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261475

Sigma-Aldrich

Dibutylboryl trifluoromethanesulfonate solution

1.0 M in methylene chloride

Synonym(s):

Dibutylboron triflate solution

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About This Item

Linear Formula:
CF3SO3B[(CH2)3CH3]2
CAS Number:
60669-69-4
Molecular Weight:
274.11
Beilstein:
1968660
MDL number:
MFCD00009669
UNSPSC Code:
12352106
PubChem Substance ID:
24855812
NACRES:
NA.22

form

liquid

concentration

1.0 M in methylene chloride

density

1.271 g/mL at 25 °C

SMILES string

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

InChI

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

InChI key

FAVAVMFXAKZTMV-UHFFFAOYSA-N

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General description

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

Application

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.

Signal Word

Danger

Hazard Statements

H226,H314,H336,H351

Hazard Classifications

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

Target Organs

Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

80.6 °F - closed cup

Flash Point(C)

27 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stereo-and regio-controlled aldol synthesis.
Kuwajima I, et al.
Tetrahedron Letters, 21(44), 4291-4294 (1980)
Sanjib Das et al.
Organic letters, 6(1), 123-126 (2004-01-03)
[reaction: see text] Dibutylboron triflate/diisopropylethylamine mediated aldol-type cyclization provides an expedient route for the stereoselective synthesis of cyclic ethers in a single step. The method is highly efficient for the stereoselective synthesis of 4-cis-tetrahydropyranones. The reaction is proposed to proceed
Lian-Sheng Li et al.
Organic letters, 6(1), 127-130 (2004-01-03)
one-step Mukaiyama aldol type reaction [reaction: see text] A highly efficient one-step Mukaiyama aldol-type reaction has been developed for the synthesis of beta-alkoxy carbonyl compounds starting from ketones and acetals/ketals. The reaction is mediated by a combination of Bu(2)BOTf and
Maud Reiter et al.
The Journal of organic chemistry, 70(21), 8478-8485 (2005-10-08)
A boron-mediated syn- and anti-stereoselective aldol reaction giving rise to various beta-hydroxyenones was coupled to a Pd((II))-mediated oxidative cyclization to give 2,3,6-trisubstituted syn- and anti-dihydropyranones in good yields. The Pd((II))-mediated oxidative cyclization was expanded to alpha-hydroxyenones leading to furan-3(2H)-one derivatives
Kannan Muthukumaran et al.
The Journal of organic chemistry, 69(16), 5354-5364 (2004-08-04)
1-Acyldipyrromethanes are important precursors in rational syntheses of diverse porphyrinic compounds. 1-Acyldipyrromethanes are difficult to purify, typically streaking upon chromatography and giving amorphous powders upon attempted crystallization. A solution to this problem has been achieved by reacting the 1-acyldipyrromethane with
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