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86856

Sigma-Aldrich

Tetrabutylammonium hydrogen difluoride solution

technical, ~50% in methylene chloride (T)

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Synonym(s):
TBABF, Tetrabutylammonium bifluoride, Tetrabutylammonium difluoride
Linear Formula:
(CH3CH2CH2CH2)4N(HF2)
CAS Number:
Molecular Weight:
281.47
Beilstein:
4729304
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

technical

form

liquid

concentration

~50% in methylene chloride (T)

impurities

~5% tetrabutylammonium chloride

refractive index

n20/D 1.442

storage temp.

2-8°C

SMILES string

[F-].F[H].CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.2FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;/h5-16H2,1-4H3;2*1H/q+1;;/p-1

InChI key

ZHBDKVWQJKYIFF-UHFFFAOYSA-M

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Application

  • Used as an etchant for silica films

Reactant for:
  • Nucleophilic fluorination
  • Ring-opening fluorination reaction
  • Substitution reactions
Tetrabutylammonium hydrogen difluoride (TBABF) can be used as a reagent:
  • For the conversion of aromatic boronic acids and esters into corresponding tetrabutylammonium trifluoroborate salts. These salts are utilized as surrogates of boronic acids in Suzuki-Miyaura cross-coupling reactions.
  • In the nucleophilic fluorination of organic halides, tosylates, and triflates.
  • For the regioselective synthesis of fluorohydrins by ring-opening of terminal epoxides.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tetrabutylammonium Bifluoride
Prakash GS and Pertusati F
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)

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