554-70-1 Usage
Description
Triethylphosphine is an organophosphorus compound with the chemical formula (C2H5)3P. It is a colorless, flammable liquid with a characteristic garlic-like odor. Triethylphosphine is a versatile reagent and ligand in various chemical reactions and processes.
Uses
Used in Suzuki Reaction:
Triethylphosphine is used as a ligand in the Suzuki reaction, a widely employed cross-coupling reaction in organic synthesis. It facilitates the formation of carbon-carbon bonds between an aryl or vinyl halide and an organoboron compound, leading to the synthesis of biaryls and other valuable compounds.
Used in Organic Synthesis:
Triethylphosphine is used as a ligand for arylation in organic synthesis. Its ability to form stable complexes with metal catalysts enhances the efficiency and selectivity of various arylation reactions, contributing to the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.
Safety Profile
Highly flammable liquid. Reactswith oxygen at low temperatures to form an explosiveproduct. When heated to decomposition it emits toxicfumes of POx.
Purification Methods
All operations should be carried out in an efficient fume cupboard because it is flammable, toxic and has a foul odour. Purify the phosphine by fractional distillation at atmospheric pressure in a stream of dry N2, as it is oxidised by air to the oxide. In 300% excess of CS2 it forms Et3PCS2 (m 118-120o crystallising from MeOH) which decomposes in CCl4 to give Et3PS as a white solid m 94o when recrystallised from EtOH. [Sorettas & Isbell J Org Chem 27 273 1962, Henderson & Streuli J Am Chem Soc 82 5791 1960, pK: Henderson & Streuli J Am Chem Soc 82 5791 1960, see also trimethylphosphine.] Store it in sealed vials under N2. Alternatively, dissolve it in Et2O and shake it with a solution of AgI and KI to form the insoluble complex. Filter off the complex, dry it over P2O5 and the Et3P is regenerated by heating the complex in a tube attached to a vacuum system. [Hewitt & Holliday J Chem Soc 530 1953, Schettas & Isbell J Org Chem 27 2573 1962, Kosolapoff Organophosphorus Compounds, Wiley p 31 1950, Beilstein 4 IV 3431.]
Check Digit Verification of cas no
The CAS Registry Mumber 554-70-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 4 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 554-70:
(5*5)+(4*5)+(3*4)+(2*7)+(1*0)=71
71 % 10 = 1
So 554-70-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H15P/c1-4-7(5-2)6-3/h4-6H2,1-3H3
554-70-1Relevant articles and documents
Clark,Wong
, p. 7073 (1977)
Rabinowitz et al.
, (1965)
Fritz,Sattler
, p. 193,218 (1975)
The Trityl-Cation Mediated Phosphine Oxides Reduction
Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric
supporting information, p. 3035 - 3043 (2021/05/10)
Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).
Method for producing alkyl phosphine
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Paragraph 0044-0059, (2020/11/23)
The invention provides a method for producing alkyl phosphine, and specifically relates to a method for producing triethyl phosphine. The method comprises the following steps: mixing hydrogen phosphide with ethylene in a solvent, adding a photocatalyst, and carrying out a reaction for 1-12 h under illumination of 20-50 W to obtain triethyl phosphine, wherein the reaction temperature being 0-50 DEGC. According to the invention, under an illumination condition, the photocatalyst easily induces a radical reaction to enhance the reaction activity of hydrogen phosphide and olefin so as to substantially improve the reaction efficiency, the rapid reaction can be performed at the room temperature and the normal pressure, the reaction time is short, the pollution and the toxicity of the catalyst are low, the toxicity of the used solvent is low compared to the toxicity of toluene and the like commonly used in the prior art, the post-treatment is relatively simple, and the yield and the purity of the product are high.