7688-25-7 Usage
Description
1,4-Bis(diphenylphosphino)butane, also known as a phosphine ligand, is an organic compound that exists as a white to light yellow crystal powder. It is characterized by its phosphorus atoms bonded to two phenyl groups and a butane chain, which contributes to its unique chemical properties and reactivity.
Uses
1,4-Bis(diphenylphosphino)butane is used as a ligand in various chemical reactions and applications due to its ability to form stable complexes with metal catalysts, enhancing their performance and selectivity.
Used in Organometallic Chemistry:
1,4-Bis(diphenylphosphino)butane is used as a ligand for alkylations, isomerization reactions, and other organometallic chemistry applications. Its presence improves the efficiency and selectivity of these reactions, making it a valuable component in the synthesis of various organic compounds.
Used in Cross-Coupling Reactions:
1,4-Bis(diphenylphosphino)butane is used as a ligand in Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds. It plays an essential role in palladium(0)-catalyzed acylcyanation of arylacetylenes and deprotection of allyloxycarbamates, contributing to the formation of complex molecular structures.
Used in Heck Reaction:
In the Heck reaction, 1,4-Bis(diphenylphosphino)butane acts as a ligand, facilitating the formation of carbon-carbon bonds through the coupling of aryl or vinyl halides with alkenes in the presence of a palladium catalyst.
Used in Negishi Coupling:
1,4-Bis(diphenylphosphino)butane is used as a ligand in Negishi coupling, a cross-coupling reaction that involves the formation of carbon-carbon bonds between an organozinc reagent and an organic electrophile, such as an aryl or vinyl halide.
Used in Sonogashira Coupling:
In Sonogashira coupling, 1,4-Bis(diphenylphosphino)butane serves as a ligand, promoting the formation of carbon-carbon bonds between an aryl or vinyl halide and a terminal alkyne in the presence of a palladium catalyst.
Overall, 1,4-Bis(diphenylphosphino)butane is a versatile and essential ligand in various chemical reactions and applications, particularly in organometallic chemistry and cross-coupling reactions, due to its ability to enhance the performance and selectivity of metal catalysts.
Purification Methods
Recrystallise it from EtOH [Trippett J Chem Soc 4263 1961]. [King J Coord Chem 1 62 1971, Tolman Chem Rev 77 313 1977.]
Check Digit Verification of cas no
The CAS Registry Mumber 7688-25-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,6,8 and 8 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 7688-25:
(6*7)+(5*6)+(4*8)+(3*8)+(2*2)+(1*5)=137
137 % 10 = 7
So 7688-25-7 is a valid CAS Registry Number.
InChI:InChI=1/C28H28P2/c1-5-15-25(16-6-1)29(26-17-7-2-8-18-26)23-13-14-24-30(27-19-9-3-10-20-27)28-21-11-4-12-22-28/h1-12,15-22H,13-14,23-24H2
7688-25-7Relevant articles and documents
Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium
Ling, Liang,Luo, Meiming,Tang, Jinghua,Yuan, Shuqing,Zeng, Xiaoming
, p. 1581 - 1586 (2022/03/14)
We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)-P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechani
Bisphosphine catalyzed sequential [3 + 2] cycloaddition and Michael addition of ynones with benzylidenepyrazolones: Via dual α′,α′-C(sp3)-H bifunctionalization to construct cyclopentanone-fused spiro-pyrazolones
Zhang, Jiayong,Miao, Zhiwei
supporting information, p. 9461 - 9471 (2019/01/03)
A bisphosphine-catalyzed sequential [3 + 2] cycloaddition and Michael addition reaction of ynones with benzylidenepyrazolones has been developed. Under the catalysis of DPPB [1,4-bis(diphenylphosphino)butane], the reaction proceeded smoothly to give spiro-[cyclopentanone] pyrazolone derivatives in moderate to good yields with good diastereoselectivities via sequential dual α′,α′-C(sp3)-H bifunctionalization annulation. This strategy provides a novel route toward the synthesis of spiro-[cyclopentanone] pyrazolones containing three contiguous stereocenters which possess potential pharmaceutical activities.
A catalytic method for the reduction of secondary and tertiary phosphine oxides
Berthod, Mika?l,Favre-Réguillon, Alain,Mohamad, Jahjah,Mignani, Gérard,Docherty, Gordon,Lemaire, Marc
, p. 1545 - 1548 (2008/02/05)
TMDS has been found to be an efficient hydride source for the reduction of tertiary and secondary phosphine oxides using a catalytic amount of Ti(Oi-Pr)4. All classes of tertiary phosphine oxides, such as triaryl, trialkyl, and diphosphine, were effectively reduced. Georg Thieme Verlag Stuttgart.