(Difference between pages)

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

Content deleted Content addedVisualWikitext

Revision as of 14:03, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 465046984 of page Triethyl_phosphite for the Chem/Drugbox validation project (updated: '').		Latest revision as of 17:30, 17 December 2024 edit Comfr (talk | contribs)Extended confirmed users10,606 edits +acronym
Line 1:		Line 1:
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 402695657		| verifiedrevid = 470614115
	|ImageFile=P(OEt)3.png		| ImageFile =Triethyl phosphite-3D-balls-by-AHRLS-2011.png
			| ImageFile1 =P(OEt)3.png
	|ImageSize=200px
	|IUPACName=Triethyl phosphite		| PIN =Triethyl phosphite
	|OtherNames= Triethoxyphosphine		| OtherNames = Triethoxyphosphine
	|Section1= {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 28956		| ChemSpiderID = 28956
	| InChI = 1/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3		| InChI = 1/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3
Line 17:		Line 16:
	| StdInChIKey = BDZBKCUKTQZUTL-UHFFFAOYSA-N		| StdInChIKey = BDZBKCUKTQZUTL-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=122-52-1		| CASNo =122-52-1
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem = 31215
			| UNII = 6B2R04S55G
⚫	| SMILES = O(P(OCC)OCC)CC
		⚫	| PubChem = 31215
		⚫	| SMILES = O(P(OCC)OCC)CC
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
			| C=6|H=15|O=3|P=1
	| Formula=C<sub>6</sub>H<sub>15</sub>O<sub>3</sub>P
		⚫	| Appearance =colorless liquid
	| MolarMass=166.16 g/mol
		⚫	| Density =0.969 g/mL
⚫	| Appearance=colorless liquid
			| MeltingPtC =-70
⚫	| Density=0.969 g/mL
			| BoilingPtC = 156
	| MeltingPtC=-70
	| BoilingPt=156&nbsp;°C (57–58&nbsp;°C/16 mm)		| BoilingPt_notes = (57 to 58&nbsp;°C at 16 mm)<!-- 16 mmHg ? -->
	| Solubility=organic solvents		| SolubleOther = soluble in most organic solvents
			| MagSus = -104.8·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	|Section3= {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=toxic
			| MainHazards =toxic
	| FlashPt=
		⚫	}}
	| Autoignition=
⚫	}}
	}}		}}
			'''Triethyl phosphite (TEP)''' is an ], specifically a ], with the ] P(OCH<sub>2</sub>CH<sub>3</sub>)<sub>3</sub>, often abbreviated P(OEt)<sub>3</sub>. It is a colorless, malodorous liquid. It is used as a ] in ] and as a reagent in ].
			The molecule features a pyramidal phosphorus(III) center bound to three ethoxide groups. Its <sup>31</sup>P ] spectrum features a signal at around +139 ppm vs phosphoric acid standard.
			Triethylphosphite is prepared by treating ] with ] in the presence of a base, typically a tertiary amine:<ref>{{cite journal|first1=A. H.|last1=Ford-Moore|first2=B. J.|last2=Perry |journal=Org. Synth.| title = Triethyl Phosphite | volume=31 | pages = 111| year = 1951 | doi=10.15227/orgsyn.031.0111}}</ref>
			:PCl<sub>3</sub> + 3 EtOH + 3 R<sub>3</sub>N → P(OEt)<sub>3</sub> + 3 R<sub>3</sub>NH + 3 Cl<sup>−</sup>
			In the absence of the base, the reaction of ethanol and phosphorus trichloride affords ] ((EtO)<sub>2</sub>P(O)H). Of the many related compounds can be prepared similarly, triisopropyl phosphite is an example (b.p.&nbsp;43.5&nbsp;°C/1.0&nbsp;mm; CAS# 116-17-6).
			==Reactions==
			Triethyl phosphite can react with electrophiles in a ] to produce organophosphonates. For example, the reaction between triethyl phosphite and ] produces a phosphonate suitable for use in the ].<ref name="eEROS">{{cite journal |last1=Piscopio |first1=Anthony D. |last2=Shakya |first2=Sagar |title=Triethyl Phosphite |journal=Encyclopedia of Reagents for Organic Synthesis |date=2005 |doi=10.1002/047084289X.rt224.pub2|isbn=0-471-93623-5 }}</ref>
			] between ] and ] resulting in an organophosphonate.]]
			Reduction/deoxygenation of ] to the alcohols can also be effected using triethyl phosphite.<ref name="eEROS"/> This approach can be utilized for carbonyl α-hydroxylation by reacting the enolate with oxygen, producing an α-hydroperoxide which can be reduced by triethyl phosphite to the alcohol.<ref>{{cite journal |last1=Gardner |first1=J. N. |last2=Carlon |first2=F. E. |last3=Gnoj |first3=O. |title=One-step procedure for the preparation of tertiary α-ketols from the corresponding ketones |journal=The Journal of Organic Chemistry |date=1968 |volume=33 |issue=8 |pages=3294–3297 |doi=10.1021/jo01272a055|pmid=5742870 }}</ref> A proposed mechanism is shown below.<ref>{{cite journal |last1=Liang |first1=Yu-Feng |last2=Jiao |first2=Ning |title=Highly Efficient C–H Hydroxylation of Carbonyl Compounds with Oxygen under Mild Conditions |journal=Angewandte Chemie International Edition |date=2014 |volume=53 |issue=2 |pages=548–552 |doi=10.1002/anie.201308698|pmid=24281892 }}</ref>
			].]]
			Triethyl phosphite can also be used in the ].<ref name="eEROS"/>
			===As a ligand===
			In ] and ], triethylphosphite finds use as a ] ligand. Its complexes are generally lipophilic and feature metals in low oxidation states. Examples include the colorless complexes FeH<sub>2</sub>(P(OEt)<sub>3</sub>)<sub>4</sub> and Ni(P(OEt)<sub>3</sub>)<sub>4</sub> (m.p.&nbsp;108&nbsp;°C).<ref>{{cite book | last = Ittel | first = Steven D. | title = Inorganic Syntheses | year = 1990 | chapter = Complexes of Nickel(0) | series = ] | volume = 28 | pages = 98–104 | doi = 10.1002/9780470132593.ch26 | isbn = 978-0-470-13259-3}}</ref> It also forms a stable complex with ].<ref name="eEROS"/>
			==References==
			<references/>
			==External links==
			*
			*
			]
			]
			]