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.[1]
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Names | |||
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Preferred IUPAC name
4-Ethyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane | |||
Other names
EtCage; Ethyl bicyclic phosphite; Trishydroxymethylpropane bicyclic phosphite
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Identifiers | |||
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ECHA InfoCard | 100.011.385 | ||
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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 [77 °F], 100 kPa).
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Infobox references
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It is prepared by reaction of trimethylolpropane with phosphorus trichloride or by transesterification with trimethylphosphite:[2]
The first member of this series was derived from trimethylolethane,[3] but these derivatives are often poorly soluble. For this reason, the ethyl derivative has received more attention.[4]
The compound forms an isolable ozonide, which degrades above 0 °C to release singlet O2.[1]
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 [(EtCage)2Mo(CO)4], [Ir4(CO)11(EtCage)] and (CpMe5)RuCl(EtCage)2, shown below.
Trimethylolpropane phosphite is very toxic and is a convulsant. LD50 is 1.1 mg per kg bodyweight (mice, i.p.).[5][6]