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Merck

303143

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

99%

Synonyme(s) :

DL-Lactide, rac-Lactide, Lactide

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A propos de cet article

Formule empirique (notation de Hill) :
C6H8O4
Numéro CAS:
Poids moléculaire :
144.13
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
202-468-3
MDL number:
Assay:
99%
Form:
crystals
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InChI key

JJTUDXZGHPGLLC-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

99%

form

crystals

bp

142 °C/8 mmHg (lit.)

mp

116-119 °C

functional group

ester

storage temp.

2-8°C

Quality Level

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Consulter la Bibliothèque de documents

Tetrahedron Letters, 47, 6517-6517 (2006)
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
Kimberly M Osten et al.
Dalton transactions (Cambridge, England : 2003), 41(26), 8123-8134 (2012-04-07)
Functionalized diaminophenols, H(N(R1R2)N(R3)O), were investigated as ligands for indium catalysts in the ring-opening polymerization of racemic lactide. Precursor complexes (N(Me2)N(Me)O)InCl(2) (1), (N(Pr2)NO)InCl(2) (2), and (N(Mes)NO)InCl(2) (3) were synthesized and fully characterized by (1)H and (13)C NMR spectroscopy, elemental analysis, and
Anne Marit de Groot et al.
Journal of controlled release : official journal of the Controlled Release Society, 266, 27-35 (2017-09-18)
The skin is an attractive organ for immunization due to the presence of a large number of epidermal and dermal antigen-presenting cells. Hollow microneedles allow for precise and non-invasive intradermal delivery of vaccines. In this study, ovalbumin (OVA)-loaded poly(lactic-co-glycolic acid)
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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