Tris(hydroxymethyl)phosphine is the
organophosphorus compound
Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...
with the formula P(CH
2OH)
3. It is a white solid. The compound is multifunctional, consisting of three
alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
functional groups and a
tertiary phosphine. It is prepared by treating
tetrakis(hydroxymethyl)phosphonium chloride with strong base:
:
(CH2OH)4l + NaOH → P(CH
2OH)
3 + H
2O + H
2C=O + NaCl
The compound can be prepared on a large scale using
triethylamine as base and as solvent.
Reactions
The compound forms complexes with a variety of metals. These complexes display some solubility in water but more so in methanol.
[
The compound decomposes violently to phosphine and formaldehyde upon attempted distillation. In air, it oxidizes to the oxide.
Upon heating with hexamethylenetetramine, it converts to triazaphosphaadamantane.][{{cite journal , doi=10.1002/jhet.5570110326, title=Synthesis of a Monophosphorus Analog of Hexamethylenetetramine, year=1974, last1=Daigle, first1=D. J., last2=Pepperman, first2=A. B., last3=Vail, first3=Sidney L., journal=Journal of Heterocyclic Chemistry, volume=11, issue=3, pages=407–408]
References
Tertiary phosphines