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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

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

Signal Word

Warning

Hazard Statements

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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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
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)
Fabio Marchetti et al.
Dalton transactions (Cambridge, England : 2003), 42(8), 2792-2802 (2012-09-11)
A series of group 4 metal tetracarbamates M(O(2)CNR(2))(4) (M = Ti, R = Et, 1a; M = Zr, R = Et, 1b; (i)Pr, 1c; M = Hf, R = Et, 1d; R = (i)Pr, 1e) were studied as catalytic precursors
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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