P73803
Pyrrolidine
99%
Synonym(s):
Tetrahydropyrrole, Tetramethyleneimine
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About This Item
Empirical Formula (Hill Notation):
C4H9N
CAS Number:
Molecular Weight:
71.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
204-648-7
Beilstein/REAXYS Number:
102395
MDL number:
Assay:
99%
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
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:
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.
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signalword
Danger
hcodes
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
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
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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)
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)