216143

Tetrabutylammonium fluoride solution

1.0 M in THF

• Synonym(s): TBAF solution
• Linear Formula: [CH₃(CH₂)₃]₄NF
• CAS Number: 429-41-4
• Molecular Weight: 261.46
• Beilstein/REAXYS Number: 3762762
• MDL number: MFCD00011747
• UNSPSC Code: 12352116
• PubChem Substance ID: 24852802
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 200
• concentration: 1.0 M in THF
• impurities: ~5 wt. % water
• density: 0.903 g/mL at 25 °C
• storage temp.: 2-8°C
• SMILES string: [F-].CCCC[N+](CCCC)(CCCC)CCCC
• InChI: 1S/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
• InChI key: FPGGTKZVZWFYPV-UHFFFAOYSA-M

Description

Application

Reactant for preparation of:

• Triple monoamine reuptake inhibitors as a new generation of antidepressants
• Alcohols via hydrolysis of alkyl silyl ethers neutral pH in mixed organic-aqueous buffered solutions
• Oligoribonucleotides with phosphonate-modified linkages
• Aryl alkyl alcohols via Nozaki-Hiyama allylation catalyzed by chiral bipyridyldiol ligands and chromium trichloride
• Conjugated dienoic acid esters using Suzuki coupling reactions
• Macrocyclic o-aminobenzamide Hsp90 inhibitorwith antitumor activity
• Phospshoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors
• Anti-diabetic polyacetylenic glucosides

Tetrabutylammonium fluoride (TBAF) can be used as a reagent:

• For the deprotection of silyl and N-sulfonyl groups.
• In the fluorination reactions.
• To synthesize 2-substituted indoles by cyclization reaction of various 2-ethynylanilines with terminal alkynes using Pd catalyst. It can also be used as an activator in the synthesis of arylated or alkenylated alkynes by the coupling reaction of aryl and alkenyl halides with terminal alkynes in the presence of Pd catalyst.

Safety Information

• pictograms: GHS02,GHS08,GHS07
• signalword: Danger
• hcodes: H225,H302,H315,H319,H335,H336,H351,H361fd,H412
• pcodes: P210 - P273 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Central nervous system, Respiratory system
• supp_hazards: EUH019,EUH032
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 1.4 °F - closed cup
• flash_point_c: -17 °C - closed cup