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Merck
CN

83241

Pyrrolidine

puriss. plus, ≥99.5% (GC)

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
EC Number:
204-648-7
UNSPSC Code:
12352100
MDL number:
MFCD00005249
Beilstein/REAXYS Number:
102395

Key Documents

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InChI

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

InChI key

RWRDLPDLKQPQOW-UHFFFAOYSA-N

SMILES string

C1CCNC1

vapor density

2.45 (vs air)

vapor pressure

128 mmHg ( 39 °C), 49 mmHg ( 20 °C)

grade

puriss. plus

assay

≥99.5% (GC)

autoignition temp.

653 °F

expl. lim.

10.6 %

impurities

≤0.5% water

density

0.852 g/mL at 25 °C (lit.)

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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

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

Regulatory Information

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Joseph T Paletta et al.
Organic letters, 14(20), 5322-5325 (2012-10-12)
A series of sterically shielded pyrrolidine nitroxides were synthesized, and their reduction by ascorbate (vitamin C) indicate that nitroxide 3, a tetraethyl derivative of 3-carboxy-PROXYL, is reduced at the slowest rate among known nitroxides, i.e., at a 60-fold slower rate
Adele Faulkner et al.
Chemical communications (Cambridge, England), 49(15), 1521-1523 (2013-01-17)
We report efficient Pd-catalyzed cyclizations of oxime esters with 1,1-disubstituted alkenes as the basis of a general entry to α,α-disubstituted pyrrolidine derivatives. We also demonstrate that catalytic asymmetric variants of this chemistry are feasible by employing a suitable chiral ligand.
Edwige Lorthiois et al.
Journal of medicinal chemistry, 56(6), 2207-2217 (2013-02-22)
The small-molecule trans-3,4-disubstituted pyrrolidine 6 was identified from in silico three-dimensional (3D) pharmacophore searches based on known X-ray structures of renin-inhibitor complexes and demonstrated to be a weakly active inhibitor of the human enzyme. The unexpected binding mode of the
Y Arun et al.
Bioorganic & medicinal chemistry letters, 23(6), 1839-1845 (2013-02-12)
Novel dispirooxindole-pyrrolidine derivatives have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine with the dipolarophile 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindolin-3-ylidene)propanenitrile, and also spiro compound of acenaphthenequinone obtained by the same optimized reaction condition. Synthesized compounds were evaluated for
Hiroaki Chiba et al.
Angewandte Chemie (International ed. in English), 51(36), 9169-9172 (2012-08-15)
In control: The novel and enantioselective total synthesis of (-)-quinocarcin includes the highly stereoselective preparation of the 2,5-cis-pyrrolidine by intramolecular amination, a selective substrate-controlled 6-endo-dig intramolecular alkyne hydroamination with a cationic Au(I) catalyst, and Lewis-acid-mediated ring-opening/halogenation sequence.
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