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Sigma-Aldrich

Tetrabutylammonium hydroxide solution

greener alternative

40 wt. % in H2O

Synonym(s):

N,N,N-Tributyl-1-butanaminium hydroxide, TBAH 40, Tetra-n-butylammonium hydroxide

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(OH)
CAS Number:
2052-49-5
Molecular Weight:
259.47
Beilstein/REAXYS Number:
3571228
MDL number:
MFCD00009425
UNSPSC Code:
12352100
PubChem Substance ID:
24850769
NACRES:
NA.21

form

liquid

Quality Level

200

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

concentration

40 wt. % in H2O

refractive index

n20/D 1.405

density

0.99 g/mL at 25 °C

greener alternative category

Aligned,

SMILES string

[OH-].CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H2/q+1;/p-1

InChI key

VDZOOKBUILJEDG-UHFFFAOYSA-M

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General description

Tetrabutylammonium hydroxide is a quaternary ammonium salt mainly used as a strong base and phase-transfer catalyst. It can be synthesized from tetrabutylammonium iodide.
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Application

Tetrabutylammonium hydroxide solution (TBAOH) may be used in the following studies:
  • For the dissolution of 10wt% cellulose under room temperature conditions.
  • As a catalyst during the synthesis of 1,2,4-oxadiazoles.
  • Preparation of TBAOH salts of fatty acids.

Caution

May crystallize below 30°C
Gentle warming and swirling should redissolve the solid

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1 - Skin Sens. 1

Storage Class

8B - Non-combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Tetrabutylammonium Hydroxide
Bos ME.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
Tetrabutylammonium Hydroxide as Titrant for Acids in Nonaqueous Solutions.
Cundiff RH and Markunas PC.
Analytical Chemistry, 28(5), 792-797 (1956)
Construction of 3, 5-substituted 1, 2, 4-oxadiazole rings triggered by tetrabutylammonium hydroxide: a highly efficient and fluoride-free ring closure reaction of O-acylamidoximes.
Otaka H, et al.
Tetrahedron Letters, 55(5), 979-981 (2014)
B B Y Lau et al.
Bioresource technology, 197, 252-259 (2015-09-08)
Aqueous solutions of tetrabutylphosphonium hydroxide have been evaluated as pretreatment media for rice husks, prior to sulphuric acid hydrolysis or cellulase enzymatic hydrolysis. Varying the water:tetrabutylphosphonium hydroxide ratio varied the rate of delignification, as well as silica, lignin and cellulose
Foaming and emulsifying properties of fatty acids neutralized by tetrabutylammonium hydroxide.
Fameau AL, et al.
Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 403, 87-95 (2012)
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