261475

Dibutylboryl-trifluormethansulfonat -Lösung

1.0 M in methylene chloride

• Synonym(e): Dibutylboron triflate solution
• Lineare Formel: CF₃SO₃B[(CH₂)₃CH₃]₂
• CAS-Nummer: 60669-69-4
• Molekulargewicht: 274.11
• Beilstein: 1968660
• MDL-Nummer: MFCD00009669
• UNSPSC-Code: 12352106
• PubChem Substanz-ID: 24855812
• NACRES: NA.22

Eigenschaften

• Form: liquid
• Konzentration: 1.0 M in methylene chloride
• Dichte: 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
• InChIKey: FAVAVMFXAKZTMV-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

Dibutylboryl trifluoromethanesulfonate (Dibutylboron triflate, Bu₂BOTf) is an organometallic reagent. It efficiently promotes the1,4-addition of benzylic and allylic organocopper reagents.[1]

Anwendung

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]

Sicherheitshinweise

• Piktogramme: GHS02,GHS08,GHS05,GHS07
• Signalwort: Danger
• H-Sätze: H226,H314,H336,H351
• P-Sätze: P202 - P210 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Gefahreneinstufungen: Carc. 2 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3
• Zielorgane: Central nervous system
• Lagerklassenschlüssel: 3 - Flammable liquids
• WGK: WGK 3
• Flammpunkt (°F): 80.6 °F - closed cup
• Flammpunkt (°C): 27 °C - closed cup
• Persönliche Schutzausrüstung: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter