Disiamylborane

Base Information

• Chemical Name: Disiamylborane
• CAS No.: 1069-54-1
• Molecular Formula: C10H23 B
• Molecular Weight: 154.104
• Hs Code.: 2931900090
• UNII: 2O6VD8483R
• DSSTox Substance ID: DTXSID40910174
• Wikipedia: Disiamylborane
• Wikidata: Q2402883
• Mol file: 1069-54-1.mol

Synonyms:Borine,bis(1,2-dimethylpropyl)- (6CI); Bis(1,2-dimethylpropyl)borane;Bis(3-methyl-2-butyl)borane; DSB; Disiamylborane

Chemical Property of Disiamylborane

Chemical Property:

• Vapor Pressure: 0.975mmHg at 25°C
• Melting Point: 35-40°
• Boiling Point: 185°Cat760mmHg
• Flash Point: 65.7°C
• PSA: 0.00000
• Density: g/cm³
• LogP: 3.35170
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 153.1814559
• Heavy Atom Count: 11
• Complexity: 85

Purity/Quality:

98%,99%, ^*data from raw suppliers

DISIAMYLBORANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [B](C(C)C(C)C)C(C)C(C)C
• Uses: Selective reagent for steric control of hydroboration of olefins.

Technology Process of Disiamylborane

There total 9 articles about Disiamylborane 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:

2-methyl-but-2-ene (513-35-9) → bis-(1,2-dimethylpropyl)borane (1069-54-1)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In diethylene glycol dimethyl ether;

DOI:10.1021/ja01497a062

Reference yield:

2-methyl-but-2-ene (513-35-9) + dimethylsulfide borane complex (13292-87-0) → bis-(1,2-dimethylpropyl)borane (1069-54-1)

Guidance literature:

In tetrahydrofuran; at -10 - 0 ℃; Inert atmosphere;

DOI:10.1055/s-0033-1339185

Reference yield:

borane-THF (14044-65-6) + 2-methyl-but-2-ene (513-35-9) → bis-(1,2-dimethylpropyl)borane (1069-54-1)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol4010917

upstream raw materials:

2-methyl-but-2-ene

2,3-Dimethyl-2-butene

dimethyl sulfide borane

lithium bis(3-methyl-2-butyl)borohydride

Downstream raw materials:

C₁₉H₂₈BF₃

(1E,7E)-1,8-di(cyclohex-1-en-1-yl)octa-1,7-diene-3,5-diyne

C₁₉H₃₁B

(2-cyclohex-1-enyl-vinyl)-bis-(1,2-dimethyl-propyl)-borane

Refernces

• 1、 Yadav,Reddy,Ramalingam. "Short-route synthesis of (3E,5Z)-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle". . p. 223 - 225. Retrieved 2001.
• 2、 Ross, Sean P.,Rahman, Ajara A.,Sigman, Matthew S.. "Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction". . p. 10516 - 10525. Retrieved 2020.
• 3、 Yang, Lin,Lin, Zuming,Huang, Sha-Hua,Hong, Ran. "Stereodivergent synthesis of functionalized tetrahydropyrans accelerated by mechanism-based allylboration and bioinspired oxa-michael cyclization". . p. 6280 - 6284. Retrieved 2016.
• 4、 Brown,H.C. et al.. "-". . p. 1392 - 1398. Retrieved 1977.
• 5、 Kiernicki, John J.,Zeller, Matthias,Szymczak, Nathaniel K.. "Requirements for Lewis Acid-Mediated Capture and N-N Bond Cleavage of Hydrazine at Iron". . p. 1147 - 1154. Retrieved 2019.
• 6、 Zweifel,G. et al.. "-". . p. 190 - 195. Retrieved 1962.
• 7、 Brown, Herbert C.. "Molecular addition compounds. 13. N,N-diisopropyl-n-isobutylamine-borane: The first highly reactive trialkylamine-borane reagent for hydroborations". . p. 1310 - 1317. Retrieved 1999.
• 8、 Brown,Zweifel. "-". . p. 3834,3840. Retrieved 1961.
• 9、 Suto, Takahiro,Yanagita, Yuta,Nagashima, Yoshiyuki,Takikawa, Shinsaku,Kurosu, Yasuhiro,Matsuo, Naoya,Sato, Takaaki,Chida, Noritaka. "Unified Total Synthesis of Madangamines A, C, and E". . p. 2952 - 2955. Retrieved 2017.
• 10、 Wu, Jui-Lin,Chiou, Wen-Hua. "Diastereocontrolled Formal Syntheses of (±)-Lepadiformines A, B, and C and the Divergent Synthesis of 2- epi-Lepadiformine C through Unexpected Double Consecutive Epimerizations". . p. 9051 - 9063. Retrieved 2020.