O2 in lithium metal batteries, which can be monitored as an arbitrary appearance of a "voltage noise" during charge and can be attributed to Li...
Preparation of 1-methoxy-2-(4-methoxyphenoxy)benzene
Buck E and Song ZJ
Organic Syntheses, 82, 69-69 (2005)
Effects of additional multiwall carbon nanotubes on impact behaviors of LiNi0.5Mn0.3Co0.2O2 battery electrodes.
Le AV, et al.
Journal of Applied Physics, 118(8), 085312-085312 (2015)

Articles

Greener Chemistry: Methods and Products for Amide Bond Formation

Amide bonds are ubiquitous in both nature and industrial applications. They are vital to the structure and function of biological macromolecules and polymers. The importance of this functionality has resulted in numerous approaches to its formation, ranging from stoichiometric activation of carboxylic acids to more recent advances in catalytic amide bond formation.

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