5850-00-0

Usage

Uses

Used in Military Training and Chemical Detection:
(dimethylphosphinyl)methanol is used as a chemical warfare agent simulant for military training exercises, enabling the development and testing of protective gear and decontamination procedures. It is also utilized in the testing and calibration of chemical detection equipment, ensuring the accuracy and reliability of these systems in identifying potential chemical threats.
Used in Flame Retardant Production:
In the chemical industry, (dimethylphosphinyl)methanol is used as a component in the production of flame retardants, contributing to the development of materials that can resist ignition and slow the spread of fire, thereby enhancing safety in various applications.
Used in Synthesis of Nerve Agents:
Although its use is highly regulated due to ethical and safety concerns, (dimethylphosphinyl)methanol is recognized as a potential precursor in the synthesis of nerve agents, highlighting its dual-use nature in both beneficial and harmful applications.

InChI:InChI=1/C3H9O2P/c1-6(2,5)3-4/h4H,3H2,1-2H3

Synthetic route

(acetoxymethyl)dimethylphosphine oxide (50636-62-9) → (hydroxymethyl)-dimethylphosphine oxide (5850-00-0)

Conditions	Yield
With potassium hydroxide In methanol

Hydroxymethyl-dimethylphosphan (33796-25-7) → (hydroxymethyl)-dimethylphosphine oxide (5850-00-0)

Conditions	Yield
With dihydrogen peroxide

formaldehyd (50-00-0) + dimethyl phosphine oxide (7211-39-4) → (hydroxymethyl)-dimethylphosphine oxide (5850-00-0)

Conditions	Yield
In water

N,N-Dimethyltrimethylsilylamine (2083-91-2) + (hydroxymethyl)-dimethylphosphine oxide (5850-00-0) → (Trimethylsiloxymethyl)-dimethylphosphinoxid

Conditions	Yield
at 95℃; for 0.75h;	91%

formaldehyd (50-00-0) + (hydroxymethyl)-dimethylphosphine oxide (5850-00-0) → (Hydroxymethylmethoxy)-dimethylphosphinoxid

Conditions	Yield
With potassium methanolate In water at 100℃; for 3h;	80.8%

N-hydroxyphthalimide (524-38-9) + (hydroxymethyl)-dimethylphosphine oxide (5850-00-0) → 2-(Dimethyl-phosphinoylmethoxy)-isoindole-1,3-dione (145433-47-2)

Conditions	Yield
	68%

(hydroxymethyl)-dimethylphosphine oxide (5850-00-0) + diethylene glycol ditosylate (7460-82-4) → diethylene glycol bis<(dimethylphosphinyl)methyl> ether

Conditions	Yield
With sodium methylate In diethylene glycol dimethyl ether at 120 - 130℃; for 5h;	40%

(hydroxymethyl)-dimethylphosphine oxide (5850-00-0) → dimethyl(bromomethyl)phosphine oxide (37016-57-2)

Conditions	Yield
With Oxalyl bromide In dichloromethane

(hydroxymethyl)-dimethylphosphine oxide (5850-00-0) → dimethylchloromethylphosphine oxide (1638-75-1)

Conditions	Yield
With COCl2 In dichloromethane

flufenamic acid (530-78-9) + (hydroxymethyl)-dimethylphosphine oxide (5850-00-0) → dimethylphosphinyl-methyl N-(3-trifluoromethylphenyl)-anthranilate (61148-97-8)

Conditions	Yield
With hydrogenchloride In toluene at 110℃;

(hydroxymethyl)-dimethylphosphine oxide (5850-00-0) + p-toluenesulfonyl chloride (98-59-9) → (Tosylmethyl)dimethylphosphinoxid

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃; Tosylation;	23.42 g

Upstream product

• 50636-62-9 dimethyl(acetoxymethyl)phosphine oxide 
• 50-00-0 formaldehyd 
• 7211-39-4 dimethyl phosphine oxide 
• 33796-25-7 Hydroxymethyl-dimethylphosphan 

Downstream Products

• 61148-97-8 dimethylphosphinyl-methyl N-(3-trifluoromethylphenyl)-anthranilate 
• 1638-75-1 dimethylchloromethylphosphine oxide 

Relevant academic research and scientific papers

The effect of the phosphoryl group on the rate and mechanism of SN-substitution at the saturated carbon atoms

The reactivity of diarylphosphine oxides RR'P(O)CH2X with p-O2NC6H4ONa in DMF have been studied.The reaction rate increases with the electrodrawing properties of the substituents on R and R' in the following way: p-Me2NC6H4 2 reaction rate of diphenylphosphine oxides has been investigated.The reactivity increases as follows Cl I Br OTs.A reaction mechanism is suggested.

Production of tertiary (hydroxymethyl)-methylphosphine oxides

Production of tertiary (hydroxymethyl)-methylphosphine oxides of the general formula: STR1 in which R stands for a branched or unbranched, substituted or unsubstituted alkyl, cycloalkyl, aralkyl or aryl group having from 1 to 18 carbon atoms. To this end tertiary bis-(hydroxymethyl)-phosphines of the general formula STR2 in which R has the meaning given above, are subjected to a thermal rearrangement reaction at temperatures higher than about 90° C or at temperatures within the range -10° and +250° C, in the presence of a catalyst.

Production of methylphosphine oxides

Methylphosphine oxides of the general formula (I) EQU1 are produced from hydroxymethylphosphines of the general formula (II) EQU2 in which formulae R and R' each stand for identical or different alkyl-, cycloalkyl-, aralkyl- or aryl groups having from 1 to 18 carbon atoms, or carrying substituents being inert under the reaction conditions. The methylphosphine oxides are more particularly produced by subjecting the hydroxymethylphosphines to a rearrangement reaction with the aid of radical-yielding compounds.