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328634 Sigma-Aldrich

1-Methyl-2-pyrrolidinone

anhydrous, 99.5%

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

  • CAS Number 872-50-4

  • Empirical Formula (Hill Notation) C5H9NO

  • Molecular Weight 99.13

  •  Beilstein/REAXYS Number 106420

  •  EC Number 212-828-1

  •  MDL number MFCD00003193

  •  PubChem Substance ID 57648684

  •  NACRES NA.21

Purchase

Properties

Related Categories Anhydrous, Anhydrous Solvents, Returnable Containers, Solvent Bottles, Solvent Packaging Options,
Quality Level   200
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

Description

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™

18 L in Pure-Pac™ 1

View returnable container options.

100, 12×100 mL in Sure/Seal™

50 L in Pure-Pac™ 2

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
WGK Germany 
WGK 1
RTECS 
UY5790000
Flash Point(F) 
195.8 °F - Pensky-Martens closed cup
Flash Point(C) 
91 °C - Pensky-Martens closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Anhydrous Solvents for Coupling Reactions

Due to the sensitivity to air and moisture, coupling reactions often require relatively low air and water conditions to initiate the reaction. Therefore, the use of anhydrous solvents is highly recom...
Keywords: Coupling reactions, Cross couplings, Negishi Coupling, Solvents

Anhydrous Solvents for Organic and Organometallic Chemistry

Many well-known reactions require water-free conditions to initiate or complete the reaction. Failure to include anhydrous solvents can result in low product yield or reaction failure. As the market ...
Keywords: Acylations, Alkylations, Electrophilic aromatic substitution, Formylations, Grignard Reaction, Solvents, Substitutions, Vilsmeier-Haack reaction

Pressure-Temperature Calculator for Solvents

*Calculations provide estimated results based on Antoine's Coefficients and their associated temperature range values. Antoine's Coefficients were obtained from the National Institute of Standards an...

The First Negishi Cross-Coupling Reaction of Two Alkyl Centers Utilizing a Pd-N-Heterocyclic Carbene (NHC) Catalyst

The development of an NHC-based system capable of cross-coupling sp3-sp3 centers in high yield has been a long-standing challenge. This communication describes the use of a Pd-NHC catalytic system th...
Keywords: Catalysis, Chromatography, Cross couplings, Flash chromatography

Peer-Reviewed Papers
15

References

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