Trimethylolpropane phosphite

In today's article we are going to delve into the fascinating world of Trimethylolpropane phosphite. From its origins to its impact on modern society, Trimethylolpropane phosphite has been a topic of constant interest and debate. Over the years, Trimethylolpropane phosphite has evolved and adapted to social, technological and cultural changes. In this article, we will explore the different facets of Trimethylolpropane phosphite and analyze its influence on various aspects of daily life. Whether on a personal, professional or global level, Trimethylolpropane phosphite has left his mark on our world in multiple ways, and it is essential to understand his importance and reach. Join us on this journey of discovery and reflection about Trimethylolpropane phosphite.

Trimethylolpropane phosphite
Names
Preferred IUPAC name
4-Ethyl-2,6,7-trioxa-1-phosphabicyclooctane
Other names
EtCage; Ethyl bicyclic phosphite; Trishydroxymethylpropane bicyclic phosphite
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.385 Edit this at Wikidata
EC Number
  • 212-523-3
UNII
  • InChI=1S/C6H11O3P/c1-2-6-3-7-10(8-4-6)9-5-6/h2-5H2,1H3 ☒N
    Key: QRUSNTDXJQBKBI-UHFFFAOYSA-N ☒N
  • InChI=1/C6H11O3P/c1-2-6-3-7-10(8-4-6)9-5-6/h2-5H2,1H3
    Key: QRUSNTDXJQBKBI-UHFFFAOYAD
  • O1P2OCC(CC)(C1)CO2
Properties
C6H11O3P
Molar mass 162.125 g·mol−1
Appearance white waxy solid
Melting point 56 °C (133 °F; 329 K)
organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
☒N verify (what is checkY☒N ?)

Trimethylolpropane phosphite, C2H5C(CH2O)3P, is a phosphite ester used as a ligand in organometallic chemistry. Trimethylolpropane phosphite is sometimes abbreviated to EtCage. It is a white solid that is soluble in organic solvents. It is also highly toxic.

Preparation and reactions

It is prepared by reaction of trimethylolpropane with phosphorus trichloride or by transesterification with trimethylphosphite:

P(OMe)3 + EtC(CH2OH)3 → 3 MeOH + EtC(CH2O)3P

The first member of this series was derived from trimethylolethane, but these derivatives are often poorly soluble. For this reason, the ethyl derivative has received more attention.

Reactions

The compound forms an isolable ozonide, which degrades above 0 °C to release singlet O2.

Coordination chemistry

Several EtCage complexes are known, since the ligand is highly basic (for a phosphite) and has a small ligand cone angle (101°). Illustrative complexes include , and (CpMe5)RuCl(EtCage)2, shown below.

Ball-and-stick model of the bis(trimethylolpropane phosphite)molybdenum tetracarbonyl complex Ball-and-stick model of the (trimethylolpropane phosphite)tetrairidium undecacarbonyl cluster

Safety

Trimethylolpropane phosphite is very toxic and is a convulsant. LD50 is 1.1 mg per kg bodyweight (mice, i.p.).

References

  1. ^ a b Ende, Christopher; Parker, Kathlyn (2014). "4-Ethyl-2,6,7-trioxa-1-phosphabicyclooctane". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–3. doi:10.1002/047084289X.rn01781. ISBN 9780470842898.
  2. ^ Verkade, J. G. "Spectroscopic studies of metal-phosphorus bonding in coordination complexes" Coordination Chemistry Reviews 1972, vol. 9, 1-106. doi:10.1016/S0010-8545(00)80224-6
  3. ^ Verkade, J. G.; Reynolds, L. T. "The synthesis of a novel ester of phosphorus and of arsenic" Journal of Organic Chemistry (1960), 25, 663-5. doi:10.1021/jo01074a622
  4. ^ Huttemann, T. J., Jr.; Foxman, B. M.; Sperati, C. R.; Verkade, J. G. "Transition metal complexes of a constrained phosphite ester. IV. Compounds of cobalt(I), cobalt(III), nickel(II), and nickel(0)" Inorganic Chemistry (1965), 4(7), 950-3. doi:10.1021/ic50029a005
  5. ^ Ralf Stöhr et al. Chemische Kampfstoffe und Schutz vor chemischen Kampfstoffen 2. Aufl. Militärverlag der DDR, 1985 (german)
  6. ^ Milbrath, Dean S.; Engel, Judith L.; Verkade, John G.; Casida, John E. (1979). "Structure-toxicity relationships of 1-substituted-4-alkyl-2,6,7-trioxabicyclooctanes". Toxicology and Applied Pharmacology. 47 (2): 287–93. doi:10.1016/0041-008X(79)90323-5. PMID 452023.
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