3524-70-7

Basic information

• Product Name: 1,4-dioxane-2,3-dione
• Synonyms: 1,4-Dioxane-2,3-dione
• CAS NO: 3524-70-7
• Molecular Formula: C₄H₄O₄
• Molecular Weight: 116.0722
• Mol File: 3524-70-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 283.3°C at 760 mmHg
• Flash Point: 128.6°C
• Density: 1.423g/cm³
• Vapor Pressure: 0.00318mmHg at 25°C
• Refractive Index: 1.45
• CAS DataBase Reference: 1,4-dioxane-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-dioxane-2,3-dione(3524-70-7)
• EPA Substance Registry System: 1,4-dioxane-2,3-dione(3524-70-7)

Safety Data

• Hazardous Substances Data: 3524-70-7(Hazardous Substances Data)

Usage

General Description

1,4-dioxane-2,3-dione, also known as 1,4-dioxane-2,3-dione-1-oxa-2,3-dioxan-5-one, is a chemical compound with the molecular formula C4H4O5. It is a cyclic diester and a highly reactive compound that is not naturally occurring, but can be synthesized in a laboratory. 1,4-dioxane-2,3-dione is known for its high reactivity and has been used in the synthesis of various pharmaceuticals and biologically active compounds. It can undergo polymerization and is being researched for potential applications in biodegradable polymers and controlled release drug delivery systems. However, 1,4-dioxane-2,3-dione is also considered hazardous and has been classified as a potential mutagen and carcinogen, leading to concerns about its safety and potential environmental impact.

Upstream product

• 79-37-8 oxalyl dichloride 
• 553-90-2 Dimethyl oxalate 
• 107-21-1 ethylene glycol 
• 617-37-8 oxalic acid monoethyl ester 
• 95-92-1 oxalic acid diethyl ester 
• 3590-59-8 2,2-dibutyl[1,3,2]dioxastannolane 

Downstream Products

• 129282-31-1 2-hydroxy-2-benzoyl-1,3-dioxolane 
• 96-49-1 [1,3]-dioxolan-2-one 
• 74-85-1 ethene 
• 15719-64-9 methylammonium carbonate 

Relevant articles and documents

Efficient synthesis and hydrolysis of cyclic oxalate esters of glycols.

Based on the mechanism postulated for the formation of the cyclic carbonates 3 in the reactions of glycols 1 with oxalyl chloride in the presence of triethylamine, we present here three efficient syntheses of the cyclic oxalates 2 of various glycols 1 by controlling the formation of 3: replacement of the base by pyridine markedly diminishes yields of 3 in all reactions, realizing dramatic reversals of the product ratios in the reactions with the (R*,R*)-compounds 1g-i,q,r and pinacol (1k); although considerable amounts of the oxalate polymers are formed in the reactions with some (R*,S*)-glycols, this drawback can be removed by the use of 2,4,6-collidine instead of pyridine; 1,1'-oxalyldiimidazole is useful for the synthesis of two selected cyclic oxalates 2e,f. The cyclic oxalates 2 other than trisubstituted and tetrasubstituted ones were found to be very reactive: kinetic studies on the hydrolysis of 1,4-dioxane-2,3-dione (2a) as well as its mono- and some selected 5,6-disubstituted derivatives 2 have revealed that they undergo hydrolysis 260-1500 times more rapidly than diethyl oxalate (12) in acetate buffer-acetonitrile (pH 5.69) at 25 degrees C. Although the cyclic oxalate 21 from cis-1,2-cyclopentanediol (11) was 1.5 times more reactive than 2a, it has been shown with other substrates that increasing number of the alkyl substituents decreases the rate of hydrolysis. On the contrary, the phenyl group was found to have somewhat accelerative effect.

Formation of cyclic carbonates in the reactions of 1,2-glycols with oxalyl chloride

Oxalyl chloride reacts with a wide range of 1,2-glycols in the presence of triethylamine to produce 1,3-dioxolan-2-ones together with 1,4-dioxane-2,3-diones; the ratio of the products largely depends on the structure of the 1,2-glycol. The formation of the cyclic carbonates may be rationalized in terms of stereoelectronically controlled cleavage of the tetrahedral intermediates.

THE REACTION OF 1,3,2-DIOXASTANNOLANS WITH DIACYL CHLORIDES: DECARBONYLATION IN THE REACTION WITH OXALYL CHLORIDE

2,2-Dibutyl-1,3,2-dioxastannolans react with carbonyl chloride to give the corresponding ethylene carbonates, and with malonyl chloride or succinyl chloride to give the oligomeric malonates or succinates.The reaction of oxalyl chloride, however, depends of the number of methyl substituents carried by the carbon atoms of the ring; with none, ethylene oxalate is essentially the only product, but increasing methylation induces the evolution of carbon monoxide and the formation of the ethylene carbonate until, with four methyl substituents, only the carbonate of pinacol, and no oxalate is formed, providing a striking example of the Thorpe-Ingold effect.The mechanism of this decarbonylation is discussed.