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M79204

Sigma-Aldrich

N-Methylpyrrolidine

97%

Synonym(s):

1-Methylpyrrolidine, N-Methylpyrrolidine, N-Methyltetrahydropyrrole

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About This Item

Empirical Formula (Hill Notation):
C5H11N
CAS Number:
120-94-5
Molecular Weight:
85.15
Beilstein:
102445
EC Number:
204-438-5
MDL number:
MFCD00003173
UNSPSC Code:
12352100
PubChem Substance ID:
24897203
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

Related Categories

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.

Signal Word

Danger

Hazard Statements

H225,H301,H314,H332,H411

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-0.4 °F - closed cup

Flash Point(C)

-18 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Effect of the alkyl group on the synthesis and the electrochemical properties of N-alkyl-N-methyl-pyrrolidinium bis (trifluoromethanesulfonyl) imide ionic liquids
Appetecchi GB, et al.
Electrochimica Acta, 54(4), 1325-1332 (2009)
Hsiu-Li Su et al.
Journal of chromatography. A, 1216(27), 5313-5319 (2009-05-26)
This paper describes a sweeping-micellar electrokinetic chromatography (sweeping-MEKC) technique for the determination of seven benzodiazepines, using, as sweeping carriers, the ionic liquid-type cationic surfactants 1-cetyl-3-methylimidazolium bromide (C(16)MIMBr) and N-cetyl-N-methylpyrrolidinium bromide (C(16)MPYB). These surfactants resemble the commonly employed cationic surfactant cetyltrimethylammonium
Vincent P Schnee et al.
Electrophoresis, 27(21), 4141-4148 (2006-11-01)
MEKC and linear solvation free energy relationships (LSFERs) have been used to characterize the solute distribution between water and self-assemblies formed from ionic liquid type mono-chain cationic surfactants containing a cyclic pyrrolidinium head group. Several features of the solvation environment
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