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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

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).
Katsuhiko Moriyama et al.
The Journal of organic chemistry, 77(21), 9846-9851 (2012-10-12)
The intramolecular aminohydroxylation of N-alkenylsulfonamides proceeded under heavy metal-free conditions to give substituted prolinol derivatives in high yields. Oxone activated by catalytic Brønsted acid worked well as an electrophilic oxidant for this reaction.
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
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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