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186511

Sigma-Aldrich

(S)-(+)-2-Pyrrolidinemethanol

97%

Synonyme(s) :

(S)-(+)-2-(Hydroxymethyl)pyrrolidine, L-Prolinol

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About This Item

Formule empirique (notation de Hill):
C5H11NO
Numéro CAS:
23356-96-9
Poids moléculaire :
101.15
Numéro Beilstein :
79843
Numéro CE :
245-605-2
Numéro MDL:
MFCD00005255
Code UNSPSC :
12352005
ID de substance PubChem :
24851225
Nomenclature NACRES :
NA.22

Pureté

97%

Activité optique

[α]20/D +31°, c = 1 in toluene

Indice de réfraction

n20/D 1.4853 (lit.)

Point d'ébullition

74-76 °C/2 mmHg (lit.)

Densité

1.025 g/mL at 25 °C (lit.)

Chaîne SMILES 

OC[C@@H]1CCCN1

InChI

1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m0/s1

Clé InChI

HVVNJUAVDAZWCB-YFKPBYRVSA-N

Catégories apparentées

Description générale

(S)-(+)-2-Pyrrolidinemethanol, also known as (S)-(+)-prolinol is a chiral building block that is used for the synthesis of chiral organic compounds. It is also used as a chiral auxiliary in asymmetric synthesis and a chiral ligand in asymmetric catalysis.

Application

(S)-(+)-2-Pyrrolidinemethanol can be used as a starting material for the synthesis of (S)-α, α-diaryl-2-pyrrolidinemethanols. It plays an important role in this synthesis by providing chirality to the final product.

Pictogrammes

CorrosionExclamation mark
GHS05,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H318,H335

Classification des risques

Acute Tox. 4 Oral - Eye Dam. 1 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

186.8 °F - closed cup

Point d'éclair (°C)

86 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Sigma-Aldrich

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The photochirogenesis of 2-anthracenecarboxylic acid (AC) complexed to a hydrogen-bonding template (TKS159) was investigated to obtain mechanistic information on how chirogenesis is achieved for the dimerization of AC. Complexation of AC to TKS159 leads to the shielding of one of
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Journal of medical toxicology : official journal of the American College of Medical Toxicology, 4(3), 167-169 (2008-09-30)
Many countries have specific legislation, such as the Controlled Substances Act (1970) in the United States and the Misuse of Drugs Act (1971) in the United Kingdom to control recreational drugs. There is a growing market and supply of "novel"
Patrick Bolze et al.
Organic letters, 10(17), 3753-3756 (2008-07-29)
A simple organocatalytic approach to highly attractive chiral building blocks is presented. By the reaction of beta-ketoesters with alpha,beta-unsaturated aldehydes using a chiral TMS-protected prolinol as the catalyst, optically active 5-(trialkylsilyl)cyclohex-2-enones are formed in good yields and with 98-99% ee.
Magnus Rueping et al.
Organic & biomolecular chemistry, 10(30), 6201-6210 (2012-05-16)
A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of l-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael
Tatsuya Urushima et al.
Organic letters, 12(13), 2966-2969 (2010-06-10)
Diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of commercially available polymeric ethyl glyoxylate, affording gamma-ethoxycarbonyl-beta-hydroxy aldehydes, versatile synthetic intermediates, in good yield with excellent enantioselectivity.
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