1,2-Dioxane

1,2-Dioxane
Names
	Preferred IUPAC name 1,2-Dioxane
	Other names o-Dioxane
Identifiers
CAS Number	5703-46-8;
3D model (JSmol)	Interactive image;
ChemSpider	122188;
PubChem CID	138570;
UNII	DK6UQU3A2W ;
CompTox Dashboard (EPA)	DTXSID50205644 ;
	SMILES C1CCOOC1;
Properties
Chemical formula	C4H8O2
Molar mass	88.106 g·mol−1
Appearance	colorless liquid
Boiling point	116–117 °C (241–243 °F; 389–390 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,2-Dioxane or o-dioxane is an organic compound with the molecular formula (CH₂)₄O₂, classified as a cyclic peroxide. Its synthesis was reported in 1956 by Criegee and Müller, who prepared it by reacting butane-1,4-diol bis(methanesulfonate) with hydrogen peroxide and distilled it as a colorless liquid. Acids and bases decompose it to gamma-hydroxybutyraldehyde.^[1]

Substituted 1,2-dioxanes have also been prepared, and some have been isolated from natural sources.^[2]

^ Criegee, Rudolf; Müller, Gerhard (1956). "1,2-Dioxan". Chem. Ber. 89 (2): 238–240. doi:10.1002/cber.19560890209.
^ Parrish, Jonathan D.; Ischay, Michael A.; Lu, Zhan; Guo, Song; Peters, Noel R.; Yoon, Tehshik P. (2012). "Endoperoxide Synthesis by Photocatalytic Aerobic [2 + 2 + 2] Cycloadditions". Organic Letters. 14 (6): 1640–1643. doi:10.1021/ol300428q. PMC 3306464. PMID 22372647.

[1] Criegee, Rudolf; Müller, Gerhard (1956). "1,2-Dioxan". Chem. Ber. 89 (2): 238–240. doi:10.1002/cber.19560890209.

[2] Parrish, Jonathan D.; Ischay, Michael A.; Lu, Zhan; Guo, Song; Peters, Noel R.; Yoon, Tehshik P. (2012). "Endoperoxide Synthesis by Photocatalytic Aerobic [2 + 2 + 2] Cycloadditions". Organic Letters. 14 (6): 1640–1643. doi:10.1021/ol300428q. PMC 3306464. PMID 22372647.

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