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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

261475-1L:4548173356198
261475-BULK:
261475-PZ:
261475-VAR:
261475-100ML:4548173126364

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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