DIBUTYLBORON TRIFLUOROMETHANESULFONATE Chemical Properties

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

InChI

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

InChIKey

FAVAVMFXAKZTMV-UHFFFAOYSA-N

SMILES

B(CCCC)(CCCC)OS(=O)(=O)C(F)(F)F

Safety Information

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

Storage Class

3 - Flammable liquids

Hazard Classifications

Carc. 2
Eye Dam. 1
Flam. Liq. 3
Skin Corr. 1B
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

DIBUTYLBORON TRIFLUOROMETHANESULFONATE Usage And Synthesis

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

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