DIBUTYLBORON TRIFLUOROMETHANESULFONATE
Synonym(s):Dibutylboron triflate solution
- CAS NO.:60669-69-4
- Empirical Formula: C9H18BF3O3S
- Molecular Weight: 274.11
- MDL number: MFCD00009669
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-04-23 13:52:06
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) |
Flame Flammables GHS02 Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 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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product: Di-Butyl Boron Triflate (1.0M in Toluene) 60669-69-4
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