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Sigma-Aldrich

α-Hydroxy-γ-butyrolactone

technical grade

Synonym(s):

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

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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.)

functional group

ester
hydroxyl

SMILES string

OC1CCOC1=O

InChI

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

InChI key

FWIBCWKHNZBDLS-UHFFFAOYSA-N

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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

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Certificates of Analysis (COA)

Lot/Batch Number
0000236276
0000245385
0000229710
MKBV6889V
MKBR1389V

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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
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)
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

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