Skip to Content
Merck
All Photos(1)

Documents

364037

Sigma-Aldrich

α-Hydroxy-γ-butyrolactone

technical grade

Synonym(s):

4,5-Dihydro-3-hydroxy-2(3H)-furanone

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C4H6O3
CAS Number:
19444-84-9
Molecular Weight:
102.09
Beilstein:
80587
MDL number:
MFCD00134268
UNSPSC Code:
12352100
PubChem Substance ID:
24862411
NACRES:
NA.22

grade

technical grade

form

viscous liquid

refractive index

n20/D 1.468 (lit.)

bp

133 °C/10 mmHg (lit.)

density

1.309 g/mL at 25 °C (lit.)

SMILES string

OC1CCOC1=O

InChI

1S/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2

InChI key

FWIBCWKHNZBDLS-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

α-Hydroxy-γ-butyrolactone is a 5-membered cyclic ester. It was obtained via tin-conversion of biomass-derived 1,3-dihydroxyacetone (DHA) and formaldehyde.

Application

α-Hydroxy-γ-butyrolactone may be employed as starting reagent in the synthesis of series of seco-pseudonucleoside synthons via aminolysis. It may be employed as starting reagent in the synthesis of enantiomerically pure orthogonally protected δ-azaproline, via Mitsunobu reaction.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Efficient synthesis of enantiomerically pure (S)-d-azaproline starting from (R)-a-hydroxy-?-butyrolactone via the Mitsunobu reaction.
Voss E, et al.
Tetrahedron Asymmetry, 20(15), 1809-1812 (2009)
Sho Yamaguchi et al.
Chemical communications (Cambridge, England), 50(35), 4600-4602 (2014-03-29)
The direct conversion of biomass-derived 1,3-dihydroxyacetone (DHA) and formaldehyde to α-hydroxy-γ-butyrolactone (HBL) was achieved through the use of tin(iv) chloride and a small amount of water and the yield reached up to 70%. The reaction mechanism was also investigated by
Natalia N Dioubankova et al.
Organic letters, 4(26), 4607-4610 (2002-12-20)
[reaction: see text] Two series of seco-pseudonucleoside synthons were synthesized from (R)-(+)-alpha-hydroxy-gamma-butyrolactone and (R)-(-)-pantolactone by aminolysis, side-chain protection, dimethoxytritylation, and phosphitylation or solid-phase attachment. The phosphoramidites and solid supports were used in automated DNA synthesis to prepare oligonucleotides modified with

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service