900021

TBAF(pin)₂

• Synonym(s): 1-Butanaminium, N,N,N-tributyl-, fluoride, compd. with 2,3-dimethyl-2,3-butanediol (1:2:2)
• Empirical Formula (Hill Notation): C₂₈H₆₄FNO₄
• CAS Number: 1823217-44-2
• Molecular Weight: 497.81
• UNSPSC Code: 12352101
• PubChem Substance ID: 329769764

Properties

• form: powder
• mp: 162-167 °C (d)
• functional group: amine; hydroxyl
• SMILES string: OC(C)(C)C(C)(C)O.OC(C)(C)C(C)(C)O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]
• InChI: 1S/C16H36N.2C6H14O2.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;2*1-5(2,7)6(3,4)8;/h5-16H2,1-4H3;2*7-8H,1-4H3;1H/q+1;;;/p-1
• InChI key: CVEUWEZBMVLEKR-UHFFFAOYSA-M

Description

General description

TBAF(pin)₂ is a fluoride–alcohol complex with coordination number four. It can be obtained by reacting pinacol (pin) with tetrabutylammonium fluoride trihydrate (TBAF(H₂O)₃). The geometric structure and bonding of TBAF(pin)₂ have been studied.

Application

Nucleophilic fluorinating reagent is a more convenient crystalline solid for handling and storage compared to tetrabutylammonium fluoride hydrate (Aldrich 241512). As reported by Engle and Gouverneur, these solids display comparable reactivity on similar substrates.

Other Notes

Coordination diversity in hydrogen-bonded homoleptic fluoride–alcohol complexes modulates reactivity

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable