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Merck
CN

186511

(S)-(+)-2-Pyrrolidinemethanol

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C5H11NO
CAS Number:
23356-96-9
Molecular Weight:
101.15
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24851225
EC Number:
245-605-2
Beilstein/REAXYS Number:
79843
MDL number:
MFCD00005255

Key Documents

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Product Name

(S)-(+)-2-Pyrrolidinemethanol, 97%

InChI key

HVVNJUAVDAZWCB-YFKPBYRVSA-N

InChI

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

SMILES string

OC[C@@H]1CCCN1

assay

97%

optical activity

[α]20/D +31°, c = 1 in toluene

refractive index

n20/D 1.4853 (lit.)

bp

74-76 °C/2 mmHg (lit.)

density

1.025 g/mL at 25 °C (lit.)

functional group

hydroxyl

Quality Level

100

Related Categories

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.

General description

(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.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

186.8 °F - closed cup

flash_point_c

86 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ1480
MKCX0408
MKCM4662
MKCL1128
MKCC4782

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Janine Cossy
Chemical record (New York, N.Y.), 5(2), 70-80 (2005-04-13)
The synthesis of optically active substituted piperidines has been achieved by using four different methodologies. The first one is an intramolecular nucleophilic displacement of activated alcohol moieties that was used to build up the piperidine ring of (-)-prosophylline and (-)-slaframine
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
Satnam Lidder et al.
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"
Yuko Kawanami et al.
The Journal of organic chemistry, 74(20), 7908-7921 (2009-09-19)
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
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.
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