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69110

Sigma-Aldrich

1-Methylpyrrolidine

≥98.0% (GC)

Synonym(s):

N-Methylpyrrolidine, N-Methyltetrahydropyrrole

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About This Item

Empirical Formula (Hill Notation):
C5H11N
CAS Number:
Molecular Weight:
85.15
Beilstein:
102445
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.0% (GC)

form

liquid

refractive index

n20/D 1.425

bp

76-80 °C (lit.)

density

0.800 g/mL at 20 °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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Application

1-Methylpyrrolidine is extensively used in the synthesis of pyrrolidine based ionic liquids. Some of the other reported applications include:
  • Synthesis of ionic liquid electrolytes for primary Li/CFx batteries.
  • Preparation of ionic liquid as a reaction medium to carry out sulfuric acid-catalyzed conversion of alkynes to ketones.
  • MCM-47, a highly crystalline ferrierite layered silicate, can be synthesized using a diquaternary ammonium salt prepared from the reaction of 1-methylpyrrolidine with 1,4-dibromobutane.

Signal Word

Danger

Hazard Statements

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

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Structure and properties of high stability geminal dicationic ionic liquids.
Anderson J L, et al.
Journal of the American Chemical Society, 127(2), 593-604 (2005)
Ionic liquid electrolytes for lithium batteries: Synthesis, electrochemical, and cytotoxicity studies.
Madria N, et al.
Journal of Power Sources, 234, 277-284 (2013)
MCM-47: a highly crystalline silicate composed of hydrogen-bonded ferrierite layers.
Burton A, et al.
Chemistry of Materials, 12(10), 2936-2942 (2000)
N-Methyl-N-propylpiperidinium bis (trifluoromethanesulfonyl) imide (PP13?TFSI)?novel electrolyte base for Li battery.
Sakaebe H and Matsumoto H
Electrochemical Communications, 5(7), 594-598 (2003)
Sulfuric acid-catalyzed conversion of alkynes to ketones in an ionic liquid medium under mild reaction conditions.
Wong W L, et al.
ACS Catalysis, 1(2), 116-119 (2011)

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