DIBUTYLBORON TRIFLUOROMETHANESULFONATE Property

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

InChIKey

FAVAVMFXAKZTMV-UHFFFAOYSA-N

Safety

Hazard Codes 

C,F+,F

Risk 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

HS Code 

29310099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

H335May cause respiratory irritation

H336May cause drowsiness or dizziness

H351Suspected of causing cancer

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

DIBUTYLBORON TRIFLUOROMETHANESULFONATE Chemical Properties,Usage,Production

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