Diepoxybutane
 | |
| Names | |
|---|---|
| Preferred IUPAC name
2,2′-Bioxirane | |
| Other names
1,1′-Bi[ethylene oxide]; 1,2:3,4-Diepoxybutane; 1,3-Butadiene diepoxide; Bioxirane; Butadiene dioxide; Butane diepoxide; Dioxybutadiene | |
| Identifiers | |
| |
3D model (JSmol) |
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| Abbreviations | DEB |
| 79831 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.014.527 |
| EC Number |
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PubChem CID |
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| UNII |
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| UN number | 3384 3082 |
CompTox Dashboard (EPA) |
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| Properties | |
| C4H6O2 | |
| Molar mass | 86.090 g·mol−1 |
| Appearance | colorless oil |
| Density | 1.113 g/cm3 (18 °C)[1] |
| Melting point | 4 °C (39 °F; 277 K)[1] |
| Boiling point | 138 °C (280 °F; 411 K)[1] |
| Miscible[1] | |
| Vapor pressure | 0.52 kPa (at 20 °C)[2] |
| Hazards | |
| GHS labelling: | |
    | |
| Danger | |
| H226, H301, H310, H311, H314, H330, H340, H350 | |
| P201, P202, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501 | |
| Flash point | 46 °C (115 °F; 319 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Diepoxybutane describes organic compounds with the formula (CHOCH2)2. Three isomers are possible, a pair of enantiomers and a meso isomer. These compounds represent the simplest double epoxide. The isomers a colorless liquids.[3]
Diepoxybutane is used as a chemical intermediate, as a cross-linking agent for polymers and textiles, and as a preservative.[2]
t is prepared by ring closing reactions from an acetal derived from threitol.[3]
Reactions and uses
It reacts with Grignard reagents to undergo ring-opening reactions.[3]
Diepoxybutane is prone to polymerization.[4]
Diepoxybutane (DEB test) to screen for Fanconi anemia (FA) among patients with bone marrow failure syndromes.[5]
DEB effects DNA crosslinking.[6][7]
Toxicity and hazards
Diepoxybutane irritates the nose, throat and lungs, causing coughing and shortness of breath. Skin exposure can cause chemical burns. Longer exposure periods can cause pulmonary edema, and damage to the liver and kidneys.[8]
References
- 1 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- 1 2 Diepoxybutane Report on Carcinogens, Twelfth Edition (2011)
- 1 2 3 Robbins, Michael A.; Devine, Paul N.; Oh, Taeboem (1999). "Synthesis of Chiral Non-Racemic Diols from (S,S)-1,2,3,4-Diepoxybutane: (2S,3S)-Dihydroxy-1,4-Diphenylbutane". Organic Syntheses. 76: 101. doi:10.15227/orgsyn.076.0101.
- ↑ "Diepoxybutane". CAMEO Chemicals. NOAA. Retrieved 2023-03-19.
- ↑ "Diepoxybutane Test". www.datadictionary.nhs.uk. Retrieved 2023-03-19.
- ↑ Li, Yupeng (2024). "DNA Adducts in Cancer Chemotherapy". Journal of Medicinal Chemistry. 67 (7): 5113–5143. doi:10.1021/acs.jmedchem.3c02476. PMID 38552031.
- ↑ Auerbach, AD; Tserelov, AM (1 April 2015). "Diagnosis of Fanconi anemia by diepoxybutane analysis". Current Protocols in Human Genetics. 85: 8.7.1–8.7.17. doi:10.1002/0471142905.hg0807s85. PMC 4408609. PMID 25827349.
- ↑ New Jersey Department of Health and Senior Services (2000). Hazardous Substances Fact Sheet. 984-2202 (609). Retrieved 2023-03-20. https://nj.gov/health/eoh/rtkweb/documents/fs/0685.pdf.