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186511

Sigma-Aldrich

(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
Beilstein:
79843
EC Number:
245-605-2
MDL number:
MFCD00005255
UNSPSC Code:
12352005
PubChem Substance ID:
24851225
NACRES:
NA.22

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.)

SMILES string

OC[C@@H]1CCCN1

InChI

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

InChI key

HVVNJUAVDAZWCB-YFKPBYRVSA-N

Related Categories

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.

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.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °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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1-Methyl-2-pyrrolidine ethanol 98%

Sigma-Aldrich

139513

1-Methyl-2-pyrrolidine ethanol

Takashi Mino et al.
The Journal of organic chemistry, 70(5), 1937-1940 (2005-02-26)
Chiral diaminophosphines 4 were prepared from (S)-prolinol-derived aminophosphine oxide 5 by bromination with ring expansion followed by amination with ring contraction and reduction, using trichlorosilane. In the presence of 4 as a ligand, palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate
Patrick G McGarraugh et al.
Organic letters, 13(24), 6460-6463 (2011-11-17)
Products of a novel iminium-catalyzed oxa-Michael addition undergo a kinetic resolution by a subsequent enamine-catalyzed intermolecular reaction. This is a rare example of kinetic resolution by enamine catalysis and the first organocascade kinetic resolution. This resolution produces enantioenriched 2,6-cis-tetrahydropyrans and
Ina Mager et al.
Organic letters, 12(7), 1480-1483 (2010-03-06)
A highly efficient approach for the synthesis, application, and recycling of immobilized diarylprolinol silyl ethers was developed. The MeOPEG-supported Jørgensen-Hayashi catalyst provides unchanged reactivity and selectivity as compared to the homogeneous catalyst, as demonstrated for the Michael addition of nitromethane
Weixu Zhai et al.
Bioorganic & medicinal chemistry letters, 18(18), 5083-5086 (2008-08-30)
The discovery and optimization of a novel series of prolinol-derived GHSR agonists is described. This series emerged from a 11,520-member solid-phase library targeting the GPCR protein superfamily, and the rapid optimization of low micromolar hits into single-digit nanomolar leads can
Chuan Wang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(37), 11531-11535 (2012-07-28)
Sulfenylated oxindoles: The first asymmetric sulfenylation of N-Boc-protected oxindoles has been developed to provide products containing a tetrasubstituted stereogenic center in high to excellent yields (86-98 %) and, in most cases, excellent enantioselectivities (up to 96 % ee; see scheme).
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