Trimethylphosphine

Structural formula
General
Surname	Trimethylphosphine
other names	PMe 3 Trimethylphosphine
Molecular formula	C 3 H 9 P
Brief description	colorless liquid with a pungent odor
External identifiers / databases
CAS number 594-09-2 EC number 209-823-1 ECHA InfoCard 100.008.932 PubChem 68983 Wikidata Q3268860
properties
Molar mass	76.08 g mol −1
Physical state	liquid
density	0.738 g cm −3 (20 ° C)
Melting point	−86 ° C
boiling point	38-40 ° C
Vapor pressure	499 hPa (20 ° C)
solubility	almost insoluble in water soluble in aliphatic, aromatic and ethereal solvents
Refractive index	1.428 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225-315-319-335 P: 210-261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Trimethylphosphine with the constitutional formula P (CH ₃ ) ₃ is an inorganic chemical compound from the group of phosphines .

Extraction and presentation

Trimethylphosphine can be obtained by reacting triphenylphosphite with methylmagnesium chloride.

${\displaystyle \mathrm {3\ CH_{3}MgCl+P(OC_{6}H_{5})_{3}\longrightarrow P(CH_{3})_{3}+3\ C_{6}H_{5}OMgCl} }$

properties

Trimethylphosphine is a clear, colorless liquid with a pungent odor that is insoluble in water.

use

Electron-rich phosphine ligands such as trimethylphosphine are used in numerous applications such as cross-coupling reactions. It is used as a reagent in the Mitsunobu reaction , the conversion of azides into carbamates , aziridines from azido alcohols, the production of iminophosphoranes and in the aza-Wittig reaction .

Individual evidence

1. ↑ ^{a b c d e f g h i j k} data sheet Trimethylphosphine, 97% from Sigma-Aldrich , accessed on July 28, 2014 ( PDF ).
2. ↑ ^{a b} Data sheet Trimethylphosphine, 99% from AlfaAesar, accessed on July 28, 2014 ( PDF )(JavaScript required) .
3. ^ ^{A b} William M. Haynes: CRC Handbook of Chemistry and Physics, 93rd Edition . CRC Press, 2012, p. 538 ( limited preview in Google Book search).
4. ↑ Optimachem: Trimethylphosphine 30% in THF
5. ↑ Leutkens, Jr., ML; Sattelberger, AP; Murray, HH; Basil, JD; Fackler, Jr. JP (1990). "Trimethylphosphine". In Robert J. Angelici. Inorganic Syntheses. Inorganic Syntheses (New York: J. Wiley & Sons) 28 : 305-310. doi : 10.1002 / 9780470132593.ch76 . ISBN 0-471-52619-3 .