Tetrabutylammonium cyanoborohydride Chemical Properties

Melting point:

144-146 °C(lit.)

storage temp. 

water-free area

solubility 

sol most polar (e.g. alcohols, carboxylic acids), polar aprotic (e.g. HMPA, DMSO, DMF), and nonpolar (e.g. CH2Cl2, benzene, hexane) solvents; sparingly sol H2O, ether.

form 

nonhydroscopic solid

color 

white

InChI

1S/C16H36N.CH3BN/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;2-1-3/h5-16H2,1-4H3;2H3/q+1;-1

InChIKey

BOHYACMUNXBTGV-UHFFFAOYSA-N

SMILES

[BH3-]C#N.CCCC[N+](CCCC)(CCCC)CCCC

CAS DataBase Reference

43064-96-6

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36/37/38-15

Safety Statements 

26-36-7/8-37/39

WGK Germany 

3

F 

21

HS Code 

29310099

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:Tetrabutylammonium cyanoborohydride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Tetrabutylammonium cyanoborohydride Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

Tetrabutylammonium Cyanoborohydride is used in preparation method of novel biomass plastic material.

Uses

Reactant for:

• Hydroxymethylation reactions
• Radical carbonylation reactions
• Reduction reactions (reductant)

Application

Tetrabutylammonium cyanoborohydride (TBAC) is used as a selective, mild reducing reagent for aldehydes, conjugated aldehydes and ketones, alkyl iodides and bromides; useful for reductive aminations of aldehydes and ketones in nonpolar solvents.

Preparation

Tetrabutylammonium cyanoborohydride is prepared from n-Bu4NHSO4 suspended in H2O, treated with Sodium Hydroxide and Sodium Cyanoborohydride, and extracted into CH2Cl2; recrystallized from ethyl acetate. Other tetraalkylammonium derivatives are available (including polymersupported) or can be generated in situ from NaBH3CN and Aliquat 336.

reaction suitability

reagent type: reductant

Tetrabutylammonium cyanoborohydride(43064-96-6)Related Product Information

• Tetrabutylammonium perchlorate
• TETRABUTYL AMMONIUM BROMIDE
• Tetrabutylammonium phosphate
• Tetrabutyl ammonium chloride
• Tetrabutylammonium fluoride
• Tetrabutylammonium hydrogen sulfate
• Tetrabutylammonium bromide
• Tetrabutylammonium hydroxide
• Tetrabutyl ammonium chloride hydrate
• Tetrabromophthalic anhydride
• Tetrabutylammonium chloride monohydrate
• Tetrabutylammonium hexafluorophosphate
• Tetramethylammonium borohydride
• TETRAETHYLAMMONIUM BOROHYDRIDE
• Tetrabutylammonium borohydride
• Tetrabutylammonium cyanoborohydride
• trimethylamine cyanoborane