ChemicalBook > CAS DataBase List > 9-Borabicyclo[3.3.1]nonane

9-Borabicyclo[3.3.1]nonane

Product Name
9-Borabicyclo[3.3.1]nonane
CAS No.
280-64-8
Chemical Name
9-Borabicyclo[3.3.1]nonane
Synonyms
9-BBN;9-BBN, 0.4M SOLUTION IN HEXANES;Kseal;9-BorabicycL;9-BBN monomer;o[3.3.1]nonane;9-BBN(0.5M in toluene);9-Borabicyclo[3.3.1]nona;9-Borabicyclo[3.3.1]none;9-BBN MonoMer, 0.5M in THF
CBNumber
CB3416592
Molecular Formula
C8H15B
Formula Weight
122.02
MOL File
280-64-8.mol
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
151076
Product name
9-Borabicyclo[3.3.1]nonane solution
Purity
0.5?M in THF
Packaging
18L
Price
$2184
Updated
2024/03/01
Sigma-Aldrich
Product number
151076
Product name
9-Borabicyclo[3.3.1]nonane solution
Purity
0.5 M in THF
Packaging
8l
Price
$2230
Updated
2024/03/01
Alfa Aesar
Product number
H52287
Product name
9-BBN monomer, 97%, 0.5M in THF
Packaging
100ml
Price
$47.6
Updated
2021/12/16
Alfa Aesar
Product number
H52287
Product name
9-BBN monomer, 97%, 0.5M in THF
Packaging
500ml
Price
$180
Updated
2021/12/16
Sigma-Aldrich
Product number
151076
Product name
9-Borabicyclo[3.3.1]nonane solution
Purity
0.5 M in THF
Packaging
4x25ml
Price
$86.3
Updated
2024/03/01
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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.]

9-Borabicyclo[3.3.1]nonane Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 9-Borabicyclo[3.3.1]nonane manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
9-Borabicyclo[3.3.1]nonane 280-64-8
Price
US $10.00/KG
Min. Order
100KG
Purity
99%
Supply Ability
100 mt
Release date
2021-09-26
Hebei Mojin Biotechnology Co., Ltd
Product
9-Borabicyclo[3.3.1]nonane 280-64-8
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-06-26
Henan Aochuang Chemical Co.,Ltd.
Product
9-Borabicyclo[3.3.1]nonane 280-64-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-26

280-64-8, 9-Borabicyclo[3.3.1]nonaneRelated Search:

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)

  • 9-Borabicyclo[3.3.1]nonane, 0.5 M solution in THF, J&KSeal
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  • 9-Borabicyclo[3.3.1]nonane Solution (9-BBN), 0.5 M in THF
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  • 9-Borabicyclo[3.3.1]nonane, 0.5M solution in THF, AcroSeal
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  • 9-Borabicyclo[3.3.1]nonane, 0.5M solution in THF, AcroSeal 100ML
  • 9-Borabicyclo[3.3.1]nonane, 0.5M solution in THF, AcroSeal 800ML
  • (9-BBN)9-Borabicyclo[3.3.1]nonane,0.5M solution inTHF
  • 9-BBN MonoMer, 97%, 0.5M in THF
  • 9-Borabicyclo[3.3.1]nonane, 0.5 M solution in THF, SpcSeal
  • 9-Borabicyclo[3.3.1]Nonane,0.5M In THF
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  • Kseal
  • 0.5mol/L 9-Borabicyclo[3.3.1]nonane, Tetrahydrofuran Solution
  • 9-Borabicyclo[3.3.1]nonane, for synthesis, 0.5 M solution in THF, J&amp
  • 9λsup2sup-borabicyclo[3.3.1]nonane
  • 9-Borabicyclo[3.3.1]nonane (1M solution in THF)
  • 9- Borobicyclo [3.3.1] nonane
  • 9-Borabicyclo[3.3.1]nonane (8CI, 9CI, ACI)
  • 9-Borabicyclo(3,3,1)nonane .5 M in THF
  • 9-borobicyclo (3,3,1)none 0.5M in THF
  • 280-64-8
  • C8H14B
  • C8H15B
  • Reduction
  • Synthetic Reagents
  • Boranes