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Sigma-Aldrich

NMP

anhydrous, 99.5%

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

product name

1-Methyl-2-pyrrolidinone, anhydrous, 99.5%

grade

anhydrous

Quality Level

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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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.

Other Notes

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

Legal Information

Pure-Pac is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 1

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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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)
Stille couplings catalyzed by palladium-on-carbon with CuI as a cocatalyst: Synthesis of 2-(4'-acetylphenyl)thiophene
Liebeskind LS and Pe?a-Cabrera E
Organic Syntheses, 77, 135-135 (2000)
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
Miren Etxeberria-Benavides et al.
Membranes, 10(1) (2019-12-29)
The elimination of the additional defect healing post-treatment step in asymmetric hollow fiber manufacturing would result in a significant reduction in membrane production cost. However, obtaining integrally skinned polymeric asymmetric hollow fiber membranes with an ultrathin and defect-free selective layer
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

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