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364037

Sigma-Aldrich

α-Hydroxy-γ-butyrolactone

technical grade

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Synonym(s):
4,5-Dihydro-3-hydroxy-2(3H)-furanone
Empirical Formula (Hill Notation):
C4H6O3
CAS Number:
Molecular Weight:
102.09
Beilstein/REAXYS Number:
80587
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

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

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This Item
226416444286422797
α-Hydroxy-γ-butyrolactone technical grade

364037

α-Hydroxy-γ-butyrolactone

α-Methylene-γ-butyrolactone 97%

226416

α-Methylene-γ-butyrolactone

(S)-β-Hydroxy-γ-butyrolactone 96%

422797

(S)-β-Hydroxy-γ-butyrolactone

density

1.309 g/mL at 25 °C (lit.)

density

1.119 g/mL at 25 °C (lit.)

density

1.309 g/mL at 25 °C (lit.)

density

1.241 g/mL at 25 °C (lit.)

form

viscous liquid

form

liquid

form

liquid

form

-

refractive index

n20/D 1.468 (lit.)

refractive index

n20/D 1.472 (lit.)

refractive index

n20/D 1.467 (lit.)

refractive index

n20/D 1.464 (lit.)

bp

133 °C/10 mmHg (lit.)

bp

86-88 °C/12 mmHg (lit.)

bp

133 °C/10 mmHg (lit.)

bp

98-100 °C/0.3 mmHg (lit.)

grade

technical grade

grade

-

grade

-

grade

-

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


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Customers Also Viewed

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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