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422886

Sigma-Aldrich

(S)-(+)-2-(Aminomethyl)pyrrolidine

97%

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About This Item

Empirical Formula (Hill Notation):
C5H12N2
CAS Number:
Molecular Weight:
100.16
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

liquid

optical activity

[α]20/D +20°, c = 1 in chloroform

refractive index

n20/D 1.482 (lit.)

bp

65 °C/11 mmHg (lit.)

density

0.933 g/mL at 25 °C (lit.)

SMILES string

NC[C@@H]1CCCN1

InChI

1S/C5H12N2/c6-4-5-2-1-3-7-5/h5,7H,1-4,6H2/t5-/m0/s1

InChI key

AUKXFNABVHIUAC-YFKPBYRVSA-N

General description

(S)-(+)-2-(Aminomethyl)pyrrolidine is a chiral vicinal diamine.

Application

(S)-(+)-2-(Aminomethyl)pyrrolidine can be used as an organocatalyst:
  • For the asymmetric transformation of (S)-alanine.
  • In the asymmetric α-fluorination of linear and branched aldehydes using N-fluorobenzenesulfonamide as the fluorinating agent.

It can also be used as a reactant to prepare Schiff base metal complexes with pyrrolidine fragment as a ligand in asymmetric synthesis.
Used in the synthesis of compounds with antitumor activity.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Dioxovanadium (V) complexes of Schiff bases derived from S-(+)-2-(aminomethyl) pyrrolidine and aromatic o-hydroxycarbonyl compounds: Synthesis, characterization and structure
Kwiatkowski E, et al.
Polyhedron, 25(15), 2809-2814 (2006)
Direct asymmetric α-fluorination of aldehydes
Steiner DD, et al.
Angewandte Chemie (International ed. in English), 44(24), 3706-3710 (2005)
Asymmetric Transformation of Alanine via Optically Labile Imidazolines
Shibata S, et al.
Bulletin of the Chemical Society of Japan, 52(10), 2938-2941 (1979)
K Morikawa et al.
Journal of pharmaceutical sciences, 80(9), 837-842 (1991-09-01)
The optical isomers of 2-aminomethylpyrrolidine(1,1-cyclobutane- dicarboxylato)platinum(II) (DWA2114, 1), which has potent antitumor activity against various tumors, were synthesized. They were examined for antitumor activity against Colon 26 carcinoma in a sc-iv system, and changes in urinary protein and sugar levels

Articles

Chiral vicinal diamines are of tremendous interest to the synthetic chemist as they are found in many chiral catalysts and pharmaceuticals.

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