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/REAXYS Number:
106420
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

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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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

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

WGK Germany

WGK 1

Flash Point(F)

195.8 °F - Pensky-Martens closed cup

Flash Point(C)

91 °C - Pensky-Martens closed cup

Certificate of Analysis

Certificate of Origin

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