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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:
Molecular Weight:
144.13
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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This Item
851450719935746258
vibrant-m

303143

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

vibrant-m

851450

D-(+)-Glucuronic acid γ-lactone

vibrant-m

746258

L-Lactic acid-13C3

assay

99%

assay

≥99%

assay

-

assay

≥98% (CP), ≥98% (Chiral Purity, HPLC)

form

crystals

form

powder

form

amorphous

form

solid

bp

142 °C/8 mmHg (lit.)

bp

-

bp

-

bp

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

−20°C

mp

116-119 °C

mp

172-175 °C (lit.)

mp

-

mp

-

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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Insun Yu et al.
Journal of the American Chemical Society, 134(30), 12758-12773 (2012-07-07)
A family of racemic and enantiopure indium complexes 1-11 bearing bulky chiral diaminoaryloxy ligands, H(NNO(R)), were synthesized and fully characterized. Investigation of both the mono- and the bis-alkoxy-bridged complexes [(NNO(R))InX](2)[μ-Y][μ-OEt] (5, R = (t)Bu, X = Y = Cl; 8
Tetrahedron Letters, 47, 6517-6517 (2006)
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
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Catheter related infections are causing one third of all blood stream infections. The mortality of those infections is very high and the gold standard for catheter related blood stream infections (CR-BSI) is still the removal of the catheter and systemic

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