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M79204

Sigma-Aldrich

N-Methylpyrrolidine

97%

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Synonym(s):
1-Methylpyrrolidine, N-Methylpyrrolidine, N-Methyltetrahydropyrrole
Empirical Formula (Hill Notation):
C5H11N
CAS Number:
Molecular Weight:
85.15
Beilstein/REAXYS Number:
102445
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

liquid

bp

80-81 °C (lit.)

density

0.819 g/mL at 25 °C (lit.)

SMILES string

CN1CCCC1

InChI

1S/C5H11N/c1-6-4-2-3-5-6/h2-5H2,1H3

InChI key

AVFZOVWCLRSYKC-UHFFFAOYSA-N

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1 of 4

This Item
69110761990672718
vibrant-m

M79204

N-Methylpyrrolidine

vibrant-m

69110

1-Methylpyrrolidine

vibrant-m

761990

(R)-1-Methyl-2-pyrrolidinemethanol

vibrant-m

672718

1-Ethylpyrrolidine

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

density

0.819 g/mL at 25 °C (lit.)

density

0.800 g/mL at 20 °C (lit.)

density

0.971 g/mL at 25 °C

density

-

form

liquid

form

liquid

form

liquid

form

-

bp

80-81 °C (lit.)

bp

76-80 °C (lit.)

bp

68-71 °C (lit.)

bp

-

Application

N-Methylpyrrolidine can be used as a starting material to synthesize:
N-methyl pyrrolidine-zinc borohydride (ZBHNMP), a reducing agent for reduction of aldehydes, ketones, acid chlorides, and esters. ZBHNMP is also used in the reductive amination of aldehydes and ketones to their corresponding amines.
N-alkyl-N-methyl-pyrrolidinium bis(trifluoromethanesulfonyl)imide ionic liquids.
N-methylpyrrolidine-2-one hydrotribromide applicable as a catalyst for aziridination of alkenes.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Aquatic Chronic 2 - Flam. Liq. 2 - Skin Corr. 1A

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

-0.4 °F - closed cup

flash_point_c

-18 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Reductive amination of aldehydes and ketones to their corresponding amines with N-methylpyrrolidine zinc borohydride
Alinezhad H, et al.
Tetrahedron Letters, 50(6), 659-661 (2009)
N-methylpyrrolidine-2-one hydrotribromide: An efficient and new catalyst for the aziridination of alkenes using Chloramine-T under solvent free conditions
Jain SL, et al.
J. Mol. Catal. A: Chem., 256(1-2), 16-20 (2006)
N-Methylpyrrolidine-zinc borohydride: As a new stable and efficient reducing agent in organic synthesis
Tajbakhsh M, et al.
Synthetic Communications, 33(2), 229-236 (2003)
A R Salomon et al.
Biochemistry, 35(42), 13568-13578 (1996-10-22)
The 42-residues beta-(1-42) peptide is the major protein component of amyloid plaque cores in Alzheimer's disease. In aqueous solution at physiological pH, the synthetic beta-(1-42) peptide readily aggregates and precipitates as oligomeric beta-sheet structures, a process that occurs during amyloid
Burkhard Flick et al.
Toxicology and applied pharmacology, 237(2), 154-167 (2009-03-14)
N-methyl-2-pyrrolidone (NMP), which undergoes extensive biotransformation, has been shown in vivo to cause developmental toxicity and, especially after oral treatment, malformations in rats and rabbits. Data are lacking as to whether the original compound or one of its main metabolites

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