TBPO
 | |
| Names | |
|---|---|
| Preferred IUPAC name 4-tert-Butyl-2,6,7-trioxa-1λ5-phosphabicyclo[2.2.2]octan-1-one | |
| Other names t-Butyl-bicyclophosphate | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| |
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| Properties | |
| C8H15O4P | |
| Molar mass | 206.178 g·mol−1 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Extremely toxic |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
36 μg/kg (mice) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
TBPO is an extremely toxic bicyclic phosphate convulsant and GABA receptor antagonist. It is the most toxic bicyclic phosphate known, with an LD50 of 36 μg/kg in mice.[2]
Some sources claim that TBPO is as toxic as VX.[3]
Synthesis
The synthesis is equivalent to the synthesis of IPTBO while the triol is produced by the condensation between 3,3-dimethylbutyraldehyde and formaldehyde analogous to the synthesis of trimethylolpropane.
See also
References
- ^ Zhao, C.; Hwang, S. H.; Buchholz, B. A.; Carpenter, T. S.; Lightstone, F. C.; Yang, J.; Hammock, B. D.; Casida, J. E. (27 May 2014). "GABAA receptor target of tetramethylenedisulfotetramine". Proceedings of the National Academy of Sciences. 111 (23): 8607–8612. Bibcode:2014PNAS..111.8607Z. doi:10.1073/pnas.1407379111. PMC 4060666. PMID 24912155.
- ^ Milbrath, Dean S.; Engel, Judith L.; Verkade, John G.; Casida, John E. (February 1979). "Structure-toxicity relationships of 1-substituted-4-alkyl-2,6,7-trioxabicyclo[2.2.2.]octanes". Toxicology and Applied Pharmacology. 47 (2): 287–293. Bibcode:1979ToxAP..47..287M. doi:10.1016/0041-008x(79)90323-5. PMID 452023.
- ^ Gupta RC (2015). Handbook of toxicology of chemical warfare agents (2nd ed.). Amsterdam: Elsevier/Academic Press. pp. 228–229. ISBN 9780128004944. OCLC 433545336.
