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303143

Sigma-Aldrich

3,6-Dimethyl-1,4-dioxane-2,5-dione

99%

Synonym(s):

DL-Lactide, rac-Lactide, Lactide

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About This Item

Empirical Formula (Hill Notation):
C6H8O4
CAS Number:
Molecular Weight:
144.13
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

crystals

bp

142 °C/8 mmHg (lit.)

mp

116-119 °C

functional group

ester

storage temp.

2-8°C

SMILES string

CC1OC(=O)C(C)OC1=O

InChI

1S/C6H8O4/c1-3-5(7)10-4(2)6(8)9-3/h3-4H,1-2H3

InChI key

JJTUDXZGHPGLLC-UHFFFAOYSA-N

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General description

3,6-Dimethyl-1,4-dioxane-2,5-dione (or rac-lactide), is the 50:50 racemic mixture of D- and L-Lactide. Rac-lactide is a lactone derived from lactic acid that has attracted great interest in academia and commercial applications, as it is derived from abundant renewable resources. Rac-lactide can be ready polymerized via ring-opening polymerization, using a variety of metal or organocatalysts, yielding poly(D,L-lactide). While the resulting polymer is generally amorphous, the use of stereospecific catalysts can lead to heterotactic PLA, which exhibits some degree of crystallinity.

Application

3,6-Dimethyl-1,4-dioxane-2,5-dione can be used as a reactant:
  • To synthesize multi-block copolymers of polylactide and polycarbonate.
  • In the aluminum-catalyzed polymerization of propene oxide, lactide, and phthalic anhydride to produce multi-block polyesters.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Vibrational Optical Activity of (3 S, 6 S)-3, 6-Dimethyl-1, 4-dioxane-2, 5-dione.
Tam CN, et al.
Journal of the American Chemical Society, 118(42), 10285-10293 (1996)
Lu Qin et al.
Dalton transactions (Cambridge, England : 2003), 48(32), 12315-12325 (2019-07-26)
In this paper we report a series of Al(iii) complexes supported by N,O-bidentate β-pyrazyl functionalized enolate ligands HL1-HL5 (L = (6-Me-2,5-C4H2N2)-CH[double bond, length as m-dash]C(R)-O-), (R = tBu, Ph, p-tolyl, p-OMePh, o-tolyl) and their exploitation for the ring-opening polymerization of
Tetrahedron Letters, 47, 6517-6517 (2006)
Feiyang Li et al.
ACS omega, 5(31), 19796-19804 (2020-08-18)
Bone regeneration has attracted extensive attention in the field of regenerative medicine. The influence of biomaterial on the extracellular environment is important for regulating the biological functions of cells for tissue regeneration. Among the various influencing factors, we had previously
Clare Bakewell et al.
Journal of the American Chemical Society, 134(51), 20577-20580 (2012-12-13)
Highly active yttrium phosphasalen initiators for the stereocontrolled ring-opening polymerization of rac-lactide are reported. The initiators are coordinated by a new class of ancillary ligand: an iminophosphorane derivative of the popular "salen" ligand, termed "phosphasalen". Changing the phosphasalen structure enables

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