9-Methoxy-9-borabicyclo[3.3.1]nonane

Base Information

• Chemical Name: 9-Methoxy-9-borabicyclo[3.3.1]nonane
• CAS No.: 38050-71-4
• Molecular Formula: C9H17BO
• Molecular Weight: 152.044
• Hs Code.: 2909209000
• European Community (EC) Number: 253-758-1
• DSSTox Substance ID: DTXSID80191465
• Nikkaji Number: J123.913I
• Wikidata: Q72489391
• Mol file: 38050-71-4.mol

Synonyms:9-Methoxy-9-borabicyclo[3.3.1]nonane;38050-71-4;b-methoxy-9-bbn;9-Methoxy-9-borabicyclo(3.3.1)nonane;EINECS 253-758-1;9-Borabicyclo[3.3.1]nonane, 9-methoxy-;C9H17BO;SCHEMBL925547;SCHEMBL925548;DTXSID80191465;C9-H17-B-O;AMY14867;AKOS015918506;9-methoxy-9-bora-bicyclo[3.3.1]nonane;9-Methoxy-9-borabicyclo[3.3.1]nonane #;FT-0653864;A823994;J-519514

Chemical Property of 9-Methoxy-9-borabicyclo[3.3.1]nonane

Chemical Property:

• Appearance/Colour: Colourless or yellowish l transparent liquid.
• Vapor Pressure: 0.515mmHg at 25°C
• Refractive Index: 1.441
• Boiling Point: 198.127 °C at 760 mmHg
• Flash Point: 73.625 °C
• PSA: 9.23000
• Density: 0.987 g/cm³
• LogP: 2.73250
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.1372453
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

B-Methoxy-9-BBN solution 1.0 M in hexanes ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn
• Hazard Codes: F,Xn,N
• Statements: 11-20/21/22-67-65-62-51/53-48/20-38
• Safety Statements: 16-23-36/37/39-45-62-61-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B1(C2CCCC1CCC2)OC
• Uses: Pro-nucleophile and co-catalyst for indium-catalyzed allylations of methyl ethers and carbohydrate derivatives. Catalyst for preparation of linear allenes from other allenes 2 Reactant for: Stereoconvergent Suzuki cross-coupling reactions 3 B-alkyl Suzuki-Miyaura cross-coupling reactions 4 Preparation of borabicyclononanyl amino acid complexes for selective treatment of malignant melanoma 5 Asymmetric synthesis of isomerically pure allenyl boranes through insertion and borotropic rearrangement. 9-Methoxy-9-borabicyclo[3.3.1]nonane is a coupling reagent used in reactions like the synthesis of (-)-brevenal a polycyclic ether. Pro-nucleophile and co-catalyst for indium-catalyzed allylations of methyl ethers and carbohydrate derivativesCatalyst for preparation of linear allenes from other allenesReactant for:Stereoconvergent Suzuki cross-coupling reactionsB-alkyl Suzuki-Miyaura cross-coupling reactionsPreparation of borabicyclononanyl amino acid complexes for selective treatment of malignant melanomaAsymmetric synthesis of isomerically pure allenyl boranes through insertion and borotropic rearrangement

Technology Process of 9-Methoxy-9-borabicyclo[3.3.1]nonane

There total 58 articles about 9-Methoxy-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: 100.0%

carbon dioxide (124-38-9,18923-20-1) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → 9-methoxy-9-BBN (38050-71-4)

Guidance literature:

With 1,3-di-tert-butylimidazol-2-ylidene; In tetrahydrofuran; at 70 ℃; for 0.2h; under 750.075 - 2250.23 Torr; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube;

Reference yield: 95.0%

4-methoxy-3-buten-2-one (4652-27-1) + B-trans-1-nonen-1-yl-9-borabicyclo<3.3.1>nonane (93383-91-6) → trans,trans-3,5-tridecadien-2-one (93383-92-7) + 9-methoxy-9-BBN (38050-71-4)

Guidance literature:

In diethyl ether; at 25 ℃; for 24h;

DOI:10.1021/jo00199a062

Reference yield: 92.0%

carbon dioxide (124-38-9,18923-20-1) + 9-bora-bicyclo[3.3.1]nonane (280-64-8) → methanol (67-56-1) + 9-methoxy-9-BBN (38050-71-4)

Guidance literature:

With proazaphosphatrane; In tetrahydrofuran-d8; at 20 ℃; for 192h; under 750.075 Torr; Temperature; Time; Reagent/catalyst; Catalytic behavior; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1002/anie.201407357

upstream raw materials:

methanol

1,5-cis,cis-cyclooctadiene

4-methoxy-3-buten-2-one

B-trans-1-nonen-1-yl-9-borabicyclo<3.3.1>nonane

Downstream raw materials:

B-n-butyl-9-borabicyclo<3.3.1>nonane

9-tert-Butyl-9-borabicyclo<3.3.1>nonan

allyl-9-borabicyclo<3.3.1>nonane

B-benzyl-9-BBN

Refernces

• 1、 Das Neves Gomes, Christophe,Blondiaux, Enguerrand,Thuery, Pierre,Cantat, Thibault. "Metal-free reduction of CO2 with hydroboranes: Two efficient pathways at play for the reduction of CO2 to methanol". . p. 7098 - 7106. Retrieved 2014.
• 2、 Das, Arpan,Ahmed, Jasimuddin,Rajendran,Adhikari, Debashis,Mandal, Swadhin K.. "A Bottleable Imidazole-Based Radical as a Single Electron Transfer Reagent". supporting information. p. 1246 - 1252. Retrieved 2020/12/21.
• 3、 Ramos, Alberto,Anti?olo, Antonio,Carrillo-Hermosilla, Fernando,Fernández-Galán, Rafael. "Ph2PCH2CH2B(C8H14) and Its Formaldehyde Adduct as Catalysts for the Reduction of CO2with Hydroboranes". supporting information. p. 9998 - 10012. Retrieved 2020/07/24.