178693-20-4 Usage
Chemical structure
1,3,2-Dioxaborolane, 2,2'-[(1Z,3E)-2-phenyl-3-(phenylmethylene)-1-propene-1,3-diyl]bis[4,4,5,5-tetramethylis a complex chemical compound consisting of a dioxaborolane ring connected to a 2,2'-(1Z,3E)-2-phenyl-3-(phenylmethylene)-1-propene-1,3-diyl]bis[4,4,5,5-tetramethylgroup.
Application in organic synthesis
1,3,2-Dioxaborolane,
2,2'-[(1Z,3E)-2-phenyl-3-(phenylmethylene)-1-propene-1,3-diyl]bis[4,4,5
,5-tetramethyl- is used as a reagent for stereospecific cross-coupling reactions, which are important in the formation of carbon-carbon bonds in organic molecules.
Building block for organic compounds
It serves as a building block for the synthesis of various organic compounds, which can be used in a wide range of applications.
Pharmaceutical industry use
The compound is utilized in the pharmaceutical industry for synthesizing pharmaceutical intermediates and active pharmaceutical ingredients, which are essential for the development of new drugs.
Stereospecificity
The compound's stereospecificity allows for the selective formation of specific isomers during cross-coupling reactions, which is crucial for the synthesis of complex organic molecules with desired properties.
Reactivity
The compound's reactivity makes it a valuable tool in organic synthesis, as it can participate in various chemical reactions to form a wide range of products.
Stability
The dioxaborolane ring and the tetramethyl groups in the compound provide stability to the molecule, making it suitable for use in various chemical reactions and applications.
Check Digit Verification of cas no
The CAS Registry Mumber 178693-20-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,8,6,9 and 3 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 178693-20:
(8*1)+(7*7)+(6*8)+(5*6)+(4*9)+(3*3)+(2*2)+(1*0)=184
184 % 10 = 4
So 178693-20-4 is a valid CAS Registry Number.
178693-20-4Relevant academic research and scientific papers
Zirconocene-mediated preparation of 1,3-, 1,4-, and 2,3-dibora-1,3-butadienes: Their isolation and characterization and use in Suzuki-Miyaura coupling
Desurmont, Guillaume,Klein, Rita,Uhlenbrock, Stefan,Lalo?, Eric,Deloux, Laurent,Giolando, Dean M.,Kim, Yong Wah,Pereira, Schubert,Srebnik, Morris
, p. 3323 - 3328 (2008/10/08)
Hydrozirconation of 1-alkynyl pinacolboronates, 1, with HZrCp2Cl provides gem-borazirconocenes 2. The latter when treated with CuBr gives the homocoupled (1E,3E)-2,3-dibora-1,3-butadienes, 3, in good yield (62-67%). The reaction works even for hindered 2 (R = t-Bu). Structure 3 was assigned on the basis of NMR. Suzuki-Miyaura coupling of 3a (R = n-Bu) with PhI in the presence of CsF leads to the replacement of both boron groups by phenyl and hydrogen to give 6 in 76% yield. Zirconocene-mediated coupling of 1 leads to diastereomeric products: (1E,3E)-1,3-dibora-1,3-butadienes, 4, in 7-26% isolated yields and (1E,3E)-1,4-dibora-1,3-butadienes, 5, in 17-34% isolated yields. The two isomers can be separated by selective precipitation of 5 from the reaction mixture in pentane (-20 °C) followed by silica gel chromatography to give pure 4. The reaction does not work when R in 1 is the t-Bu group. Assignments of structures for 4 and 5 were done on the basis of 1D and 2D NMR experiments. In addition, a single-crystal X-ray analysis of 5a showed it to be a highly planar and linearly oriented molecule. Suzuki-Miyaura coupling of 4a proceeded to replace the terminal boron group exclusively, while the internal boron group of 4a remained intact.
