60669-69-4

Basic information

• Product Name: DIBUTYLBORON TRIFLUOROMETHANESULFONATE
• Synonyms: Dibutylboron trifluoromethanesulfonate, 1M solution in diethylether;dibutylboron triflate solution;TRIFLUOROMETHANESULFONIC ACID ANHYDRIDE WITH DIBUTYLBORINIC ACID);dibutylboryl triflate;Dibutylboron trifluoromethanesulfonate,98%;Dibutylboryl trifluoromethanesulfonate solution,Dibutylboron triflate solution;Dibutylboron trifluoroMethanesulfonate, 1M solution in diethyl ether, AcroSeal;dibutyl(((trifluoroMethyl)sulfonyl)oxy)borane
• CAS NO: 60669-69-4
• Molecular Formula: C₉H₁₈BF₃O₃S
• Molecular Weight: 274.11
• Mol File: 60669-69-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 37℃ (0.12 Torr)
• Flash Point: 80 °F
• Appearance: Clear light yellow to orange/Solution
• Density: 1.271 g/mL at 25 °C
• Vapor Pressure: 0.0364mmHg at 25°C
• Refractive Index: 1.394
• Storage Temp.: 2-8°C
• BRN: 1968660
• CAS DataBase Reference: DIBUTYLBORON TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBUTYLBORON TRIFLUOROMETHANESULFONATE(60669-69-4)
• EPA Substance Registry System: DIBUTYLBORON TRIFLUOROMETHANESULFONATE(60669-69-4)

Safety Data

• 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
• RIDADR: UN 2924 3/PG 1
• WGK Germany: 3
• F: 1-10
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 60669-69-4(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow to orange solution

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.

General Description

Dibutylboryl trifluoromethanesulfonate (Dibutylboron triflate, Bu2BOTf) is an organometallic reagent. It efficiently promotes the1,4-addition of benzylic and allylic organocopper reagents.

Purification Methods

Distil it in a vacuum under argon and store it under argon. It should be used within 2 weeks of purchase or after redistillation. Use a short path distillation system. It has IR bands in CCl4 at max 1405, 1380, 1320, 1200 and 1550cm
1 , and 1 3C NMR (CDCl3) with at 118.1, 25.1, 21.5 and 13.6ppm. [Gage & Evans Org Synth 68 83 1990, Evans et al. J Am Chem Soc 103, 3099 1981.] TOXIC

InChI:InChI=1/C9H18BF3O3S/c1-3-5-7-10(8-6-4-2)16-17(14,15)9(11,12)13/h3-8H2,1-2H3

Upstream product

• 122-56-5 tributyl borane 
• 1493-13-6 trifluorormethanesulfonic acid 

Downstream Products

• 131698-89-0 Pinacolone dibutylborone enolate 

Relevant articles and documents

Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes

Cross-electrophile coupling reactions of two Csp3-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.

Temperature-controlled regioselectivity in the reductive cleavage of p-methoxybenzylidene acetals

The regioselective ring opening of pyranosidic 4,6-p-methoxybenzylidene acetals with BH3/Bu2BOTf in THF can be tuned by adjusting the reaction temperature and reagent concentrations. Reductive cleavage at 0 °C resulted in the exclusive formation of 4-O-p-methoxybenzyl (PMB) ethers, whereas reaction at -78 °C produced 6-O-PMB ethers in high yields. The latter condition was observed to be compatible with a variety of acid-sensitive functional groups, including allyl and enol ethers. The presence of water does not interfere with reductive ring opening and may contribute toward in situ generation of H+ as a catalyst for 6-O-PMB ether formation. Reductive cleavage under rigorously aprotic conditions is greatly decelerated, and yields only the 4-O-PMB ether. The temperature-dependent reductive cleavage of the 4,6-acetal can be described in terms of kinetic versus thermodynamic control: Lewis-acid coordination of the more accessible O-6 is favored at higher temperatures, whereas protonation of the more basic but sterically encumbered O-4 predominates at low temperatures.