Dicyclohexyl(trifluoromethanesulfonyloxy)borane

Base Information

• Chemical Name: Dicyclohexyl(trifluoromethanesulfonyloxy)borane
• CAS No.: 145412-54-0
• Molecular Formula: C13H22 B F3 O3 S
• Molecular Weight: 326.188
• Hs Code.: 2931900090
• European Community (EC) Number: 623-963-4
• DSSTox Substance ID: DTXSID00449839
• Nikkaji Number: J519.579I
• Wikidata: Q82269368
• Mol file: 145412-54-0.mol

Synonyms:Dicyclohexyl(trifluoromethanesulfonyloxy)borane;145412-54-0;dicyclohexylboranyl trifluoromethanesulfonate;Dicyclohexylboron Triflate;Dicyclohexylboron trifluoromethanesulfonate;Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dicyclohexylborinic acid;SCHEMBL1652769;DTXSID00449839;FBVDLYBQGQLANQ-UHFFFAOYSA-N;MFCD06797094;AKOS015840733;AS-80311;D2943;T70292;Dicyclohexylboron trifluoromethanesulfonate, 97%;Dicyclohexyl[[(trifluoromethyl)sulfonyl]oxy]borane;J-008099;Trifluoromethanesulfonic Acid Dicyclohexylboryl Ester

Chemical Property of Dicyclohexyl(trifluoromethanesulfonyloxy)borane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 59-65°C
• Refractive Index: 1.449
• Boiling Point: 337.874°C at 760 mmHg
• Flash Point: 158.141°C
• PSA: 51.75000
• Density: 1.207g/cm³
• LogP: 5.59350
• Storage Temp.: Refrigerator
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 326.1334804
• Heavy Atom Count: 21
• Complexity: 403

Purity/Quality:

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

Dicyclohexyl(trifluoromethanesulfonyloxy)borane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R34:
• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 36/37/39-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1CCCCC1)(C2CCCCC2)OS(=O)(=O)C(F)(F)F

Technology Process of Dicyclohexyl(trifluoromethanesulfonyloxy)borane

There total 5 articles about Dicyclohexyl(trifluoromethanesulfonyloxy)borane 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%

trifluorormethanesulfonic acid (1493-13-6) + bis(cyclohexanyl)borane (1568-65-6) → dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane (145412-54-0)

Guidance literature:

In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.1c00008

Reference yield: 77.0%

trifluorormethanesulfonic acid (1493-13-6) + dimethylsulfide borane complex (13292-87-0) + cyclohexene (110-83-8) → dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane (145412-54-0)

Guidance literature:

dimethylsulfide borane complex; cyclohexene; In diethyl ether; at 0 ℃; for 3h; Inert atmosphere;

trifluorormethanesulfonic acid; In hexane; at 0 - 20 ℃; for 2h;

DOI:10.1021/acs.orglett.9b00722

Reference yield:

cyclohexene (110-83-8) → dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane (145412-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 30.0 g / borane-dimethyl sulfide complex / diethyl ether / 3.5 h / 0 °C

2: 80 percent / hexane / 20 °C

With dimethylsulfide borane complex; In diethyl ether; hexane;

DOI:10.1021/jo0257896

upstream raw materials:

trifluorormethanesulfonic acid

tricyclohexylborane

bis(cyclohexanyl)borane

cyclohexene

Downstream raw materials:

dicyclohexylboranyl-acetic acid 2,6-diisopropyl-phenyl ester

C₂₀H₂₉BO

Refernces

• 1、 Thomas, Angela Y.,Walls Iii, Tommy L.,Nelson, Brionna N.,Primeaux, Stafford W.,Chanda, Prem B.. "Temperature-and Reagent-Controlled Complementary Syn-and Anti-Selective Enolboration-Aldolization of Substituted Phenylacetates". . p. 6184 - 6194. Retrieved 2021.
• 2、 Klüppel, André,Gille, Annika,Karayel, Ceren Ester,Hiersemann, Martin. "Synthesis of a diastereomer of the marine macrolide lytophilippine A". supporting information. p. 2421 - 2425. Retrieved 2019/03/29.