Differentiation of symmetrical diols by reduction of the corresponding cyclic acetals with 9-BBN. Selective hydroboration reduction reagent. Protecting group for alkenes Reactant for: • Linear SPPS synthesis of ubiquitin derivatives • Copper-catalyzed cross-coupling reactions of organoboron compounds with primary alkyl halides and pseudohalides • Intramolecular insertion of alkenes into palladium-nitrogen bonds • Preparation of (phosphonoacetyl)ornithine to study effect on arginine biosynthetic genes in yeast • Hetero-Diels-Alder reaction for synthesis of spirocyclic alkaloids
9-Borabicyclo[3.3.1]nonane is an organic compound, which is generally used as a hydroborating agent. It is thermally stable, less sensitive to oxygen and water when compared to other dialkyl boranes. It is commonly used to prepare aldehydes from alkynes.
application：
9-BBN monomer acts as a selective hydroboration reagent in synthetic organic chemistry. It is employed in Suzuki reactions as well as in the preparation of terminal alcohols by the region selective addition of alkenes followed by oxidative cleavage using hydrogen peroxide. It is also used in copper-catalyzed cross-coupling reactions of organoboron compounds with primary alkyl halides and pseudohalides. It acts as a protecting group for alkenes. Further, it is used as a reactant for Hetero-Diels-Alder reaction for the synthesis of spirocyclic alkaloids. In addition to this, it is used in intramolecular insertion of alkenes into palladium-nitrogen bonds.
Miscible with ether, hexane, benzene, toluene, carbon tetrachloride, chloroform, dimethylsulfide and dichloromethane. Slightly miscible with cyclohexane, dimethoxyethane, diglyme and dioxane.
1.Kun Zhang, Xiaoni Wang, Minggang Tian, Zhiming Gou, Yujing Zuo. (2021) The diversity of the coordination bond generated a POSS-based fluorescent probe for the reversible detection of Cu(II), Fe(III) and amino acids. Journal of Materials Chemistry B, 9 (47):(9744-9753). [PMID:34787631]
References
1.Zhishan Bo,Jun Qiu,Jing Li,A Dieter Schlüter. (2004-02-28) Synthesis of aryl/alkyl building blocks for dendrimer and hyperbranched polymer synthesis.. Organic letters, 6 ((5)):(667-669). [PMID:14986945]
2.Yi Luan,Scott E Schaus. (2011-04-09) Multicomponent Mannich reactions with boron enolates derived from diazo esters and 9-BBN.. Organic letters, 13 ((9)):(2510-2513). [PMID:21473584]
3.Kun Zhang, Xiaoni Wang, Minggang Tian, Zhiming Gou, Yujing Zuo. (2021) The diversity of the coordination bond generated a POSS-based fluorescent probe for the reversible detection of Cu(II), Fe(III) and amino acids. Journal of Materials Chemistry B, 9 (47):(9744-9753). [PMID:34787631]
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