| Revision as of 14:12, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 441605205 of page Trimethyl_phosphite for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 09:33, 23 October 2024 edit Citation bot (talk | contribs)Bots5,430,984 edits Removed parameters. | Use this bot. Report bugs. | Suggested by Dominic3203 | Category:Foul-smelling chemicals | #UCB_Category 53/128Tag: Manual revert |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 402697835 |
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| verifiedrevid = 470615330 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|ImageFile=P(OMe)3.png |
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| Name = |
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|ImageSize=200px |
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|IUPACName=Trimethyl phosphite |
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| ImageFile = Trimethyl phosphite structure.svg |
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| ImageSize = 165px |
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|OtherNames= Trimethoxyphosphine |
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| ImageFileL1 = Trimethyl phosphite Ball and Stick.png |
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|Section1= {{Chembox Identifiers |
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| ImageSizeL1 = 120px |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageFileR1 = Trimethyl phosphite Space Fill.png |
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| ImageSizeR1 = 120px |
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| PIN = Trimethyl phosphite<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page=931 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| SystematicName = |
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| OtherNames = Trimethoxyphosphine <br /> |
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Trimethoxyphosphane |
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| IUPACName = |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8159 |
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| ChemSpiderID = 8159 |
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| ChEBI = 183313 |
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| InChI = 1/C3H9O3P/c1-4-7(5-2)6-3/h1-3H3 |
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| InChI = 1/C3H9O3P/c1-4-7(5-2)6-3/h1-3H3 |
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| InChIKey = CYTQBVOFDCPGCX-UHFFFAOYAO |
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| InChIKey = CYTQBVOFDCPGCX-UHFFFAOYAO |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=121-45-9 |
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| CASNo=121-45-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 8472 |
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| SMILES = O(P(OC)OC)C |
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| UNII = 26Q0321ZDG |
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| PubChem = 8472 |
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| SMILES = COP(OC)OC |
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|Section2= {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula=C<sub>3</sub>H<sub>9</sub>O<sub>3</sub>P |
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| Formula=C<sub>3</sub>H<sub>9</sub>O<sub>3</sub>P |
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| MolarMass=124.08 |
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| MolarMass=124.08 |
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| Appearance=colorless liquid |
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| Appearance=colorless liquid |
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| Odor = distinctive, pungent<ref name=PGCH/> |
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| Density=1.052 |
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| Density=1.052 |
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| MeltingPtC=-78 |
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| MeltingPtC=-78 |
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| BoilingPtC=111 |
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| BoilingPtC=111 |
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| Solubility=organic solvents |
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| Solubility=reacts<ref name=PGCH/> |
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| VaporPressure = 24 mmHg (25°C)<ref name=PGCH/> |
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|Section3= {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| FlashPtF=82 |
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| FlashPt_ref = <ref name=PGCH/> |
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| IDLH = N.D.<ref name=PGCH>{{PGCH|0640}}</ref> |
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| REL = TWA 2 ppm (10 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| PEL = none<ref name=PGCH/> |
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| Section5 = {{Chembox Related |
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| OtherCompounds = ] |
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| Section6 = |
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}} |
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'''Trimethyl phosphite''' is an ] with the ] P(OCH<sub>3</sub>)<sub>3</sub>, often abbreviated P(OMe)<sub>3</sub>. It is a colorless liquid with a highly pungent odor. It is the simplest ] and finds used as a ] in ] and as a reagent in ]. The molecule features a pyramidal phosphorus(III) center bound to three ] groups. |
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==Synthesis== |
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Trimethyl phosphite is in principle obtainable by methanolysis of ], say in the presence of a proton accepting base. This method suffers from numerous side reactions however. The use of ] is superior:<ref>{{cite journal |doi=10.1021/ja01110a024|title=Preparation and Determination of Apparent Dissociation Constants of Some Alkylphosphonic and Dialkylphosphinic Acids1 |year=1953 |last1=Crofts |first1=Peter C. |last2=Kosolapoff |first2=Gennady M. |journal=Journal of the American Chemical Society |volume=75 |issue=14 |pages=3379–3383 }}</ref> |
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:{{chem2|PCl3 + 3 NaOCH3 → P(OCH3)3 + 3 NaCl}} |
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==Reactions== |
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Trimethyl phosphite is susceptible to oxidation to ]: |
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:{{chem2|P(OCH3)3 + 0.5 O2 → OP(OCH3)3 }} |
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It reacts with a catalytic amount of methyl iodide in the ] to give ]: |
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:P(OCH<sub>3</sub>)<sub>3</sub> → CH<sub>3</sub>P(O)(OCH<sub>3</sub>)<sub>2</sub> |
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As a ligand, trimethyl phosphite has a smaller ] and better acceptor properties relative to ]. A representative derivative is the colorless tetrahedral complex Ni(P(OMe)<sub>3</sub>)<sub>4</sub> (] 108 °C).<ref>{{cite book | author1 = Steven D. Ittel | author-link = Steven Ittel | last2 = Cushing | first2 = M. A. | chapter = Bis(1,5-Cyclooctadiene)Nickel(0) | title = Inorganic Syntheses | volume = 28 | pages = 98–104 | year = 1990 | doi = 10.1002/9780470132593.ch25 | isbn = 978-0-471-52619-3 }}</ref> The tridentate ligand called the ] is derived from trimethyl phosphite. The formation of this ligand illustrates the susceptibility of trimethyl phosphite (and metal complexes thereof) to the Arbuzov reaction. |
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Trimethyl phosphite is also used as a mild desulfurization reagent in organic synthesis, for example in the preparation of derivatives of ].<ref>{{cite journal|last1=Larsen|first1=Jan|last2=Lenoir|first2=Christine|date=1995|title=2,2'-Bi-5,6-Dihydro-1,3-Dithiolo<nowiki></nowiki>dithiinylidene (BEDT-TTF)|journal=]|volume=72|page=265|doi=10.15227/orgsyn.072.0265}}</ref> |
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==Toxicity== |
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The ] is 1600–2890 mg/kg (oral, rat).<ref name = Svara>{{ Ullmann | last1 = Svara| first1=J.| last2=Weferling| first2=N.| last3=Hofmann| first3=T. | title = Phosphorus Compounds, Organic | doi = 10.1002/14356007.a19_545.pub2}}</ref> |
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==References== |
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{{Reflist}} |
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==External links== |
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