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394238

Sigma-Aldrich

Pyrrolidine

≥99.5%, purified by redistillation

Synonym(s):

Tetrahydropyrrole, Tetramethyleneimine

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About This Item

Empirical Formula (Hill Notation):
C4H9N
CAS Number:
123-75-1
Molecular Weight:
71.12
Beilstein:
102395
EC Number:
204-648-7
MDL number:
MFCD00005249
UNSPSC Code:
12352100
PubChem Substance ID:
24864581
NACRES:
NA.22

vapor density

2.45 (vs air)

vapor pressure

128 mmHg ( 39 °C)
49 mmHg ( 20 °C)

Assay

≥99.5%

form

liquid

autoignition temp.

653 °F

purified by

redistillation

expl. lim.

10.6 %

refractive index

n20/D 1.443 (lit.)

solubility

water: miscible

density

0.852 g/mL at 25 °C (lit.)

SMILES string

C1CCNC1

InChI

1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2

InChI key

RWRDLPDLKQPQOW-UHFFFAOYSA-N

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General description

Pyrrolidine is a five membered cyclic amine. It is a nitrogen heterocycle that forms the nucleus of various bioactive molecules. It can be synthesized by reacting 1,4-diaminobutanes with acids. It behaves as a strong base in employed in certain homogeneous nonaqueous reactions. Its crystalline structure has been investigated. Its reaction on the Ge(100)-2×1 surface and Si(100)-2×1 surface has been investigated. Pyrrolidine has been found to be one of the component of volatile amine fraction in the brewing process. A study on the kinetics of pyrrolidinolysis of phthalimide (PTH) shows second- and third-order terms in the rate law. Biodegradation of pyrrolidine by Mycobacterium strains has been studied.

Application

Pyrrolidine may be used in the following studies:
  • Synthesis of pyrrolidine derivatives of pyrimidine.
  • As a catalyst in the selective monoallylation of allylic alcohols.
  • To capture carbondioxide in a bubble column reactor using pyrrolidine aqueous solutions by gas–liquid absorption.

Signal Word

Danger

Hazard Statements

H225,H302 + H332,H314

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

37.4 °F - closed cup

Flash Point(C)

3 °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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Kinetic studies of the reactions of phthalimide with ammonia and pyrrolidine.
Khan MN and Ohayagha JE.
Journal of Physical Organic Chemistry, 7(9), 518-524 (1994)
Volatile amines in the brewing process. The identification and occurrence of pyrrolidine.
Slaughter JC.
Journal of the Institute of Brewing, 76(1), 22-25 (1970)
Five-Membered Nitrogen Heterocyclic Compounds.
Hamazah AS, et al.
Journal of Chemistry, 2013 null
P Poupin et al.
Canadian journal of microbiology, 45(3), 209-216 (1999-07-17)
Nine bacterial strains that grew on morpholine and pyrrolidine as sole carbon, nitrogen, and energy sources were isolated from three different environments with no known morpholine contamination. One of these strains could also degrade piperidine. These bacteria were identified as
Ryozo Shibuya et al.
Angewandte Chemie (International ed. in English), 53(17), 4377-4381 (2014-03-08)
A dual platinum- and pyrrolidine-catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side
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