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216143

Tetrabutylammonium fluoride solution

1.0 M in THF

Synonym(s):

TBAF solution

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About This Item

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

liquid

Quality Segment

200

reaction suitability

core: ammonium

concentration

1.0 M in THF

impurities

~5 wt. % water

density

0.903 g/mL at 25 °C

functional group

amine

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

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.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Dam. 1 - 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

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

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