1663-45-2 Usage
Description
1,2-Bis(diphenylphosphino)ethane, also known as 1,2-Ph2PC2H4PPh2, is a white to light yellow crystalline powder that serves as a bidendate ligand in coordination chemistry. It is widely used in the preparation of metal complexes and plays a crucial role in various chemical reactions due to its unique properties.
Uses
1. Used in the Suzuki Reaction:
1,2-Bis(diphenylphosphino)ethane is used as a ligand in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds. Its use in this reaction enhances the efficiency and selectivity of the process.
2. Used in Coordination Chemistry:
As a bidendate ligand, 1,2-Bis(diphenylphosphino)ethane is used in coordination chemistry to prepare metal complexes. These complexes are essential in various catalytic processes and have applications in different industries.
3. Used in Allylic Alkylation and Decarboxylation:
1,2-Bis(diphenylphosphino)ethane is used as a ligand in the metal-catalyzed allylic alkylation and decarboxylation of allylic esters. These reactions are vital in the synthesis of various organic compounds and pharmaceuticals.
4. Used in 1,3-Diene Synthesis:
This ligand is also employed in the synthesis of 1,3-dienes, which are important building blocks in organic chemistry and have applications in the production of various chemicals and materials.
5. Used in Cycloaddition Reactions:
1,2-Bis(diphenylphosphino)ethane is used in cycloaddition reactions, which are essential for the formation of cyclic compounds. These reactions are widely used in the synthesis of complex organic molecules and pharmaceuticals.
6. Used in Carbonylation Reactions:
This ligand is also used in carbonylation reactions, which involve the introduction of a carbonyl group into a molecule. Carbonylation reactions are crucial in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
7. Used in the Preparation of Bis(dicyclohexylphosphino)ethane:
1,2-Bis(diphenylphosphino)ethane is used to prepare bis(dicyclohexylphosphino)ethane by hydrogenation. The resulting compound is another valuable ligand with applications in coordination chemistry and catalysis.
Purification Methods
Recrystallise it from aqueous EtOH or *C6H6. The dimethiodide, when recrystallised from MeOH has m 305-307o, and the dioxide when recrystallised from toluene or DMF (needles), or *C6H6 (plates) has m 252-254o (276-278o) [Isslieb et al. Chem Ber 92 3175 1959, NMR: Aquiar et al. J Org Chem 29 1660 1964, B.ckvall et al. J Org Chem 52 5430 1987]. [Beilstein 16 IV 958.]
Check Digit Verification of cas no
The CAS Registry Mumber 1663-45-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,6 and 3 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1663-45:
(6*1)+(5*6)+(4*6)+(3*3)+(2*4)+(1*5)=82
82 % 10 = 2
So 1663-45-2 is a valid CAS Registry Number.
InChI:InChI=1/C26H24P2/c1-22(27(23-14-6-2-7-15-23)24-16-8-3-9-17-24)28(25-18-10-4-11-19-25)26-20-12-5-13-21-26/h2-22H,1H3
1663-45-2Relevant articles and documents
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Poulin et al.
, p. 87,88-92 (1975)
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King et al.
, p. 2353,2354 (1968)
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Schindlbauer,Hilzensauer
, p. 961,963, 964 (1965)
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Zingales,Graziani,Belluco
, p. 256 (1967)
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Cardaci, G.,Murgia, S. M.
, p. 222 - 226 (1972)
A mild and efficient CsOH-promoted synthesis of ditertiary phosphines
Honaker, Matthew T.,Salvatore, Ralph Nicholas
, p. 277 - 283 (2004)
A mild and efficient method for the synthesis of ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves, and DMF, various dihalides were coupled with diphenylphosphine at room temperature, and the results have demonstrated that this methodology offers a general synthetic procedure producing a variety of ditertiary phosphines in high yields.
A Mild One-Pot Reduction of Phosphine(V) Oxides Affording Phosphines(III) and Their Metal Catalysts
Kapu?niak, ?ukasz,Plessow, Philipp N.,Trzybiński, Damian,Wo?niak, Krzysztof,Hofmann, Peter,Jolly, Phillip Iain
, p. 693 - 701 (2021/04/06)
The metal-free reduction of a range of phosphine(V) oxides employing oxalyl chloride as an activating agent and hexachlorodisilane as reducing reagent has been achieved under mild reaction conditions. The method was successfully applied to the reduction of industrial waste byproduct triphenylphosphine(V) oxide, closing the phosphorus cycle to cleanly regenerate triphenylphosphine(III). Mechanistic studies and quantum chemical calculations support the attack of the dissociated chloride anion of intermediated phosphonium salt at the silicon of the disilane as the rate-limiting step for deprotection. The exquisite purity of the resultant phosphine(III) ligands after the simple removal of volatiles under reduced pressure circumvents laborious purification prior to metalation and has permitted the facile formation of important transition metal catalysts.
Preparation technology of bis(dibenzyl)phosphorane
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Paragraph 0015, (2019/08/06)
The invention provides a preparation technology of bis(dibenzyl)phosphorane and belongs to the technical field of synthesis of organic matters. The technology comprises the following steps: taking metallic lithium, triphenylphosphine and water to react to generate dibenzylphosphorane; taking the dibenzylphosphorane to react with dihalogenohydrocarbon to generate the bis(dibenzyl)phosphorane. According to a production technology, an intermediate product and an intermediate byproduct do not need to be separated; the technology is simple in technological operation, low in raw material cost and high in yield and can be used for producing the low-cost and high-quality bis(dibenzyl)phosphorane.