Dibutylboranyl trifluoromethanesulfonate

Base Information

• Chemical Name: Dibutylboranyl trifluoromethanesulfonate
• CAS No.: 60669-69-4
• Molecular Formula: C9H18BF3O3S
• Molecular Weight: 274.112
• Hs Code.: 29310099
• DSSTox Substance ID: DTXSID20369121
• Nikkaji Number: J274.160A
• Wikipedia: Dibutylboron_trifluoromethanesulfonate
• Mol file: 60669-69-4.mol

Synonyms:60669-69-4;dibutylboranyl trifluoromethanesulfonate;Dibutylboron trifluoromethanesulfonate;DIBUTYLBORYL TRIFLUOROMETHANESULFONATE;Dibutylboron triflate;Dibutyl(((trifluoromethyl)sulfonyl)oxy)borane;Dibutylboryl triflate;nBu2BOTf;Bu2BOTf;(n-Bu)2BOTf;C9H18BF3O3S;SCHEMBL408053;DTXSID20369121;BCP24700;BP-20540A;AKOS015915614;(Trifluoromethylsulfonyloxy)dibutylborane;dibutyl(trifluoromethylsulfonyloxy)borane;AS-49342;BP-20540;FT-0640706;J-520242;(Dibutylboryl trifluoromethanesulfonate)

Chemical Property of Dibutylboranyl trifluoromethanesulfonate

Chemical Property:

• Vapor Pressure: 0.0364mmHg at 25°C
• Refractive Index: 1.394
• Boiling Point: 37℃ (0.12 Torr)
• Flash Point: 80 °F
• PSA: 51.75000
• Density: 1.271 g/mL at 25 °C
• LogP: 4.52510
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 274.1021803
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

97% ^*data from raw suppliers

Dibutylboryl trifluoromethanesulfonate solution ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C,F+,F
• Statements: 12-22-34-66-67-40-10-37-65-48/20-11-63-19
• Safety Statements: 9-16-26-33-36/37/39-45-62

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(CCCC)(CCCC)OS(=O)(=O)C(F)(F)F
• Uses: Dibutylboryl trifluoromethanesulfonate may be used in the following studies:Stereo- and regio-selective synthesis of erythro aldols. As a promoter for the solution and polymer-supported trichloroacetimidate-based glycosylations.Synthesis of β-alkoxy carbonyl compounds via one-step Mukaiyama aldol-type reaction.Aldol-type cyclization for the stereoselective synthesis of cyclic ethers.As a reagent for the formation of boron enolates. As a complexation aid for the isolation of 1-acyldipyrromethanes.As a promoter in [1,2]-Wittig reaction between aldehydes and O-benzyl or O-allyl glycolate esters, creating two contiguous stereocenters (1,2-diol) in good yield without the need for strong base.

Technology Process of Dibutylboranyl trifluoromethanesulfonate

There total 1 articles about Dibutylboranyl trifluoromethanesulfonate 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: 84.0%

tributyl borane (122-56-5) + trifluorormethanesulfonic acid (1493-13-6) → di-n-butylboryl trifluoromethanesulfonate (60669-69-4)

Guidance literature:

trifluoromethanesulfonic acid addn. to tributylborane under Ar, stirring for 3 h, all at 25°C in the presence of oxygen or air; vac. distn. under Ar, IR anal.;

DOI:10.1246/bcsj.53.174

Reference yield: 93.0%

5-methyl-2-phenylpyridine (27012-22-2) + di-n-butylboryl trifluoromethanesulfonate (60669-69-4) → C20H28BN

Guidance literature:

With triethylamine; In dichloromethane; toluene; at 80 ℃; for 10h; Inert atmosphere; Sealed tube; Schlenk technique;

DOI:10.1016/j.tetlet.2020.152199

Reference yield: 93.0%

di-n-butylboryl trifluoromethanesulfonate (60669-69-4) + 1-(p-methylbenzoyl)-5-phenyldipyrromethane (171523-03-8) → 10-(dibutylboryl)-1-(4-methylbenzoyl)-5-phenyldipyrromethane (750646-90-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.5 - 1h;

upstream raw materials:

tributyl borane

trifluorormethanesulfonic acid

Downstream raw materials:

di-n-butylboron enolate of (S)-4-benzyl-N-propionyl-2-oxazolidinone

C₁₇H₃₂BNO₃

(4S,5S)-2-[1-Chloro-meth-(Z)-ylidene]-3-dibutylboranyl-4-methoxymethyl-5-phenyl-oxazolidine

Refernces

Total synthesis of the latrunculins

10.1021/ja00034a036

The research details the total synthesis of latrunculins A and B, two architecturally novel toxins isolated from the Red Sea sponge Latrunculia magnifica. The study presents highly convergent and stereocontrolled routes to achieve these syntheses, with the longest linear sequences being 16 and 12 steps, respectively. Key chemicals and strategies involved in the synthesis include the aldol reaction of aldehyde (-)-12 with methyl ketone (-)-13, an acid-catalyzed reorganization-equilibration of ortho ester (-)-11, and a Mitsunobu macrolide cyclization. The synthesis also involves the preparation of various intermediates such as aldehyde (-)-12 derived from (f)-2-allylcyclopentanone and (+)-(R,R)-2,3-butanediol, and ketone (-)-13 derived from L-cysteine ethyl ester. The research highlights the challenges and solutions in achieving the correct stereochemistry and configuration of the target compounds, showcasing the importance of protecting group strategies and selective reagents like lithium bis(trimethylsilyl)amide and dibutylboron triflate. The successful synthesis of latrunculins A and B provides valuable insights into the structure and function of these toxins, which have significant biological profiles and potential applications in studying actin microfilament structure and function.