TBPO

TBPO^[1]
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
CAS Number	61481-19-4;
3D model (JSmol)	Interactive image;
ChemSpider	39799;
PubChem CID	43673;
CompTox Dashboard (EPA)	DTXSID80977049 ;
	InChI 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;
	SMILES CC(C)(C)C12COP(=O)(OC1)OC2;
Properties
Chemical formula	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). Infobox references

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]

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Some sources claim that TBPO is as toxic as VX.^[3]

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.

[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.

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Synthesis

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
CAS Number	61481-19-4
3D model (JSmol)	Interactive image
ChemSpider	39799
PubChem CID	43673
CompTox Dashboard (EPA)	DTXSID80977049
InChI 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
SMILES CC(C)(C)C12COP(=O)(OC1)OC2
Properties
Chemical formula	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). Infobox references