# 1,2-Dioxin

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For other dioxin compounds, see [dioxin](/source/Dioxin).

1,2-Dioxin Skeletal formula of 1,2-dioxin Names Preferred IUPAC name 1,2-Dioxine Systematic IUPAC name 1,2-Dioxacyclohexa-3,5-diene Identifiers CAS Number 289-87-2 N 3D model (JSmol) Interactive image ChemSpider 10606250 Y PubChem CID 15559065 UNII R8H79L3J69 Y CompTox Dashboard (EPA) DTXSID90574144 InChI InChI=1S/C4H4O2/c1-2-4-6-5-3-1/h1-4H Y Key: VCZQYTJRWNRPHF-UHFFFAOYSA-N Y InChI=1/C4H4O2/c1-2-4-6-5-3-1/h1-4H Key: VCZQYTJRWNRPHF-UHFFFAOYAH SMILES O1OC=CC=C1 Properties Chemical formula C4H4O2 Molar mass 84.074 g·mol−1 Related compounds Related compounds Dibenzodioxin 1,4-Dioxin Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

**1,2-Dioxin** is a [heterocyclic](/source/Heterocyclic_compound), [organic](/source/Organic_compound), [antiaromatic](/source/Antiaromaticity)[1] [compound](/source/Chemical_compound) with the [chemical formula](/source/Chemical_formula) C4H4O2. It is an [isomeric](/source/Isomer) form of [1,4-dioxin](/source/1%2C4-Dioxin) (or *p*-dioxin).

- 1,2-Dioxin (left) and 1,4-dioxin (right)

Due to its [peroxide](/source/Peroxide)-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Calculations suggest that it would [isomerize](/source/Isomerize) rapidly into but-2-enedial.[2] Even [substituted](/source/Substitution_reaction) [derivatives](/source/Derivative_(chemistry)), such as 1,4-diphenyl-2,3-benzodioxin, are very [labile](/source/Labile).[3]

- Structure of the transient 1,4-diphenyl-2,3-benzodioxin

In 1990, 3,6-bis(*p*-tolyl)-1,2-dioxin (**1**) was incorrectly reported as the first stable derivative.[4] It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable [dione](/source/Diketone).[5]

- Dioxin (1) and dione form (2)

## References

1. **[^](#cite_ref-1)** Pelloni, Stefano; Faglioni, Francesco; Lazzeretti, Paolo (2013-09-01). ["Parity violation energies of C4H4X2 molecules for X = O, S, Se, Te and Po"](https://doi.org/10.1080/00268976.2013.794396). *Molecular Physics*. **111** (16–17): 2387–2391. [doi](/source/Doi_(identifier)):[10.1080/00268976.2013.794396](https://doi.org/10.1080%2F00268976.2013.794396). [hdl](/source/Hdl_(identifier)):[11380/942493](https://hdl.handle.net/11380%2F942493). [ISSN](/source/ISSN_(identifier)) [0026-8976](https://search.worldcat.org/issn/0026-8976). [S2CID](/source/S2CID_(identifier)) [100861633](https://api.semanticscholar.org/CorpusID:100861633).

1. **[^](#cite_ref-2)** Matsumoto, M. (2014). ["Product Class 1: 1,2-Dioxins and Benzo- and Dibenzo- Fused Derivatives"](https://books.google.com/books?id=Ah6GAwAAQBAJ&pg=PA13). *Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 16: Six-Membered Hetarenes with Two Identical Heteroatoms*. Georg Thieme Verlag. p. 13. [ISBN](/source/ISBN_(identifier)) [9783131718815](https://en.wikipedia.org/wiki/Special:BookSources/9783131718815). Retrieved 2020-06-12.

1. **[^](#cite_ref-3)** Smith, Jimmie P.; Schrock, Alan K.; Schuster, Gary B. (1982). "Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide". *Journal of the American Chemical Society*. **104** (4): 1041. [doi](/source/Doi_(identifier)):[10.1021/ja00368a021](https://doi.org/10.1021%2Fja00368a021)..

1. **[^](#cite_ref-4)** Shine, Henry J.; Zhao, Da Chuan (1990). "Electron transfer to excited doublet states. Photoirradiation of 10-methylphenothiazine cation radical perchlorate in solutions of phenylacetylene and p-tolylacetylene in acetonitrile". *The Journal of Organic Chemistry*. **55** (13): 4086. [doi](/source/Doi_(identifier)):[10.1021/jo00300a026](https://doi.org/10.1021%2Fjo00300a026)..

1. **[^](#cite_ref-5)** Block, Eric; Shan, Zhixing; Glass, Richard S.; Fabian, Jürgen (2003). "Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study". *The Journal of Organic Chemistry*. **68** (10): 4108–11. [doi](/source/Doi_(identifier)):[10.1021/jo034305i](https://doi.org/10.1021%2Fjo034305i). [PMID](/source/PMID_(identifier)) [12737603](https://pubmed.ncbi.nlm.nih.gov/12737603).

## External links

- [Chemistry portal](https://en.wikipedia.org/wiki/Portal:Chemistry)

- Media related to [1,2-Dioxin](https://commons.wikimedia.org/wiki/Category:1,2-Dioxin) at Wikimedia Commons

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