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HomeProduct name listDIBUTYLBORON TRIFLUOROMETHANESULFONATE

DIBUTYLBORON TRIFLUOROMETHANESULFONATE

Synonym(s):Dibutylboron triflate solution

DIBUTYLBORON TRIFLUOROMETHANESULFONATE Structural

What is DIBUTYLBORON TRIFLUOROMETHANESULFONATE?

Chemical properties

clear light yellow to orange solution

The Uses of DIBUTYLBORON TRIFLUOROMETHANESULFONATE

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 1550cm1 , 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

Properties of DIBUTYLBORON TRIFLUOROMETHANESULFONATE

Boiling point: 37℃ (0.12 Torr)
Density  1.271 g/mL at 25 °C
Flash point: 80 °F
storage temp.  2-8°C
form  Solution
color  Clear light yellow to orange
BRN  1968660

Safety information for DIBUTYLBORON TRIFLUOROMETHANESULFONATE

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H226:Flammable liquids
H314:Skin corrosion/irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H336:Specific target organ toxicity,single exposure; Narcotic effects
H351:Carcinogenicity
H373:Specific target organ toxicity, repeated exposure
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P310:Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for DIBUTYLBORON TRIFLUOROMETHANESULFONATE

InChIKey FAVAVMFXAKZTMV-UHFFFAOYSA-N

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