9-Borabicyclo[3.3.1]nonane - 0.5 M in THF , CAS No.280-64-8

CAS: 280-64-8 Cat. No.: B130058 Molecular Weight: 122.02 Beilstein Registry Number: 605509 EC Number: 206-000-9 PubChem CID: 6327450

GRADE & PURITY 0.5 M in THF

Synonyms

AKOS015833689 | 9-borabicyclo [3.3,1 ]nonane | 9-borabicyclo[3, 3,1]nonane | EINECS 206-000-9 | DTXSID10167572 | FT-0657566 | Q-101083 | 1,1-diallyl-2-oxohydrazine | 9-Borabicyclo(3.3.1)nonane | 1H-Indole-3-acetic acid, 1-benzoyl-2-methyl- | 9-BBN

Storage

Room temperature,Argon charged

Shipped In

Normal

Overview

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.

Specifications

Synonyms

AKOS015833689 | 9-borabicyclo [3.3, 1 ]nonane | 9-borabicyclo[3, 3, 1]nonane | EINECS 206-000-9 | DTXSID10167572 | FT-0657566 | Q-101083 | 1, 1-diallyl-2-oxohydrazine | 9-Borabicyclo(3.3.1)nonane | 1H-Indole-3-acetic acid, 1-benzoyl-2-methyl- | 9-BBN

Specifications & Purity

0.5 M in THF

Storage

Room temperature, Argon charged

Shipped In

Normal

Names and Identifiers

• Pubchem Sid: 504764050
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764050
• Canonical Smiles: [B]1C2CCCC1CCC2
• InChIKey: AMKGKYQBASDDJB-UHFFFAOYSA-N
• INCHI: 1S/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2
• Isomeric SMILES: [B]1C2CCCC1CCC2
• WGK Germany: 3
• PubChem CID: 6327450
• Molecular Weight: 122.02
• Beilstein: 605509

Chemical and Physical Properties

• Solubility: Miscible with ether, hexane, benzene, toluene, carbon tetrachloride, chloroform, dimethylsulfide and dichloromethane. Slightly miscible with cyclohexane, dimethoxyethane, diglyme and dioxane.
• Sensitivity: Air & Moisture Sensitive
• Flash Point(°F): -2°F
• Flash Point(°C): -19℃
• Molecular Weight: 121.010 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 121.119 Da
• Monoisotopic Mass: 121.119 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 80.700
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

References

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] [10.1039/D1TB01947C]

2. HuaQing Liang, QiHua Zhou, YongJiang Long, WanChu Wei, Shuo Feng, GuoDong Liang, FangMing Zhu.  (2018)  Synthesis and self-assembly of a novel amphiphilic diblock copolymer consisting of isotactic polystyrene and 1,4-trans-polybutadiene-graft-poly(ethylene oxide).  RSC Advances,  8  (23): (12752-12759).  [PMID:35541237] [10.1039/C8RA01288A]