Diisopinocampheylborane

Base Information

• Chemical Name: Diisopinocampheylborane
• CAS No.: 21947-87-5
• Molecular Formula: C20H35B
• Molecular Weight: 286.309
• Mol file: 21947-87-5.mol

Synonyms:Borane,bis(2,6,6-trimethylbicyclo[3.1.1]hept-3-yl)-, [1S-[1a,2b,3a(1R*,2S*,3R*,5R*),5a]]-;Borane, di-3-pinanyl-, (+)-(8CI);(+)-Diisopinocampheylborane;d-Diisopinocampheylborane;

Chemical Property of Diisopinocampheylborane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 351.475oC at 760 mmHg
• Flash Point: 166.367oC
• PSA: 0.00000
• LogP: 5.40410
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Dichloromethane (Slightly), THF (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Diisopinocampheylborane(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Diisopinocampheylborane is a hydroborane with many applications in organic synthesis of nicotine analogs, (-)-Invictolide, (+)-strictifolione and other organic compounds.

Technology Process of Diisopinocampheylborane

There total 7 articles about Diisopinocampheylborane 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: 99.0%

(-)-α-pinene (7785-26-4,25766-18-1) → L-diisopinocampheylborane (21947-87-5)

Guidance literature:

With borane N-ethyl-N-isopropylaniline complex; In 1,4-dioxane;

DOI:10.1016/S0040-4020(99)00272-0

Reference yield: 82.0%

(-)-α-pinene (7785-26-4,25766-18-1) + dimethylsulfide borane complex (13292-87-0) → L-diisopinocampheylborane (21947-87-5)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201501252

Reference yield:

dimethylsulfide borane complex (13292-87-0) + (1R,5R)-(+)-β-pinene (127-91-3,25719-60-2) → L-diisopinocampheylborane (21947-87-5)

Guidance literature:

In tetrahydrofuran; pinene was slowly added to THF soln. of BMS at 0°C (N2); stirring for 2.5 h; evapn.;

DOI:10.1021/ja00379a068

upstream raw materials:

(-)-α-pinene

dimethylsulfide borane complex

(1R,5R)-(+)-β-pinene

borane-THF

Downstream raw materials:

(+)-B-methoxydiisocamphenylborane

Refernces

• 1、 Brown,H.C. et al.. "-". . p. 397 - 403. Retrieved 1964.
• 2、 Abbott, Jason R.,Allais, Christophe,Roush, William R.. "Enantioselective reductive syn-aldol reactions of 4-acryloylmorpholine: Preparation of (2R, 3S)-3-hydroxy-2-methyl-1-morpholino-5-phenylpentan-1-one". . p. 38 - 57. Retrieved 2016/08/23.
• 3、 Chen, Tao,Altmann, Karl-Heinz. "Directed hydrogenations and an Ireland-Claisen rearrangement linked to Evans-Tishchenko chemistry: The highly efficient total synthesis of the marine cyclodepsipeptide doliculide". supporting information. p. 8403 - 8407. Retrieved 2015/06/02.