9-Borabicyclo[3.3.1]nonane Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H260In contact with water releases flammable gases which may ignite spontaneously

H261In contact with water releases flammable gas

H302Harmful if swallowed

H304May be fatal if swallowed and enters airways

H315Causes skin irritation

H319Causes serious eye irritation

H333May be harmful if inhaled

H335May cause respiratory irritation

H336May cause drowsiness or dizziness

H351Suspected of causing cancer

H373May cause damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P231+P232Handle under inert gas. Protect from moisture.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P331Do NOT induce vomiting.

P370+P378In case of fire: Use … for extinction.

P402+P404Store in a dry place. Store in a closed container.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

9-Borabicyclo[3.3.1]nonane Chemical Properties,Usage,Production

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.]