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303143

Sigma-Aldrich

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

99%

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Synonym(s):
DL-Lactide, rac-Lactide, Lactide
Empirical Formula (Hill Notation):
C6H8O4
CAS Number:
95-96-5
Molecular Weight:
144.13
EC Number:
202-468-3
MDL number:
MFCD00011685
PubChem Substance ID:
24858300
NACRES:
NA.22

Quality Level

200

Assay

99%

form

crystals

bp

142 °C/8 mmHg (lit.)

mp

116-119 °C

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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1 of 4

This Item
851450900890367044
3,6-Dimethyl-1,4-dioxane-2,5-dione 99%

Sigma-Aldrich

303143

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

D-(+)-Glucuronic acid γ-lactone ≥99%

Sigma-Aldrich

851450

D-(+)-Glucuronic acid γ-lactone

3-Methyl-6-propargyl-1,4-dioxane-2,5-dione ≥95%

Sigma-Aldrich

900890

3-Methyl-6-propargyl-1,4-dioxane-2,5-dione

(3S)-cis-3,6-Dimethyl-1,4-dioxane-2,5-dione 98%

Sigma-Aldrich

367044

(3S)-cis-3,6-Dimethyl-1,4-dioxane-2,5-dione

form

crystals

form

powder

form

solid

form

crystals

bp

142 °C/8 mmHg (lit.)

bp

-

bp

-

bp

-

mp

116-119 °C

mp

172-175 °C (lit.)

mp

-

mp

92-94 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

−20°C

storage temp.

2-8°C

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
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Lu Qin et al.
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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
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