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324450

Sigma-Aldrich

(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine

96%

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About This Item

Empirical Formula (Hill Notation):
C9H18N2
CAS Number:
51207-66-0
Molecular Weight:
154.25
MDL number:
MFCD00013441
UNSPSC Code:
12352005
PubChem Substance ID:
24859441
NACRES:
NA.22

Assay

96%

optical activity

[α]19/D +7.0°, c = 2.4 in ethanol

refractive index

n20/D 1.4871 (lit.)

bp

99-101 °C/2 mmHg (lit.)

density

0.946 g/mL at 25 °C (lit.)

SMILES string

C1CCN(C1)C[C@@H]2CCCN2

InChI

1S/C9H18N2/c1-2-7-11(6-1)8-9-4-3-5-10-9/h9-10H,1-8H2/t9-/m0/s1

InChI key

YLBWRMSQRFEIEB-VIFPVBQESA-N

Application

(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine can be used as an organocatalyst in the asymmetric synthesis of different optically active organic building blocks via Aldol condensation and Mannich reactions . It is also used as a catalyst to prepare enantioselective Michael adducts by reacting alkylidene malonates with unactivated ketones.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

190.4 °F - closed cup

Flash Point(C)

88 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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(S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine ? an effective catalyst of asymmetric synthesis
VM Tkachuk, et al.
Zhurnal Organichnoi ta Farmatsevtichnoi Khimii, 3-16 (2014)
Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
Betancort JM, et al.
Tetrahedron Letters, 42(27), 4441-4444 (2001)
M Guipponi et al.
Human genetics, 109(6), 569-575 (2002-01-26)
The human TPTE gene encodes a testis-specific protein that contains four potential transmembrane domains and a protein tyrosine phosphatase motif, and shows homology to the tumor suppressor PTEN/MMAC1. Chromosomal mapping revealed multiple copies of the TPTE gene present on the
Tatiana Leiva-Rodríguez et al.
Cell death & disease, 9(6), 626-626 (2018-05-26)
Injured neurons should engage endogenous mechanisms of self-protection to limit neurodegeneration. Enhancing efficacy of these mechanisms or correcting dysfunctional pathways may be a successful strategy for inducing neuroprotection. Spinal motoneurons retrogradely degenerate after proximal axotomy due to mechanical detachment (avulsion)
Shoujiro Ogawa et al.
Biomedical chromatography : BMC, 30(1), 29-34 (2015-01-27)
A simple liquid chromatography/electrospray ionization-tandem mass spectrometry (LC/ESI-MS/MS) method for determination of the eicosapentaenoic acid (EPA) concentration to arachidonic acid (AA) concentration ratio in human saliva has been developed. The EPA/AA ratio in serum or plasma is widely recognized as
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