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83240

Sigma-Aldrich

Pyrrolidine

≥99.0%

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Synonym(s):
Tetrahydropyrrole, Tetramethyleneimine
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:
329769283
NACRES:
NA.22

vapor density

2.45 (vs air)

Quality Level

100

vapor pressure

128 mmHg ( 39 °C)
49 mmHg ( 20 °C)

Assay

≥99.0% (GC)
≥99.0%

form

liquid

autoignition temp.

653 °F

expl. lim.

10.6 %

impurities

≤0.5% water

refractive index

n20/D 1.443 (lit.)
n20/D 1.443

density

0.852 g/mL at 25 °C (lit.)

cation traces

Al: ≤0.5 mg/kg
Ba: ≤0.1 mg/kg
Bi: ≤0.1 mg/kg
Ca: ≤0.5 mg/kg
Cd: ≤0.05 mg/kg
Co: ≤0.02 mg/kg
Cr: ≤0.02 mg/kg
Cu: ≤0.02 mg/kg
Fe: ≤0.4 mg/kg
K: ≤0.5 mg/kg
Li: ≤0.1 mg/kg
Mg: ≤0.1 mg/kg
Mn: ≤0.02 mg/kg
Mo: ≤0.1 mg/kg
Na: ≤0.5 mg/kg
Ni: ≤0.02 mg/kg
Pb: ≤0.1 mg/kg
Sr: ≤0.1 mg/kg
Zn: ≤0.1 mg/kg

SMILES string

C1CCNC1

InChI

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

InChI key

RWRDLPDLKQPQOW-UHFFFAOYSA-N

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Application

Pyrrolidine can be used as:
  • A base for the chemoselective reduction of ketones to alcohol in the presence of decaborane and cerium(III) chloride heptahydrate in methanol.
  • A reactant with benzaldehyde and β-naphthol for the synthesis of betti base using non-ionic surfactant (Triton X-100) as a catalyst.
  • A catalyst in the synthesis of aldimines from aldehydes and primary amines.
  • A modifier for aluminum hydride reagent, which is used as a selective reducing agent to transform N-benzyl-4-ethoxycarbonylpiperidine into N-benzyl-4-formylpiperidine.
  • As a solvent/base in palladium-catalyzed Sonagashira coupling reactions.

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

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Reduction of ketones to alcohols using a decaborane/pyrrolidine/cerium (III) chloride system in methanol
Bae JW, et al.
Tetrahedron Letters, 42(11), 2137-2139 (2001)
Large scale synthesis of N-benzyl-4-formylpiperidine through partial reduction of esters using aluminum hydride reagents modified with pyrrolidine
Abe T, et al.
Tetrahedron, 57(14), 2701-2710 (2001)
A general aminocatalytic method for the synthesis of aldimines
Morales S, et al.
Journal of the American Chemical Society, 136(3), 1082-1089 (2014)
Non-ionic surfactant catalyzed synthesis of Betti base in water
Kumar A, et al.
Tetrahedron Letters, 51(12), 1582-1584 (2010)
Rapid, easy copper-free Sonogashira couplings using aryl iodides and activated aryl bromides
Leadbeater NE and Tominack BJ
Tetrahedron Letters, 44(48), 8653-8656 (2003)
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