6713-72-0

Basic information

• Product Name: 3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione
• Synonyms: 3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione;Tetramethylglycolide;Einecs 229-767-1;1,4-Dioxane-2,5-dione, 3,3,6,6-tetraMethyl-
• CAS NO: 6713-72-0
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.17848
• EINECS: 229-767-1
• Mol File: 6713-72-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 271.4°C at 760 mmHg
• Flash Point: 135.1°C
• Appearance: /
• Density: 1.087g/cm³
• Vapor Pressure: 0.00645mmHg at 25°C
• Refractive Index: 1.425
• CAS DataBase Reference: 3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione(6713-72-0)
• EPA Substance Registry System: 3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione(6713-72-0)

Safety Data

• Hazardous Substances Data: 6713-72-0(Hazardous Substances Data)

Usage

General Description

3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione, also known as Meldrum's acid, is a chemical compound with the molecular formula C8H12O4. It is a stable, white, crystalline solid that is commonly used as a reagent in organic synthesis. Meldrum's acid is a versatile building block in organic chemistry, and it is often used to synthesize pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and reactivity make it an important tool for creating a variety of chemical compounds. Meldrum's acid is also used as a component in certain polymer and resin formulations. Despite its utility, Meldrum's acid should be handled with care, as it is a potential irritant to the skin and eyes and may be harmful if ingested or inhaled.

InChI:InChI=1/C8H12O4/c1-7(2)5(9)12-8(3,4)6(10)11-7/h1-4H3

Upstream product

• 594-61-6 2-methyllactic acid 
• 13027-88-8 2-hydroxyisobutyramide 
• 2110-78-3 methyl 2-hydroxy-2-methylpropionate 
• 4560-54-7 2,2,5,5-Tetramethyl-1,3-dioxolane-4-one 
• 79-39-0 Methacrylamide 
• 79-41-4 poly(methacrylic acid) 

Downstream Products

• 80-62-6 methacrylic acid methyl ester 
• 79-41-4 poly(methacrylic acid) 
• 594-61-6 2-methyllactic acid 

Relevant articles and documents

SYNTHESIS OF 3,3,6,6-TETRAMETHYL-1,4-DIOXANE-2,5-DIONE

Conditions for the preparation of 3,3,6,6-tetramethyl-1,4-dioxane-2,5-dione by condensation of 2-hydroxy-2-methylpropanoic acid in the presence of p-toluenesulfonic acid were found.It is shown that the lactide obtained is readily hydrolyzed to 2-(2-hydroxy-2-methylpropanoyloxy)-2-methylpropanoic acid.

A simple synthetic route for the preparation of tetramethylglycolide from lactic acid

Poly(tetramethylglycolide), a chemical recyclable polymer, is currently attracting a lot of interest as a substitute for poly(Llactic acid). We report here a simple and convenient route for the synthesis of tetramethylglycolide (TMG) from lactic acid. This method involves three steps: (1) one-step protection of lactic acid by cyclic acetalization employing acetone; (2) -methylation of the obtained 2,2,5-trimethyl-1,3-dioxolan-4-one; and (3) one-pot synthesis of TMG including the hydrolysis of 2,2,5,5-tetramethyl- 1,3-dioxolan-4-one. We found significant advantages of the incorporation of existing reactions in the synthesis of TMG.

Racemization-free monomer: A-hydroxyisobutyric acid from bio-based lactic acid

In order to solve the important problem of the racemization of poly(L-lactic acid), a high yield of racemization-free monomer: a-hydroxyisobutyric acid (HIBA) was synthesized from biobased lactic acid by methylation using specific bases with bulky side groups. Obtained HIBA can be converted into poly(tetramethylglycolide), which is racemization-free and has higher melting and glass transition points than poly(L-lactic acid).