53317-09-2 Usage
Uses
Used in Organic Synthesis:
BETA-BENZYL-9-BBN is used as a reagent for the formation of carbon-carbon bonds, facilitating the efficient and selective transfer of a diene unit to various organic molecules. This function is vital in the synthesis of a wide array of compounds, including those in pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Development:
In the pharmaceutical industry, BETA-BENZYL-9-BBN is utilized as a key intermediate in the synthesis of complex drug molecules. Its ability to form carbon-carbon bonds and its compatibility with various organic molecules make it an indispensable tool in the development of new medications.
Used in Agrochemical Production:
Similarly, in agrochemicals, BETA-BENZYL-9-BBN serves as a critical component in the synthesis of pesticides and other crop protection agents. Its reactivity and selectivity contribute to the creation of effective and targeted agrochemicals.
Used in Materials Science:
In the field of materials science, BETA-BENZYL-9-BBN is employed as a reagent for the synthesis of advanced materials with specific properties. Its role in creating carbon-carbon bonds is crucial for the development of new materials with tailored characteristics for various applications.
Used in Asymmetric Catalysis:
BETA-BENZYL-9-BBN is also used as a catalyst in asymmetric reactions, a significant area of research in organic chemistry. Its unique structure and reactivity allow for the selective formation of enantiomers, which is essential in the synthesis of chiral compounds with specific biological activities.
Used in the Creation of Complex Organic Molecules:
Lastly, BETA-BENZYL-9-BBN is applied in the synthesis of complex organic molecules, where its ability to transfer diene units and form carbon-carbon bonds is invaluable. This application is particularly relevant in the development of novel organic compounds with unique structures and properties.
Check Digit Verification of cas no
The CAS Registry Mumber 53317-09-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,3,1 and 7 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 53317-09:
(7*5)+(6*3)+(5*3)+(4*1)+(3*7)+(2*0)+(1*9)=102
102 % 10 = 2
So 53317-09-2 is a valid CAS Registry Number.
InChI:InChI=1/C15H21B/c1-2-6-13(7-3-1)12-16-14-8-4-9-15(16)11-5-10-14/h1-3,6-7,14-15H,4-5,8-12H2
53317-09-2Relevant academic research and scientific papers
Synthesis of alcohols from m-fluorophenylsulfones and dialkylboranes: Application to the C14-C35 building block of E7389
Liu, Lei,Henderson, James A.,Yamamoto, Akihiko,Bremond, Paul,Kishi, Yoshito
, p. 2262 - 2265 (2012/06/30)
The reaction of m-fluorophenylsulfone anions with dialkylboranes, followed by alkaline hydroperoxide oxidation, yields alcohols in high yields. Optimization of the process, scope and limitation, and application to the synthesis of one of the C14-C35 building blocks of E7389, a right half analogue of halichondrin B, are reported.
Asymmetric sulfur ylide reactions with boranes: Scope and limitations, mechanism and understanding
Fang, Guang Y.,Wallner, Olov A.,Di Blasio, Nadia,Ginesta, Xavier,Harvey, Jeremy N.,Aggarwal, Varinder K.
, p. 14632 - 14639 (2008/09/17)
The reactions of aryl-stabilized sulfur ylides with organoboranes has been studied under a variety of conditions. At 5 or -78°C, the reaction with Et3B gave a mixture of the first and second homologation products, but at -100°C, only the first homologation product was obtained even with just 1.1 equiv of Et3B. Under these optimized conditions, the chiral sulfur ylides (derived from camphor sulfonic acid) with different aryl groups were reacted with Et3B to give the corresponding alcohols (95-98% yield, 96-98% ee) and amines (74-77% yield, >98% ee). The origin of the high enantioselectivity is discussed. The use of nonsymmetrical 9-BBN derivatives was also explored. It was found that whereas primary alkyl substituents gave mixtures of products derived from competing migration of the boron substituent and the boracycle, all other groups resulted in either exclusive migration of the boron substituent (Ph, hexenyl, i-Pr) or exclusive migration of the boracycle (hexynyl, cyclopropyl). The factors responsible for the outcome of the reactions involving a hindered (i-Pr) and an unhindered (propynyl) substituent were studied by DFT calculations. This revealed that, in the case of an unhindered substituent, the conformation of the ate complex is the dominant factor whereas, in the case of a hindered substituent, the barriers to interconversion between the conformers of the ate complex and subsequent migration control the outcome of the reaction.
