CAS 280-64-8 9-Borabicyclo(3.3.1)nonane (HCID 78966)

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Basic information

CAS: 280-64-8
Standard SMILES: B1C2CCCC1CCC2
InChIKey: FEJUGLKDZJDVFY-UHFFFAOYSA-N
Molecular formula: C8H15B
Average molar mass: 122.02 g/mol
Monoisotopic mass: 122.12668088

Overview

an amino acid protecting group

Names & identifiers

Preferred name: 9-Borabicyclo(3.3.1)nonane
IUPAC: 9-borabicyclo[3.3.1]nonane
English name: 9-Borabicyclo[3.3.1]nonane
Molecular formula: C8H15B
Molecular weight: 122.02

Names & synonyms

9-BBN compound9-BBN cpdRefChem:5492209-Borabicyclo3.3.1nonaneDTXCID2037760206-000-9280-64-84K4J8L1OG99-Borabicyclo(3,3,1)nonane9-Borabicyclo(3.3.1)nonane9-borabicyclononaneDTXSID3074781

Show more names

9-BBN9-BBN, 0.4M SOLUTION IN HEXANESKseal9-BorabicycL9-BBN monomero[3.3.1]nonane9-BBN(0.5M in toluene)9-Borabicyclo[3.3.1]nona9-Borabicyclo[3.3.1]none9-BBN MonoMer, 0.5M in THF

(1beta,5beta)-9-Borabicyclo[3.3.1]nonane

Database identifiers

CAS: 280-64-8
PubChem CID: 78966
DTXSID: DTXSID3074781
EC Number: 206-000-9

Properties

Computed structural properties

Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 0
Heavy atoms: 9
Formal charge: 0
Complexity: 80.7

Experimental & physicochemical properties

Chemical ClassesMetals -> Metalloid Compounds (Boron)

Physical DescriptionWhite solid; [Acros Organics MSDS]

Physicochemical properties

Melting point: 140 · 140-142 °C
Boiling point: 68 · 68-70 °C
Density: 0.894 g/mL · 0.894 g/mL at 25 °C
Flash point: 1 °F · 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.
form: liquid
Water Solubility: reacts
Sensitive: Air & Moisture Sensitive
BRN: 605509 · 605509
InChI: InChI=1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H250 (72.6%): Catches fire spontaneously if exposed to air [Danger Pyrophoric liquids]

P210, P222, P223, P231, P231+P232, P233, P260, P264, P280, P301+P330+P331, P302+P335+P334, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P402+P404, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 146 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 15-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/24223

9-Borabicyclo3.3.1nonane: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryReacts with water; May cause irritation; [Acros Organics MSDS]

Hazard Classes and CategoriesPyr. Sol. 1 (72.6%)

Safety data

F: 1-10-34
wgk: 3
tsca: TSCA listed
ridadr: UN 3399 4.3/PG 1
hs_code: 29319090
risk_code: 14-20/21/22-36/37/38-36/37-19-14/15-11-67-65-62-51/53-48/20-38-40
Signal word: Danger
Symbol(GHS): GHS02,GHS07,GHS08,GHS09
hazard_code: F,Xn,Xi,N
safety_code

Chemistry & industry

Uses & manufacturing

General Manufacturing Information9-Borabicyclo[3.3.1]nonane: ACTIVE

Applications · 3 items

Uses9-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.

UsesProtecting group for alkenesReactant 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

General Description9-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.