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P73803

Sigma-Aldrich

Pyrrolidine

99%

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Synonym(s):
Tetrahydropyrrole, Tetramethyleneimine
Empirical Formula (Hill Notation):
C4H9N
CAS Number:
Molecular Weight:
71.12
Beilstein:
102395
EC Number:
MDL number:
PubChem Substance ID:

vapor density

2.45 (vs air)

Quality Level

vapor pressure

128 mmHg ( 39 °C)
49 mmHg ( 20 °C)

Assay

99%

autoignition temp.

653 °F

expl. lim.

10.6 %

refractive index

n20/D 1.443 (lit.)

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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1 of 4

This Item
W352316832408.07494
Pyrrolidine 99%

Sigma-Aldrich

P73803

Pyrrolidine

Pyrrolidine FG

Sigma-Aldrich

W352316

Pyrrolidine

Pyrrolidine ≥99.0%

Sigma-Aldrich

83240

Pyrrolidine

Pyrrolidine for synthesis

Sigma-Aldrich

8.07494

Pyrrolidine

refractive index

n20/D 1.443 (lit.)

refractive index

n20/D 1.443 (lit.)

refractive index

n20/D 1.443 (lit.)

refractive index

-

density

0.852 g/mL at 25 °C (lit.)

density

0.852 g/mL at 25 °C (lit.)

density

0.852 g/mL at 25 °C (lit.)

density

0.86 g/cm3 at 20 °C

Quality Level

200

Quality Level

400

Quality Level

100

Quality Level

200

vapor density

2.45 (vs air)

vapor density

2.45 (vs air)

vapor density

2.45 (vs air)

vapor density

-

vapor pressure

128 mmHg ( 39 °C)

vapor pressure

128 mmHg ( 39 °C), 49 mmHg ( 20 °C)

vapor pressure

128 mmHg ( 39 °C), 49 mmHg ( 20 °C)

vapor pressure

65 hPa ( 20 °C)

General description

Pyrrolidine is a heterocyclic building block used in organic synthesis and a scaffold for biologically active compounds.

Application

Pyrrolidine has been used for the synthesis of N-benzoyl pyrrolidine from benzaldehyde via oxidative amination. It may be used as a catalyst for the synthesis of N-sulfinyl aldimines from carbonyl compounds and sulfonamides.
Pyrrolidine can also be used to synthesize:
  • Taddol-pyrrolidine phosphoramidite, a ligand for rhodium-catalyzed [2+2+2] cycloaddition of pentenyl isocyanate and 4- ethynylanisole.
  • H,4 PyrrolidineQuin-BAM (′PBAM′), a selective catalyst for the aza-Henry addition of nitroalkanes to aryl aldimines.{88]
  • 1,2,3,3a,4,9-Hexahydropyrrolo[2,1-b]quinazoline by reacting with o-aminobenzaldehyde.

Signal Word

Danger

Hazard Statements

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)

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25G
Pack Size/Quantity

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705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

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Enantioselective Rhodium-Catalyzed [2+2+2] Cycloaddition of Pentenyl Isocyanate and 4-Ethynylanisole: Preparation and Use of Taddol-pyrrolidine Phosphoramidite
Oberg KM, et al.
Organic Syntheses, 91, 150-150 (2014)
Metal?Free One?Pot Oxidative Amination of Aromatic Aldehydes: Conversion of Benzaldehyde to N?Benzoyl Pyrrolidine.
Ekoue?Kovi K & Wolf C
Organic Syntheses, 1-7 (2010)
o-Aminobenzaldehyde, Redox-Neutral Aminal Formation and Synthesis of Deoxyvasicinone
Zhang C, et al.
Organic Syntheses, 89, 274-274 (2012)
Preparation of N-Sulfinyl Aldimines using Pyrrolidine as Catalyst via Iminium Ion Activation
Morales S, et al.
Organic Syntheses, 94, 346-346 (2017)
Pyrrolidine in drug discovery: a versatile scaffold for novel biologically active compounds
Li Petri G, et al.
Topics in Current Chemistry, 379, 1-46 (2021)

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