3-IODO-2-TRIMETHYLSILYLMETHYL-1-PROPENE Property

Boiling point:

185.6±28.0 °C(Predicted)

Density 

1.313±0.06 g/cm3(Predicted)

solubility 

wide range of organic solvents.

Hazard and Precautionary Statements (GHS)

3-IODO-2-TRIMETHYLSILYLMETHYL-1-PROPENE Chemical Properties,Usage,Production

Physical properties

bp 25 °C/0.5 mmHg.

Uses

3-Iodo-2-trimethylsilylmethyl-1-propene is widely used as a bifunctional conjunctive reagent that serves as a dipolar trimethylenemethane synthon; treatment with SnF2 affords a dianionic trimethylenemethane synthon.The most common use of this reagent is as a 1,3-dipolar synthon for trimethylenemethane (TMM).

Preparation

From the corresponding mesylate upon treatment with sodium iodide in acetone. The mesylate can be prepared from the commercially available alcohol.

storage

3-Iodo-2-trimethylsilylmethyl-1-propene can be stored in the dark at -20 °C for up to 3 months without significant deterioration.

References

1. Review of TMM and equivalents: Trost, B. M. AG(E) 1986, 25, 1.
2. Trost, B. M.; Curran, D. P. TL 1981, 22, 5023.
3. The alcohol can be prepared in two steps from 2-methyl-2-propen-1-ol: Trost, B. M.; Chan, D. M. T.; Nanninga, T. OS 1984, 62, 58.
4. Trost, B. M.; Curran, D. P. JACS 1981, 103, 7380.
5. Posner, G. H.; Asirvatham, E.; Hamill, T. G. JOC 1990, 55, 2132.