dibutylboranyl trifluoromethanesulfonate

• ChemBase ID: 137476
• Molecular Formular: C9H18BF3O3S
• Molecular Mass: 274.1086296
• Monoisotopic Mass: 274.1021805
• SMILES: B(CCCC)(CCCC)OS(=O)(=O)C(F)(F)F
• Canonical SMILES: CCCCB(OS(=O)(=O)C(F)(F)F)CCCC
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: dibutylboranyl trifluoromethanesulfonate
• IUPAC Traditional name: dibutylboranyl trifluoromethanesulfonate
• Synonyms: Dibutylboron triflate solution; Dibutylboryl trifluoromethanesulfonate solution; Dibutylboryl trifluoromethanesulfonate solution; Dibutylboron triflate solution; 二丁基硼三氟甲磺酸盐 溶液; 三氟甲磺酸二丁硼 溶液; 三氟甲磺酸二丁硼 溶液; 二丁基硼三氟甲磺酸盐 溶液

Database IDs

• CAS Number: 60669-69-4
• MDL Number: MFCD00009669
• Beilstein Number: 1968660
• PubChem SID: 24861390; 162231738; 24855812; 24853816
• PubChem CID: 2724243

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.4052
• LogD (pH = 7.4): 5.4052
• Log P: 5.4052
• Molar Refractivity: 54.7113 cm^3
• Polarizability: 23.57677 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: -16 °C; 27 °C; 3.2 °F; -40 °C; -40 °F; 80.6 °F
• Density: 0.815 g/mL at 25 °C; 0.914 g/mL at 25 °C; 1.271 g/mL at 25 °C

Safety Information

• European Hazard Symbols: Corrosive (C); Flammable (F); Highly flammable (F+)
• UN Number: 2920; 2924
• German water hazard class: 3
• Hazard Class: 3; 8
• Packing Group: 1; 2
• Risk Statements: 10-34-40; 12-22-34-66-67; 63-11-34-48/20-65-67
• Safety Statements: 16-26-36/37/39-45-62; 26-36/37/39-45; 9-16-26-33-36/37/39-45
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H314-H336-H361d-H373; H226-H314-H351
• GHS Precautionary statements: P210-P261-P280-P301 + P310-P305 + P351 + P338-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2; UN 2924 3/PG 1
• Storage Temperature: 2-8°C

Product Information

• Concentration: ~1 M in methylene chloride; 1 M in toluene; 1.0 M in diethyl ether; 1.0 M in methylene chloride
• Grade: purum
• Linear Formula: CF3SO3B[(CH2)3CH3]2

DETAILS

Sigma Aldrich - 733474

Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - 261475

Application
Promotes a [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.1
Reagent for the formation of boron enolates and as a complexation aid for the isolation of 1-acyldipyrromethanes
Packaging
100 mL in Sure/Seal™

Sigma Aldrich - 34630

Other Notes
Reagent used for the preparation of (Z)-boron enolates from ketones which react in high stereoselectivity with aldehydes to the syn aldol1,2,3,4