Trimethyl phosphite

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Trimethyl phosphite
Trimethyl phosphite structure.svg
Trimethyl phosphite Ball and Stick.png
Trimethyl phosphite Space Fill.png
Names
Preferred IUPAC name
Trimethyl phosphite [1]
Other names
Trimethoxyphosphine
Trimethoxyphosphane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.065 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C3H9O3P/c1-4-7(5-2)6-3/h1-3H3 Yes check.svgY
    Key: CYTQBVOFDCPGCX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H9O3P/c1-4-7(5-2)6-3/h1-3H3
    Key: CYTQBVOFDCPGCX-UHFFFAOYAO
  • COP(OC)OC
Properties
C3H9O3P
Molar mass 124.08
Appearancecolorless liquid
Odor distinctive, pungent [2]
Density 1.052
Melting point −78 °C (−108 °F; 195 K)
Boiling point 111 °C (232 °F; 384 K)
reacts [2]
Vapor pressure 24 mmHg (25°C) [2]
Hazards
Flash point 28 °C; 82 °F; 301 K [2]
NIOSH (US health exposure limits):
PEL (Permissible)
none [2]
REL (Recommended)
TWA 2 ppm (10 mg/m3) [2]
IDLH (Immediate danger)
N.D. [2]
Related compounds
Related compounds
 Dimethyl methylphosphonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trimethyl phosphite is an organophosphorus compound with the formula P(OCH3)3, often abbreviated P(OMe)3. It is a colorless liquid with a highly pungent odor. It is the simplest phosphite ester and finds used as a ligand in organometallic chemistry and as a reagent in organic synthesis. The molecule features a pyramidal phosphorus(III) center bound to three methoxy groups.

Contents

Synthesis

Trimethyl phosphite is in principle obtainable by methanolysis of phosphorus trichloride, say in the presence of a proton accepting base. This method suffers from numerous side reactions however. The use of sodium methoxide is superior: [3]

PCl3 + 3 NaOCH3 → P(OCH3)3 + 3 NaCl

Reactions

Trimethyl phosphite is susceptible to oxidation to trimethyl phosphate:

P(OCH3)3 + 0.5 O2 → OP(OCH3)3

It reacts with a catalytic amount of methyl iodide in the Arbuzov reaction to give dimethyl methylphosphonate:

P(OCH3)3 → CH3P(O)(OCH3)2

As a ligand, trimethyl phosphite has a smaller cone angle and better acceptor properties relative to trimethylphosphine. A representative derivative is the colorless tetrahedral complex Ni(P(OMe)3)4 (m.p. 108 °C). [4] The tridentate ligand called the Kläui ligand is derived from trimethyl phosphite. The formation of this ligand illustrates the susceptibility of trimethyl phosphite (and metal complexes thereof) to the Arbuzov reaction.

Trimethyl phosphite is also used as a mild desulfurization reagent in organic synthesis, for example in the preparation of derivatives of tetrathiafulvalene. [5]

Toxicity

The LD50 is 1600–2890 mg/kg (oral, rat). [6]

Related Research Articles

Dimethylformamide is an organic compound with the chemical formula HCON(CH3)2. Its structure is HC(=O)−N(−CH3)2. Commonly abbreviated as DMF, this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

<span class="mw-page-title-main">Phosphonium</span> Family of polyatomic cations containing phosphorus

In chemistry, the term phosphonium describes polyatomic cations with the chemical formula PR+
4. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.

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

Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides/oxychlorides, others being PCl3 and POCl3. PCl5 finds use as a chlorinating reagent. It is a colourless, water-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride.

<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">Michaelis–Arbuzov reaction</span>

The Michaelis–Arbuzov reaction is the chemical reaction of a trivalent phosphorus ester with an alkyl halide to form a pentavalent phosphorus species and another alkyl halide. The picture below shows the most common types of substrates undergoing the Arbuzov reaction; phosphite esters (1) react to form phosphonates (2), phosphonites (3) react to form phosphinates (4) and phosphinites (5) react to form phosphine oxides (6).

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

Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula [(CH3)2N]3PO. This colorless liquid is a useful reagent in organic synthesis.

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

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

<span class="mw-page-title-main">Malononitrile</span> Organic compound with formula CH2(CN)2

Malononitrile is an organic compound nitrile with the formula CH2(CN)2. It is a colorless or white solid, although aged samples appear yellow or even brown. It is a widely used building block in organic synthesis.

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

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colorless liquid is the simplest aromatic thiol. The chemical structures of thiophenol and its derivatives are analogous to phenols. An exception is the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, in the case of 'thiol' that the alcohol oxygen atom is replaced by a sulfur atom.

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

Phosphorus pentasulfide is the inorganic compound with the formula P2S5 (empirical) or P4S10 (molecular). This yellow solid is the one of two phosphorus sulfides of commercial value. Samples often appear greenish-gray due to impurities. It is soluble in carbon disulfide but reacts with many other solvents such as alcohols, DMSO, and DMF.

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

Dimethyl methylphosphonate is an organophosphorus compound with the chemical formula CH3PO(OCH3)2. It is a colourless liquid, which is primarily used as a flame retardant.

<span class="mw-page-title-main">Phosphite ester</span> Organic compound with the formula P(OR)3

In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3. They can be considered as esters of an unobserved tautomer phosphorous acid, H3PO3, with the simplest example being trimethylphosphite, P(OCH3)3. Some phosphites can be considered esters of the dominant tautomer of phosphorous acid (HP(O)(OH)2). The simplest representative is dimethylphosphite with the formula HP(O)(OCH3)2. Both classes of phosphites are usually colorless liquids.

Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which 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 insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.

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

Sulfur tetrafluoride is a chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous hydrogen fluoride gas upon exposure to water or moisture. Sulfur tetrafluride is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

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

Antimony trifluoride is the inorganic compound with the formula SbF3. Sometimes called Swarts' reagent, it is one of two principal fluorides of antimony, the other being SbF5. It appears as a white solid. As well as some industrial applications, it is used as a reagent in inorganic and organofluorine chemistry.

Organophosphines are organophosphorus compounds with the formula PRnH3−n, where R is an organic substituent. These compounds can be classified according to the value of n: primary phosphines (n = 1), secondary phosphines (n = 2), tertiary phosphines (n = 3). All adopt pyramidal structures. Organophosphines are generally colorless, lipophilic liquids or solids. The parent of the organophosphines is phosphine (PH3).

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

Trimethylolpropane phosphite, C2H5C(CH2O)3P, is a phosphite ester used as a ligand in organometallic chemistry. Trimethylolpropane phosphite is sometimes abbreviated to EtCage. It is a white solid that is soluble in organic solvents. It is also highly toxic.

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

Triethyl phosphite is an organophosphorus compound, specifically a phosphite ester, with the formula P(OCH2CH3)3, often abbreviated P(OEt)3. It is a colorless, malodorous liquid. It is used as a ligand in organometallic chemistry and as a reagent in organic synthesis.

Phenylphosphine is an organophosphorus compound with the chemical formula C6H5PH2. It is the phosphorus analog of aniline. Like other primary phosphines, phenylphosphine has an intense penetrating odor and is highly oxidizable. It is mainly used as a precursor to other organophosphorus compounds. It can function as a ligand in coordination chemistry.

<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 931. doi:10.1039/9781849733069-FP001 (inactive 2024-06-30). ISBN   978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of June 2024 (link)
  2. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0640". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ Crofts, Peter C.; Kosolapoff, Gennady M. (1953). "Preparation and Determination of Apparent Dissociation Constants of Some Alkylphosphonic and Dialkylphosphinic Acids1". Journal of the American Chemical Society. 75 (14): 3379–3383. doi:10.1021/ja01110a024.
  4. ↑ Steven D. Ittel; Cushing, M. A. (1990). "Bis(1,5-Cyclooctadiene)Nickel(0)". Inorganic Syntheses. Vol. 28. pp. 98–104. doi:10.1002/9780470132593.ch25. ISBN   978-0-471-52619-3.
  5. ↑ Larsen, Jan; Lenoir, Christine (1995). "2,2'-Bi-5,6-Dihydro-1,3-Dithiolo[4,5-b][1,4]dithiinylidene (BEDT-TTF)". Org. Synth. 72: 265. doi:10.15227/orgsyn.072.0265.
  6. ↑ Svara, J.; Weferling, N.; Hofmann, T. "Phosphorus Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_545.pub2. ISBN   978-3527306732.
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