5850-00-0

Basic information

• Product Name: (dimethylphosphinyl)methanol
• Synonyms: (dimethylphosphinyl)methanol;Einecs 227-442-9;HYDROXYMETHYL -DIMETHYLPHOSPHINOXIDE
• CAS NO: 5850-00-0
• Molecular Formula: C3H9O2P
• Molecular Weight: 108.076121
• EINECS: 227-442-9
• Mol File: 5850-00-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 81.5-82.5 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 298.4°Cat760mmHg
• Flash Point: 134.2°C
• Appearance: /
• Density: 1.083g/cm³
• Vapor Pressure: 0.000129mmHg at 25°C
• Refractive Index: 1.403
• PKA: 13.14±0.10(Predicted)
• CAS DataBase Reference: (dimethylphosphinyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (dimethylphosphinyl)methanol(5850-00-0)
• EPA Substance Registry System: (dimethylphosphinyl)methanol(5850-00-0)

Safety Data

• Hazardous Substances Data: 5850-00-0(Hazardous Substances Data)

Usage

General Description

(Dimethylphosphinyl)methanol, also known as DMMP, is a colorless liquid chemical compound that is primarily used as a chemical warfare agent simulant and in the production of flame retardants. It is highly soluble in water and has a pungent odor. DMMP is also used in military training exercises and in the testing and calibration of chemical detection equipment. It is a phosphonic acid derivative and has been identified as a potential precursor for the synthesis of nerve agents. Due to its potential use in chemical warfare, there are strict regulations on its production, handling, and transportation.

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

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

Downstream Products

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

Relevant articles and documents

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 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.