TBPO

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)
ChemSpider
  • InChI=1S/C8H15O4P/c1-7(2,3)8-4-10-13(9,11-5-8)12-6-8/h4-6H2,1-3H3
    Key: CNBZOKKOTFTYLW-UHFFFAOYSA-N
  • CC(C)(C)C12COP(=O)(OC1)OC2
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):
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.

Some sources claim that TBPO is as toxic as VX.

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

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ Gupta RC (2015). Handbook of toxicology of chemical warfare agents (2nd ed.). Amsterdam: Elsevier/Academic Press. pp. 228–229. ISBN 9780128004944. OCLC 433545336.