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261475 Sigma-Aldrich

Dibutylboryl trifluoromethanesulfonate solution

1.0 M in methylene chloride

Synonym: Dibutylboron triflate solution

  • CAS Number 60669-69-4

  • Linear Formula CF3SO3B[(CH2)3CH3]2

  • Molecular Weight 274.11

  •  Beilstein/REAXYS Number 1968660

  •  MDL number MFCD00009669

  •  PubChem Substance ID 24855812

  •  NACRES NA.22

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Properties

Related Categories Boronic Acids and Derivatives, Chemical Reagents, Chemical Synthesis, Development Quantities for Research, Organometallic Reagents,
Quality Level   100
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

Description

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.

Packaging

1 L in Sure/Seal™

100 mL in Sure/Seal™

Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
Target organs 
Central nervous system
RIDADR 
UN 2920 3(8) / PGII
WGK Germany 
WGK 3
Flash Point(F) 
80.6 °F - closed cup
Flash Point(C) 
27 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used al...
ChemFiles Volume 1 Article 3
Keywords: Acylations, Alkylations

Peer-Reviewed Papers
15

References

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