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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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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)
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)
Lijun Wei et al.
Carbohydrate research, 340(9), 1583-1590 (2005-06-01)
4'-Modified avermectin derivatives were designed and synthesized. Some of the new synthetic compounds showed excellent in vivo bioactivity against cabbage larvae when compared to commercially available avermectin B1a. In this synthesis, uncommon thioglycosyl sugar donors, prepared from the hydrolysis of
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