280-64-8 Usage
Description
9-Borabicyclo[3.3.1]nonane, commonly known as 9-BBN, is an organic compound that serves as a versatile hydroborating agent in various chemical reactions. It is a white crystalline powder, known for its thermal stability and reduced sensitivity to oxygen and water compared to other dialkyl boranes. 9-BBN is widely utilized in synthetic organic chemistry for a range of applications, including the preparation of aldehydes from alkynes.
Uses
Used in Synthetic Organic Chemistry:
9-Borabicyclo[3.3.1]nonane is used as a selective hydroboration reagent for the region-selective addition of alkenes, followed by oxidative cleavage using hydrogen peroxide. This process is crucial in the synthesis of various organic compounds.
Used in Suzuki Reactions:
In the field of cross-coupling reactions, 9-BBN is employed in Suzuki reactions, which are widely used for the formation of carbon-carbon bonds, particularly in the synthesis of complex organic molecules.
Used as a Protecting Group for Alkenes:
9-Borabicyclo[3.3.1]nonane acts as a protecting group for alkenes, preventing unwanted reactions and ensuring the selective formation of desired products.
Used in Copper-Catalyzed Cross-Coupling Reactions:
9-BBN is utilized in copper-catalyzed cross-coupling reactions of organoboron compounds with primary alkyl halides and pseudohalides, further expanding its applications in synthetic organic chemistry.
Used in Hetero-Diels-Alder Reaction:
9-Borabicyclo[3.3.1]nonane is used as a reactant in the Hetero-Diels-Alder reaction, which is essential for the synthesis of spirocyclic alkaloids, a class of biologically active compounds.
Used in Intramolecular Insertion of Alkenes:
9-BBN is employed in the intramolecular insertion of alkenes into palladium-nitrogen bonds, a key step in the synthesis of various complex organic molecules.
Used in Linear SPPS Synthesis of Ubiquitin Derivatives:
In the field of peptide synthesis, 9-BBN is used in the linear solid-phase peptide synthesis (SPPS) of ubiquitin derivatives, which are important for studying the functions and interactions of ubiquitin in cellular processes.
Used in Preparation of (Phosphonoacetyl)ornithine:
9-Borabicyclo[3.3.1]nonane is used in the preparation of (phosphonoacetyl)ornithine, a compound used to study the effects on arginine biosynthetic genes in yeast, providing insights into the regulation of arginine metabolism.
Purification Methods
It is available as the solid dimer or in tetrahydrofuran solution. The solid is relatively stable and can be purified by distillation in a vacuum (as dimer) and by recrystallisation from tetrahydrofuran (solubility at room temperature is 9.5%, 0.78M), filter off the solid under N2, wash it with dry pentane and dry it in vacuo at ca 100o. The solid is a dimer (IR 1567cm-1), stable in air (for ca 2 months), and can be heated for 24hours at 200o in an inert atmosphere without loss of hydride activity. It is a dimer in tetrahydrofuran solution also (IR 1567cm-1). It is sensitive to H2O and air (O2) in solution. Its concentration in solution can be determined by reaction with MeOH and measuring the volume of H2 liberated, or it can be oxidised to cis-cyclooctane-1,5-diol (m 73.5-74.5o). [IR: Knights & Brown J Am Chem Soc 90 5280 1968, Brown et al. J Am Chem Soc 96 7765 1974, Brown et al. J Org Chem 41 1778 1976, Brown & Chen J Org Chem 46 3978 1981, Fieser & Fieser Reagents for Org Synth 2 31, 3 24, 10 48, 15 43, 17, 49.] Borane pyridine complex [110 -51 -0] M 92.9, m 8-10o, 10-11o, b 86o/7mm, 100-1 0 1o/12mm, d 4 0.785. Dissolve it in Et2O and wash it with H2O in which it is insoluble. Evaporate the Et2O and distil the residual oil to gives better than 99.8% purity. Its vapour pressure is less than 0.1mm at room temperature. [Taylor et al. J Am Chem Soc 77 1506 1955, Beilstein 20 IV 2235.]
Check Digit Verification of cas no
The CAS Registry Mumber 280-64-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,8 and 0 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 280-64:
(5*2)+(4*8)+(3*0)+(2*6)+(1*4)=58
58 % 10 = 8
So 280-64-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H14B/c1-3-7-5-2-6-8(4-1)9-7/h7-8H,1-6H2
280-64-8Relevant articles and documents
A novel diaminoborate ligand system derived from 1,8-diaminonaphthalene and 9-BBN: Preparation of titanium and zirconium complexes and crystal structure of the titanium complex
Bar-Haim, Galia,Shach, Romem,Kol, Moshe
, p. 229 - 230 (1997)
1,8-Diaminonaphthalene reacts selectively with 1 equiv. of 9-BBN to form a bridging amine-aminoborane, and with 2 equiv. of 9-BBN to form a non-bridging bis(aminoborane); these aminoboranes give rise to a novel diaminoborate (4e,1-) ligand system by reactions with dimethylamides of titanium and zirconium.
Interactions of C?F Bonds with Hydridoboranes: Reduction, Borylation and Friedel–Crafts Alkylation
Bamford, Karlee L.,Chitnis, Saurabh S.,Qu, Zheng-wang,Stephan, Douglas W.
supporting information, p. 16014 - 16018 (2018/10/15)
The stoichiometric reactions of the alkylfluorides 1-fluoroadamantane (Ad-F), fluorocyclohexane (Cy-F), 1-fluoropentane (Pent-F) and benzyl fluorides with secondary boranes pinacolborane (HBpin), catecholborane (HBcat), 9-borabicyclo(3.3.1)nonane (9-BBN)
SALTS OF 2-FLUORO-N-METHYL-4-[7-(QUINOLIN-6-YL-METHYL)-IMIDAZO[1,2-b][1,2,4]TRIAZIN-2-YL]BENZAMIDE AND PROCESSES RELATED TO PREPARING THE SAME
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Page/Page column 22, (2009/12/05)
The present invention is directed to dihydrochloric acid and dibenzenesulfonic acid salts of the c-Met kinase inhibitor 2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)-imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide, and pharmaceutical compositions thereof, useful in the treatment of cancer and other diseases related to the dysregulation of kinase pathways. The present invention further relates to processes and intermediates for preparing 2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide, and salts thereof.
A New Efficient Synthesis of (R,R)-2,2'-Bipyrrolidine: An Interesting Chiral 1,2-Diamine with C2 Symmetry
Alexakis, Alexandre,Tomassini, Axel,Chouillet, Cyril,Roland, Sylvain,Mangeney, Pierre,Bernardinelli, Gerald
, p. 4093 - 4095 (2007/10/03)
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