86872

Tetrabutylammonium fluoride trihydrate

≥97.0% (NT)

• Sinonimo/i: TBAF
• Formula condensata: [CH₃(CH₂)₃]₄NF · 3H₂O
• Numero CAS: 87749-50-6
• Peso molecolare: 315.51
• Beilstein: 3761900
• Numero CE: 207-057-2
• Numero MDL: MFCD00149981
• Codice UNSPSC: 12352107
• ID PubChem: 57653206
• NACRES: NA.22

Proprietà

• Livello qualitativo: 200
• Saggio: ≥97.0% (NT)
• Stato: crystals
• Punto di fusione: 62-63 °C (lit.)
• Gruppo funzionale: amine
• Stringa SMILE: O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC
• InChI: 1S/C16H36N.FH.3H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;;;/h5-16H2,1-4H3;1H;3*1H2/q+1;;;;/p-1; VEPTXBCIDSFGBF-UHFFFAOYSA-M

Descrizione

Descrizione generale

Tetrabutylammonium fluoride trihydrate is a mild base used in reactions like aldol-type condensation reactions, Michael-type reactions, ring-opening reactions. Its is also used as a promoter in cross-coupling reactions and cyclization of carbocycles and heterocycles.[1]

Applicazioni

Reactant for:
Preparation of deprotecting agents in preparation of cellulose derivatives
Synthesis of lipophilic peptides for DNA transfections in vivo
Dehydrobromination reactions

Tetrabutylammonium fluoride trihydrate can be used as a base:

• For the dehydrobromination of vinyl bromides to terminal acetylenes.[1]
• In the conversion of 1,1-dibromo-1-alkenes to terminal alkynes via Corey–Fuchs reaction.[2]
• In Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryltrialkoxysilanes in the presence of a palladium catalyst.[3]

It can be used to catalyze ethynylation of quinolines and isoquinolines using calcium carbide in aqueous N,N-dimethylacetamide.[4]

Altre note

Reagent for the cleavage of silyl ethers and other silyl protecting groups[5]; Catalyst for various reactions with silicon compounds[6][7]; Use as a base in organic synthesis[8]; Instability of anhydrous TBAF [9]

Informazioni sulla sicurezza

• Pittogrammi: GHS08,GHS07
• Avvertenze: Warning
• Indicazioni di pericolo: H302,H315,H319,H361fd,H412
• Consigli di prudenza: P202 - P273 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Classi di pericolo: Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2
• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable
• Dispositivi di protezione individuale: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges