303143
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
202-468-3
MDL number:
Assay:
99%
Form:
crystals
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
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
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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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