Triethyl phosphite

Triethyl phosphite
Names
Preferred IUPAC name
Triethyl phosphite
Other names
Triethoxyphosphine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.139 Edit this at Wikidata
UNII
  • InChI=1S/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3 checkY
    Key: BDZBKCUKTQZUTL-UHFFFAOYSA-N checkY
  • InChI=1/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3
    Key: BDZBKCUKTQZUTL-UHFFFAOYAP
  • O(P(OCC)OCC)CC
Properties
C6H15O3P
Molar mass 166.157 g·mol−1
Appearance colorless liquid
Density 0.969 g/mL
Melting point −70 °C (−94 °F; 203 K)
Boiling point 156 °C (313 °F; 429 K) (57 to 58 °C at 16 mm)
Solubility soluble in most organic solvents
-104.8·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Triethyl phosphite (TEP) 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.

The molecule features a pyramidal phosphorus(III) center bound to three ethoxide groups. Its 31P NMR spectrum features a signal at around +139 ppm vs phosphoric acid standard.

Triethylphosphite is prepared by treating phosphorus trichloride with ethanol in the presence of a base, typically a tertiary amine:[1]

PCl3 + 3 EtOH + 3 R3N → P(OEt)3 + 3 R3NH + 3 Cl−

In the absence of the base, the reaction of ethanol and phosphorus trichloride affords diethylphosphite ((EtO)2P(O)H). Of the many related compounds can be prepared similarly, triisopropyl phosphite is an example (b.p. 43.5 °C/1.0 mm; CAS# 116-17-6).

Reactions

Triethyl phosphite can react with electrophiles in a Michaelis–Arbuzov reaction to produce organophosphonates. For example, the reaction between triethyl phosphite and ethyl bromoacetate produces a phosphonate suitable for use in the Horner–Wadsworth–Emmons reaction.[2]

Michaelis–Arbuzov reaction between ethyl bromoacetate and triethyl phosphite resulting in an organophosphonate.
Michaelis–Arbuzov reaction between ethyl bromoacetate and triethyl phosphite resulting in an organophosphonate.

Reduction/deoxygenation of hydroperoxides to the alcohols can also be effected using triethyl phosphite.[2] 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.[3] A proposed mechanism is shown below.[4]

Reaction scheme and proposed mechanism for carbonyl α-hydroxylation using oxygen and triethyl phosphite.
Reaction scheme and proposed mechanism for carbonyl α-hydroxylation using oxygen and triethyl phosphite.

Triethyl phosphite can also be used in the Corey–Winter olefin synthesis.[2]

As a ligand

In coordination chemistry and homogeneous catalysis, triethylphosphite finds use as a soft ligand. Its complexes are generally lipophilic and feature metals in low oxidation states. Examples include the colorless complexes FeH2(P(OEt)3)4 and Ni(P(OEt)3)4 (m.p. 108 °C).[5] It also forms a stable complex with copper(I) iodide.[2]

References

  1. ^ Ford-Moore, A. H.; Perry, B. J. (1951). "Triethyl Phosphite". Org. Synth. 31: 111. doi:10.15227/orgsyn.031.0111.
  2. ^ a b c d Piscopio, Anthony D.; Shakya, Sagar (2005). "Triethyl Phosphite". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt224.pub2. ISBN 0-471-93623-5.
  3. ^ Gardner, J. N.; Carlon, F. E.; Gnoj, O. (1968). "One-step procedure for the preparation of tertiary α-ketols from the corresponding ketones". The Journal of Organic Chemistry. 33 (8): 3294–3297. doi:10.1021/jo01272a055. PMID 5742870.
  4. ^ Liang, Yu-Feng; Jiao, Ning (2014). "Highly Efficient C–H Hydroxylation of Carbonyl Compounds with Oxygen under Mild Conditions". Angewandte Chemie International Edition. 53 (2): 548–552. doi:10.1002/anie.201308698. PMID 24281892.
  5. ^ Ittel, Steven D. (1990). "Complexes of Nickel(0)". Inorganic Syntheses. Inorganic Syntheses. Vol. 28. pp. 98–104. doi:10.1002/9780470132593.ch26. ISBN 978-0-470-13259-3.

Read other articles:

مارسيلو باروفيرو

مارسيلو باروفيرو   معلومات شخصية الميلاد 18 فبراير 1984 (العمر 40 سنة) الطول 1.82 م (5 قدم 11 1⁄2 بوصة) مركز اللعب حارس مرمى الجنسية الأرجنتين  معلومات النادي النادي الحالي أتليتكو سان لويس الرقم 1 المسيرة الاحترافية1 سنوات فريق م. (هـ.) 2003–2007 أتليتيكو رافائيلا 117 (0) 2...

 

Daftar Eparki dan Metropolitan Gereja Ortodoks Rusia

Rusia Eparki dan metropolitan Gereja Ortodoks Rusia di Federasi Rusia:[1] Organisasi Gereja Ortodoks Rusia Eparki Tahta Didirikan Situs resmi Metropolitan Tahta Dibentuk Barnaul Barnaul 1930 [1] Diarsipkan 2011-06-09 di Wayback Machine. Altai Barnaul 2015 Biysk Biysk 1919 Rubtsovsk Rubtsovsk 2015 Slavgorod Slavgorod 2015 Arkhangelsk dan Kholmogory Arkhangelsk 1628 [2] Arkhangelsk Arkhangelsk 2011 Kotlas dan Velsk Kotlas 2011 [3] Naryan-Mar Naryan-Mar 2011 [4] Akhtubinsk Akhtubinsk 201...

 

كتاب جوتنبرج السنوي

هذه المقالة يتيمة إذ تصل إليها مقالات أخرى قليلة جدًا. فضلًا، ساعد بإضافة وصلة إليها في مقالات متعلقة بها. (يونيو 2020) كتاب جوتنبرج السنوي كتاب جوتنبرج السنوي عنوان مختصر (أيزو 4) Gutenberg-Jahrb. الموضوع تاريخ الطباعة اللغة متعدد اللغات المحررون Stephan Füssel تفاصيل النشر الناشر Internationale...

Kwon Mina

Ini adalah nama Korea; marganya adalah Kwon. MinaKwon Mina pada acara jumpa fans untuk Red Motion di Bandara Gimpo, Oktober 2013Nama asal권민아LahirKwon Mina21 September 1993 (umur 30)Busan, South KoreaPekerjaan Penyanyi aktris Tinggi160 cm (5 ft 3 in) (2015)[1]Berat43 kg (95 pon) (95 pon) (2015)[1]Karier musikGenre K-pop Instrumen Vokal gitar bass Tahun aktif2012–sekarangLabel FNC Entertainment CJ E&M Music and Live Artis terkait AO...

 

Uffenheim

Uffenheim Lambang kebesaranLetak Uffenheim NegaraJermanNegara bagianBayernWilayahMittelfrankenKreisNeustadt an der Aisch-Bad WindsheimMunicipal assoc.Uffenheim Subdivisions8 ortsteilPemerintahan • MayorGeorg Schöck (FWG)Luas • Total59,47 km2 (2,296 sq mi)Ketinggian329 m (1,079 ft)Populasi (2013-12-31)[1] • Total6.195 • Kepadatan1,0/km2 (2,7/sq mi)Zona waktuWET/WMPET (UTC+1/+2)Kode pos97215Kode area tel...

 

Domoprednate

Chemical compound DomoprednateClinical dataTrade namesStermonidOther namesRo 12-7024; 11β-Hydroxy-D-homopregna-1,4-diene-3,20-dione 17α-butyrateRoutes ofadministrationTopicalDrug classCorticosteroid; GlucocorticoidIdentifiers IUPAC name [(1R,4aS,4bS,10aR,10bS,11S,12aS)-1-Acetyl-11-hydroxy-10a,12a-dimethyl-8-oxo-2,3,4,4a,4b,5,6,10b,11,12-decahydrochrysen-1-yl] butanoate CAS Number66877-67-6PubChem CID68868ChemSpider62100UNII910G0QIM2MChEMBLChEMBL2106538ECHA InfoCard100.060.441 Chemical and p...

العلاقات الدنماركية البليزية

العلاقات الدنماركية البليزية الدنمارك بليز   الدنمارك   بليز تعديل مصدري - تعديل   العلاقات الدنماركية البليزية هي العلاقات الثنائية التي تجمع بين الدنمارك وبليز.[1][2][3][4][5] مقارنة بين البلدين هذه مقارنة عامة ومرجعية للدولتين: وجه المقارنة...

 

List of Paris Saint-Germain F.C. (women) records and statistics

PSG's team during the 2013–14 season. Paris Saint-Germain Football Club have won four titles. Domestically, the capital side have clinched one Division 1 championship, three French Cups and one Division 2 title. In international club football, Paris have reached the UEFA Champions League final twice (2015 and 2017). Additionally, PSG have won one unofficial title. Influential officials and players in the club's history include most decorated president Nasser Al-Khelaifi, trophy-winning man...

 

Cornelis Drebbel

Dutch engineer and inventor Cornelis DrebbelPortrait of Drebbel, c. 1631Born1572Alkmaar, Habsburg Netherlands, Holy Roman EmpireDied7 November 1633(1633-11-07) (aged 60–61)London, EnglandEducationHendrick GoltziusOccupation(s)Engineer, inventorSpouse Sophia Jansdochter Goltzius ​ ​(m. 1595)​Children6 Cornelis Jacobszoon Drebbel[1] (Dutch pronunciation: [kɔrˈneːlɪ ˈʃaːkɔbzoːn ˈdrɛbəl];[a] 1572 – 7 November 1633) wa...

Simon Gagné

Questa voce sull'argomento hockeisti su ghiaccio canadesi è solo un abbozzo. Contribuisci a migliorarla secondo le convenzioni di Wikipedia. Segui i suggerimenti del progetto di riferimento. Simon Gagné Nazionalità  Canada Altezza 185 cm Peso 89 kg Hockey su ghiaccio Ruolo Attaccante Tiro Sinistro Termine carriera 2015 Carriera Periodo Squadra PG G A Pt Giovanili 1995-1996 Sainte-Foy Gouverneurs 43 20 17 37 1996-1997  Beauport Harfangs 51 9 22 31 1997-1999  Québec Rem...

 

Гуань Юй

В этом китайском имени фамилия (Гуань) стоит перед личным именем. Гуань Юй Дата рождения 160 Место рождения Яньху, округ Хэдун[d], Империя Хань Дата смерти январь 220 Место смерти Линьцзюй, провинция Цзинчжоу Страна Восточная Хань[d] Род деятельности офицер, армей�...

 

2020年夏季奧林匹克運動會柔道比賽

第三十二届夏季奥林匹克运动会柔道比賽比賽場館日本武道館日期2021年7月24日至31日項目數15参赛选手393（含未上场5人）位選手，來自128（含未上场4队）個國家和地區← 20162024 → 2020年夏季奥林匹克运动会柔道比赛个人男子女子60公斤级48公斤级66公斤级52公斤级73公斤级57公斤级81公斤级63公斤级90公斤级70公斤级100公斤级78公斤级100公斤以上级78公斤以上级团体混...

مزولة

ساعة شمسية (مزولة) موجودة على حائط الجانب الأيمن من مسجد مهرماه سلطان (1548م) بأسكدار باسطنبول لبيان وقت صلاة الظهر وصلاة العصر. مكتوب أعلى المزولة بالتركية الحديثة: «تحديد أوقات الظهر والعصر بواسطة الظل بحسب الشهر القمري». 50°25′23″N 6°12′06″E / 50.4231°N 6.2017°E / 50.4231; 6.2017...

 

Weltschmerz

German word for deep sadness about the state of the world For the Canadian comic strip, see Weltschmerz (comic strip). Engraving by Jusepe de Ribera depicting the melancholic and world-weary figure of a poet. Weltschmerz (German: [ˈvɛltʃmɛɐ̯ts] ⓘ; literally world-pain) is a literary concept describing the feeling experienced by an individual who believes that reality can never satisfy the expectations of the mind,[1][2] resulting in a mood of weariness or sadne...

 

Arch-Treasurer

Arms of the office of Arch-Treasurer of the Holy Roman Empire, showing the imperial crown Arms of the electorate of Brunswick-Lüneburg, with the Arch-Treasurer's crown at centre. An Arch-Treasurer (German: Erzschatzmeister, Latin: Archithesaurarius) is a chief treasurer, specifically the great treasurer of the Holy Roman Empire. The title of Arch-Treasurer was only ceremonially significant, as it was only used in the coronation of Emperors.[1] History During the 30 Years' War, Freder...

ぷよぷよ

この項目では、パズルゲームシリーズの第1作について説明しています。 シリーズ全体については「ぷよぷよシリーズ」をご覧ください。 この作品の同名モンスターについては「ぷよぷよ (ゲームキャラクター)」をご覧ください。 『ぷよぷよ』（Puyo Puyo）は、コンパイルが開発し、1991年10月25日に徳間書店インターメディアから発売された落ち物パズルゲーム。また、�...

 

何鏡堂

何鏡堂出生1938年4月（86歲） 中國廣東省第一行政督察區東莞縣石龍鎮国籍 中华人民共和国母校華南工學院职业建筑师建筑 西漢南越王博物館 浙江大學紫金港校區 安徽师范大学花津校区 华南师范大学南海校区 中國2010年上海世界博覽會中國館等 项目 侵华日军南京大屠杀遇难同胞纪念馆擴建工程 何鏡堂（1938年4月—），廣東東莞人，中國當代建築師，现任华南理工�...

 

Carlos Vicente Robles

Carlos VicenteNazionalità Spagna Altezza179 cm Calcio RuoloAttaccante Squadra Alavés CarrieraGiovanili 2013-2017Stadium Casablanca2017-2018 Real Saragozza Squadre di club1 2017-2020 Real Saragozza B68 (14)2020-2021 Pobla Mafumet1 (0)2021 Ejea18 (4)2021-2022 Calahorra37 (11)2022-2024 Racing Ferrol61 (12)2024- Alavés5 (0) 1 I due numeri indicano le presenze e le reti segnate, per le sole partite di campionato.Il simbolo → indica un trasferimento...

Thomas Leiper Estate

Historic house in Pennsylvania, United States United States historic placeThomas Leiper EstateU.S. National Register of Historic Places Avondale, Thomas Leiper HouseShow map of PennsylvaniaShow map of the United StatesLocationAvondale Rd., Wallingford, PennsylvaniaCoordinates39°53′12″N 75°21′30″W / 39.88667°N 75.35833°W / 39.88667; -75.35833Area6 acres (2.4 ha)Built1785NRHP reference No.70000547[1]Added to NRHPDecember 29, 1970 The Th...

 

Shlomo Gazit

Shlomo GazitShlomo GazitNama asalשלמה גזיתLahirShlomo Weinstein1926 (1926)Istanbul, TurkiMeninggal8 Oktober 2020(2020-10-08) (umur 93–94)Dikenal atas Mayor Jenderal dalam Pasukan Pertahanan Israel; mengepalai Direktorat Intelijensi Militer Israel Presiden Universitas Ben-Gurion Kepala Agensi Yahudi KerabatMordechai Gazit (saudara) Shlomo Gazit (bahasa Ibrani: שלמה גזית‎; 1926 – 8 Oktober 2020) adalah seorang perwira militer dan akademisi asal Isra...