Skip to Content
MilliporeSigma
All Photos(3)

Documents

P73803

Sigma-Aldrich

Pyrrolidine

99%

Synonym(s):

Tetrahydropyrrole, Tetramethyleneimine

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C4H9N
CAS Number:
123-75-1
Molecular Weight:
71.12
Beilstein/REAXYS Number:
102395
EC Number:
204-648-7
MDL number:
MFCD00005249
UNSPSC Code:
12352100
PubChem Substance ID:
24898844
NACRES:
NA.22

vapor density

2.45 (vs air)

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

37.4 °F - closed cup

flash_point_c

3 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service