TBPO

{{Chembox

| ImageFile = TBPO.svg

| ImageSize = 120px

| PIN=4-tert-Butyl-2,6,7-trioxa-1λ5-phosphabicyclo[2.2.2]octan-1-one

| OtherNames= t-Butyl-bicyclophosphate

| Name = TBPO{{cite journal |last1=Zhao |first1=C. |last2=Hwang |first2=S. H. |last3=Buchholz |first3=B. A. |last4=Carpenter |first4=T. S. |last5=Lightstone |first5=F. C. |last6=Yang |first6=J. |last7=Hammock |first7=B. D. |last8=Casida |first8=J. E. |title=GABAA receptor target of tetramethylenedisulfotetramine |journal=Proceedings of the National Academy of Sciences |date=27 May 2014 |volume=111 |issue=23 |pages=8607–8612 |doi=10.1073/pnas.1407379111 |pmid=24912155 |pmc=4060666|bibcode=2014PNAS..111.8607Z |doi-access=free }}

| Section1 = {{Chembox Identifiers

| CASNo = 61481-19-4

| ChemSpiderID = 39799

| PubChem = 43673

| StdInChI=1S/C8H15O4P/c1-7(2,3)8-4-10-13(9,11-5-8)12-6-8/h4-6H2,1-3H3

| StdInChIKey = CNBZOKKOTFTYLW-UHFFFAOYSA-N

| SMILES = CC(C)(C)C12COP(=O)(OC1)OC2

}}

| Section2 = {{Chembox Properties

| C=8|H=15|O=4|P=1

}}

| Section3 = {{Chembox Hazards

| MainHazards = Extremely toxic

| LD50 = 36 μg/kg (mice)

}}

}}

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.{{cite journal |last1=Milbrath |first1=Dean S. |last2=Engel |first2=Judith L. |last3=Verkade |first3=John G. |last4=Casida |first4=John E. |title=Structure-toxicity relationships of 1-substituted-4-alkyl-2,6,7-trioxabicyclo[2.2.2.]octanes |journal=Toxicology and Applied Pharmacology |date=February 1979 |volume=47 |issue=2 |pages=287–293 |doi=10.1016/0041-008x(79)90323-5 |pmid=452023|bibcode=1979ToxAP..47..287M }}

Some sources claim that TBPO is as toxic as VX.{{Cite book|title=Handbook of toxicology of chemical warfare agents|last=Gupta|first=Ramesh Chandra | name-list-style = vanc |publisher=Elsevier/Academic Press|year=2015|isbn=9780128004944|edition= 2nd|location=Amsterdam|pages=228–229|oclc=433545336}}

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