9-Borabicyclo[3.3.1]nonane Chemical Properties

Melting point:

140-142 °C

Boiling point:

68-70 °C

Density 

0.894 g/mL at 25 °C

Flash point:

1 °F

storage temp. 

Flammables area

solubility 

Miscible with ether, hexane, benzene, toluene, carbon tetrachloride, chloroform, dimethylsulfide and dichloromethane. Slightly miscible with cyclohexane, dimethoxyethane, diglyme and dioxane.

Water Solubility 

reacts

Sensitive 

Air & Moisture Sensitive

BRN 

605509

Exposure limits

ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)

InChIKey

FEJUGLKDZJDVFY-OCAPTIKFSA-N

EPA Substance Registry System

9-Borabicyclo[3.3.1]nonane (280-64-8)

Safety Information

Hazard Codes 

F,Xn,Xi,N

Risk 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

RIDADR 

UN 3399 4.3/PG 1

WGK Germany 

3

F 

1-10-34

HazardClass 

4.1

PackingGroup 

III

HS Code 

29319090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

9-Borabicyclo[3.3.1]nonane Usage And Synthesis

Chemical Properties

WHITE CRYSTALLINE POWDER

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.

Uses

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

General Description

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.

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.]

9-Borabicyclo[3.3.1]nonane(280-64-8)Related Product Information

• N-NONANE
• N-N-BUTYL-N-BUTAN-4-OL-NITROSAMINE
• 9-BBN TRIFLATE
• 9-BROMO-9-BORABICYCLO[3.3.1]NONANE,B-Bromo-9-borabicyclo[3.3.1]nonane,9-Bromo-9-borabicyclo[3.3.1]nonane solution
• B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE,(R)-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane,b-isopinocampheyl-9-borabicyclo[3.3.1]nonane solution
• 9-Borabicyclo[3.3.1]nonane,9-methoxy
• B-Benzyl-9-borabicyclo[3.3.1]nonane
• Bis-9-borabicyclo[3.3.1]nonane ,9-BORABICYCLO[3.3.1]NONANE DIMER,9-BORABICYCLO[3.3.1]NONANE,9-BORABICYCLO[3.3.1]NONANE,9-BORABICYCLO[3.3.1]NONANE DIMER
• Lithium 9-borabicyclo[3.3.1]nonane hydride
• B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE
• 9-(1,1,2-Trimethylpropoxy)-9-borabicyclo[3.3.1]nonane
• Boron
• Cyclooctane
• LITHIUM B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE
• 9-BBN-NOPOL BENZYL ETHER ADDUCT
• 9-iodo-9-borabicyclo[3.3.1]nonane solution,9-IODO-9-BORABICYCLO[3.3.1]NONANE
• LITHIUM B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE
• LITHIUM HYDRIDO(9-BBN-NOPOL BENZYL ETHER ADDUCT)