869491-43-0

Basic information

• Product Name: 1,3-Dioxan-2-one, 5,5-dimethoxy-
• CAS NO: 869491-43-0
• Molecular Formula: C6H10O5
• Molecular Weight: 162.142
• Mol File: 869491-43-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3-Dioxan-2-one, 5,5-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxan-2-one, 5,5-dimethoxy-(869491-43-0)
• EPA Substance Registry System: 1,3-Dioxan-2-one, 5,5-dimethoxy-(869491-43-0)

Safety Data

• Hazardous Substances Data: 869491-43-0(Hazardous Substances Data)

Usage

General Description

1,3-Dioxan-2-one, 5,5-dimethoxy, also known as dimethoxyglycolide, is a chemical compound with the molecular formula C6H10O4. It is a cyclic organic compound derived from the reaction of glycolic acid with formaldehyde. 1,3-Dioxan-2-one, 5,5-dimethoxy- is used in the synthesis of biodegradable polymers such as poly(glycolic acid) and polylactic acid, which have applications in the medical and pharmaceutical industries. Additionally, dimethoxyglycolide is also used as a solvent and reagent in organic synthesis. It is a colorless, flammable liquid with a fruity odor and is considered to be potentially harmful if inhaled, ingested, or in contact with skin.

Upstream product

• 124-38-9 carbon dioxide 
• 153214-82-5 2,2-dimethoxypropane-1,3-diol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 541-41-3 chloroformic acid ethyl ester 
• 201230-82-2 carbon monoxide 

Relevant articles and documents

In-chain functionalization through the combination of ring opening copolymerization and oxime “Click” reaction towards X-ray opaque polylactide copolymers

X-ray imaging functionalization of biodegradable polyesters is a great demand and challenge in biomedical applications. In this work, a strategy of in-chain functionalization through the combination of ring opening copolymerization and oxime “Click” postfunctionalization was developed towards X-ray opaque polylactide copolymers. A functionalized cyclic carbonate was first synthesized and used as comonomer of polylactide copolymers, which were subjected to postfunctionalization of oxime “Click” reaction towards iodinated polylactide copolymers. The chemical structure and physical properties of the target products were traced and confirmed. In vitro cytotoxicity evaluation with 3T3-Swiss albino by Alamar blue demonstrated a low cytotoxicity. The X-ray radiopacity was analyzed by Micro-CT and quantified by Hounsfield Units value, which could be tailorable by the feedstock. It is a promising X-ray visible implantable biomaterial in biomedical applications.

Semicrystalline dihydroxyacetone copolymers derived from glycerol

The ring-opening polymerization of glycerol-derived six-membered cyclic dimethylacetal dihydroxyacetone carbonate (MeO2DHAC) have been studied both in solution and bulk conditions with organic catalysts. The guanidine 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) was the most active catalyst in solution, whereas the thiourea/sparteine catalytic system displayed the most predictable kinetics. Ring-opening polymerization of MeO2DHAC or copolymerization with ε-caprolactone (CL) in the melt occurred readily with TBD as catalyst to afford random copolymers. Acetal deprotection afforded the polycarbonate poly(dihydroxyactone carbonate) (p(DHAC)) or poly(carbonate ester) copolymers p(DHAC-r-CL). The polycarbonate p(DHAC) is a high-melting thermoplastic with a melting point of 246 °C. The p(DHAC-r-CL) copolymers all displayed semicrystalline behavior as evidenced by DSC and WAXS analysis with Tg and Tm changing as a function of comonomer composition. These new materials could have potential use in biomedical applications or as biomass-derived thermoplastics.

Palladium-catalyzed carbonylation of diols to cyclic carbonates

The catalytic alkoxycarbonylation of 1,2-diols by (neocuproine) palladium(II) acetate (neocuproine=2,9-dimethyl-1,10-phenanthroline) or palladium(II) acetate/(-)-sparteine using N-chlorosuccinimide as the oxidant affords cyclic carbonates. The oxidative carbonylation of diols proceeds under mild conditions, requiring only 1 atm of carbon monoxide, and produces cyclic carbonates in moderate to good yields. Both 1,2- and 1,3-diols can be carbonylated using (neocuproine)Pd(OAc)2 and sodium dichloroisocyanuric acid, which serves as a competent oxidant and base for this system, to yield 5- and 6-membered cyclic carbonates. Copyright