9-Borabicyclo[3.3.1]nonane

Base Information

• Chemical Name: 9-Borabicyclo[3.3.1]nonane
• CAS No.: 280-64-8
• Molecular Formula: C8H15B
• Molecular Weight: 122.018
• Hs Code.: 29319090
• European Community (EC) Number: 206-000-9
• UNII: 4K4J8L1OG9
• DSSTox Substance ID: DTXSID3074781
• Wikipedia: 9-Borabicyclo(3.3.1)nonane
• Wikidata: Q275023
• Mol file: 280-64-8.mol

Synonyms:9-BBN compound;9-borabicyclo(3,3,1)nonane

Chemical Property of 9-Borabicyclo[3.3.1]nonane

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 150 - 152oC
• Boiling Point: 179.3 °C at 760 mmHg
• Flash Point: 62.3 °C
• PSA: 0.00000
• Density: 0.894 g/mL at 25 °C
• LogP: 2.36770
• Storage Temp.: Flammables area
• Sensitive.: Air & Moisture Sensitive
• Solubility.: Miscible with ether, hexane, benzene, toluene, carbon tetrachlor
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 121.1188556
• Heavy Atom Count: 9
• Complexity: 80.7

Purity/Quality:

99% ^*data from raw suppliers

9-Borabicyclononane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn, Xi, N
• Hazard Codes: F,Xn,Xi,N
• Statements: 14-20/21/22-36/37/38-36/37-19-14/15-11-67-65-62-51/53-48/20-38-40
• Safety Statements: 16-26-36/37/39-45-43-33-62-61-36/37-29-7/8-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: [B]1C2CCCC1CCC2
• Uses: 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. Protecting group for alkenes?Reactant for: Linear SPPS synthesis of ubiquitin derivativesCopper-catalyzed cross-coupling reactions of organoboron compounds with primary alkyl halides and pseudohalidesIntramolecular insertion of alkenes into palladium-nitrogen bondsPreparation of (phosphonoacetyl)ornithine to study effect on arginine biosynthetic genes in yeastHetero-Diels-Alder reaction for synthesis of spirocyclic alkaloids

Technology Process of 9-Borabicyclo[3.3.1]nonane

There total 23 articles about 9-Borabicyclo[3.3.1]nonane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Guidance literature:

With borane N-ethyl-N-isopropylaniline complex; In 1,4-dioxane; Heating;

DOI:10.1016/S0040-4020(99)00272-0

Reference yield: 75.0%

borane-THF (14044-65-6) + 9-(di-tert-butylphosphanyl)-9-bora{3.3.1}bicyclononane (149468-33-7) → μ-(di-tert-butylphosphanyl)-diborane (149075-30-9) + 1,1,3,3-tetra-tert-butyl-1,3,2,4-diphosphadiboracyclobutane (149075-28-5) + μ-(di-tert-butylphosphanyl)-di-9-bora{3.3.1}bicyclononane (149075-29-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Guidance literature:

In tetrahydrofuran; dropping soln. of BH3*THF in THF to soln. of borane in THF at -78°C, under N2 or Ar; refluxing for 1 h; mechansim discussed;; removal of solvent in vac.; recrystn. from ether; 1. and 2. fraction product mixts., 3. fraction pure 9-borabicyclo(3.3.1)nonane, 4. fraction small amt. of pure (BH2P(tert-butyl)2)2; detn. by NMR;;

Reference yield: 70.0%

((CH3)2CH)2NCH2CH(CH3)2*BH3 + cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Guidance literature:

In 1,4-dioxane; N2-atmosphere; dropwise cyclooctadiene addn. (20°C, stirring), stirring (room temp, 3 h, refluxing , 2 h); crystn. (room temp.), decanting, washing (n-pentane), drying (reduced pressure), recrystn. (THF);

DOI:10.1021/om980629z

upstream raw materials:

1,5-cis,cis-cyclooctadiene

9-chloro-9-borabicyclo{3.3.1}nonane

cyclo-octa-1,5-diene

9-borabicyclo[3.3.1]nonane dimer

Downstream raw materials:

9-phenyl-9-borabicyclo[3.3.1]nonane

B-p-tolyl-9-borabicyclo[3.3.1]nonane

B-mesityl-9-borabicyclo[3.3.1]nonane

9-borabicyclo[3.3.1]nonane * pyridine

Refernces

1- and 2-(Trialkylsilyl)ethanols: New Silyl Reagents from Tin, Lithium, and Boron Chemistry

10.1021/jo00278a014

The research focuses on the efficient preparation of isomerically pure 1- and 2-(trialkylsilyl)ethanols using vinylsilanes with borane reagents. The study aims to address environmental drawbacks of previous methods and the limitations due to a lack of available chloromethylsilane precursors. The researchers successfully synthesized these compounds with good yields using a series of reactions involving organometallic reagents such as tin, lithium, and boron chemistry. Key chemicals used in the process include vinylsilanes, borane reagents like 9-borabicyclo[3.3.1]nonane (9-BBN), acetylsilanes, and organocyanocopper-trifluoroborane reagents. The conclusions of the study highlight the high degree of asymmetric induction, regiochemistry, and chemoselectivity achieved in the formation of chiral quaternary carbon centers with high optical purity, demonstrating the versatility and efficiency of the developed synthetic methods.

New ring expansion of cyclobutanones: Synthesis of pyrrolinones, pyrrolidines and pyrroles

10.1055/s-2004-822900

The research explores a novel method for expanding the ring structure of cyclobutanones to synthesize various five-membered azaheterocyclic compounds, including pyrrolinones, pyrrolidines, and pyrroles. The study aims to develop an efficient and high-yielding synthetic pathway for these heterocycles, which are known for their significant physiological and pharmacological properties. The researchers used 2,2-dichlorocyclobutanones as starting materials, reacting them with amines to induce ring opening, forming 4,4-dichlorobutanamides. These intermediates were then converted into enol ethers using sodium methoxide, which were subsequently cyclized to form 3-pyrrolin-2-ones by treatment with aqueous HCl. The synthesized pyrrolinones were further reduced to pyrrolidinones and pyrrolidines using hydrogen on palladium and LiAlH4, respectively. Additionally, the pyrrolinones were converted to pyrroles using 9-borabicyclo[3.3.1]nonane (9-BBN). The study concludes that this new ring expansion method provides an efficient and versatile route for synthesizing a variety of physiologically active azaheterocyclic compounds, offering good yields and scalability.

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