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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/REAXYS Number:
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.[1]

Application

Dibutylboryl trifluoromethanesulfonate may be used in the following studies:
  • Stereo- and regio-selective synthesis of erythro aldols.[2]
  • As a promoter for the solution and polymer-supported trichloroacetimidate-based glycosylations.[1]
  • Synthesis of β-alkoxy carbonyl compounds via one-step Mukaiyama aldol-type reaction.[3]
  • Aldol-type cyclization for the stereoselective synthesis of cyclic ethers.[4]
  • As a reagent for the formation of boron enolates.[5]
  • As a complexation aid for the isolation of 1-acyldipyrromethanes.[6]
  • 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.[7]

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

80.6 °F - closed cup

flash_point_c

27 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM9545
SHBK9068
SHBK3914
SHBH5053V
SHBG2618V

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Synlett, 81-81 (1992)
Dibutylboron triflate promoted conjugate addition of benzylic and allylic organocopper reagents to chiral α,β-unsaturated N-acyl imidazolidinones.
van Heerden PS, et al.
Tetrahedron Letters, 37(39), 6985-6988 (1996)
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
Myra Beaudoin Bertrand et al.
Organic letters, 8(20), 4661-4663 (2006-09-22)
A new tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters is described. This reaction generates two carbon-carbon bonds and two contiguous stereocenters in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction
Stereo-and regio-controlled aldol synthesis.
Kuwajima I, et al.
Tetrahedron Letters, 21(44), 4291-4294 (1980)
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