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328634

Sigma-Aldrich

NMP

anhydrous, 99.5%

Synonym(s):

1-Methyl-2-pyrrolidone, N-Methyl-2-pyrrolidone, NMP

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About This Item

Empirical Formula (Hill Notation):
C5H9NO
CAS Number:
Molecular Weight:
99.13
Beilstein:
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

Signal Word

Danger

Hazard Statements

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

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

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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
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)
Preparation of 1-methoxy-2-(4-methoxyphenoxy)benzene
Buck E and Song ZJ
Organic Syntheses, 82, 69-69 (2005)
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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