Dimethylphosphine oxide

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Dimethylphosphine oxide
Me2P(O)H.png
Names
Preferred IUPAC name
Dimethyl-λ5-phosphanone
Other names
dimethylphosphinous acid tautomer
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 230-591-2
PubChem CID
  • InChI=1S/C2H7OP/c1-4(2)3/h4H,1-2H3
    Key: HGDIHUZVQPKSMO-UHFFFAOYSA-N
  • CP(=O)C
Properties
C2H7OP
Molar mass 78.051 g·mol−1
Appearancecolorless liquid
Boiling point 65–67 ºC
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dimethylphosphine oxide is an organophosphorus compound with the formula (CH3)2P(O)H. It is a colorless liquid that soluble in polar organic solvents. It exists as the phosphine oxide, not the hydroxy tautomer. A related compound is diphenylphosphine oxide. Both are sometimes called secondary phosphine oxides.

Contents

Preparation

The compound arises by the hydrolysis of chlorodimethylphosphine: [1]

Me2PCl + H2O → Me2P(O)H + HCl

Methanol, but not ethanol, can also be used in place of water, the co-product being methyl chloride.

Since chlorodimethylphosphine is dangerous to handle, alternative routes to dimethylphosphine oxide have been developed. A popular method starts with diethylphosphite, according to the following idealized equations: [2]

(C2H5O)2P(O)H + 3 CH3MgBr → (CH3)2P(O)MgBr + 2 MgBr(OC2H5) + CH4
(CH3)2P(O)MgBr + H2O → (CH3)2P(O)H + 2 MgBr(OH)

Reactions

Chlorination gives dimethylphosphoryl chloride. It undergoes hydroxymethylation with formaldehyde.

Me2P(O)H + CH2O → Me2P(O)CH2OH

Many aldehydes effect a similar reaction.

Related Research Articles

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4
. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.

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<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

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<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

A Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

<span class="mw-page-title-main">Phosphine oxide</span> Class of chemical compounds

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<span class="mw-page-title-main">Tetrakis(hydroxymethyl)phosphonium chloride</span> Chemical compound

Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. The cation P(CH2OH)4+ is four-coordinate, as is typical for phosphonium salts. THPC has applications as a precursor to fire-retardant materials, as well as a microbiocide in commercial and industrial water systems.

<span class="mw-page-title-main">Dimethylphenylphosphine</span> Chemical compound

Dimethylphenylphosphine is an organophosphorus compound with a formula P(C6H5)(CH3)2. The phosphorus is connected to a phenyl group and two methyl groups, making it the simplest aromatic alkylphosphine. It is colorless air sensitive liquid. It is a member of series (CH3)3-n(C6H5)2P that also includes n = 0, n = 2, and n = 3 that are often employed as ligands in metal phosphine complexes.

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<span class="mw-page-title-main">Diphenylphosphine oxide</span> Chemical compound

Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents.

<span class="mw-page-title-main">Diethylphosphite</span> Chemical compound

Diethylphosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethylphosphite is a colorless liquid. The molecule is tetrahedral.

In organophosphorus chemistry, an aminophosphine is a compound with the formula R3−nP(NR2)n where R = H or an organic substituent, and n = 0, 1, 2. At one extreme, the parent H2PNH2 is lightly studied and fragile, but at the other extreme tris(dimethylamino)phosphine (P(NMe2)3) is commonly available. Intermediate members are known, such as Ph2PN(H)Ph. These compounds are typically colorless and reactive toward oxygen. They have pyramidal geometry at phosphorus.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

References

  1. Kleiner, H. J. (1974). "Herstellung und Umsetzungen von Dimethylphosphinoxid (Preparation and Reactions of Dimethylphosphine Oxide)". Justus Liebigs Ann. Chem.: 751–764. doi:10.1002/jlac.197419740507.
  2. Hays, H. R. (1968). "Reaction of diethyl phosphonate with methyl and ethyl Grignard reagents". J. Org. Chem. 33: 3690–3694. doi:10.1021/jo01274a003.