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230189

Sigma-Aldrich

Tetrabutylammonium hydroxide solution

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1.0 M in methanol

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:
24853780
NACRES:
NA.21

form

liquid

Quality Level

200

greener alternative product characteristics

Catalysis
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concentration

1.0 M in methanol

refractive index

n20/D 1.3775

density

0.83 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.
Tetrabutylammonium hydroxide solution serves as a phase-transfer catalyst in the transesterification of soybean oil.


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Application

Tetrabutylammonium hydroxide solution (1M in methanol) may be used as a base to synthesize ring methyl and methylene deuteriated porphyrins and metalloporphyrins. It may also be used as an initiator of graft polymerization between pivalolactone and poly(ethylene-co-vinyl acetate-co-methacrylic acid).

Packaging

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Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 1

target_organs

Eyes,Central nervous system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

51.8 °F - closed cup

flash_point_c

11 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0653
STBK4099
STBK2773
STBK3191
STBK0192

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Rapid base-catalyzed deuterium exchange at the ring-adjacent methyl and methylene positions of octaalkyl and natural-derivative porphyrins and metalloporphyrins.
Godziela GM, et al.
Inorganic Chemistry, 25(23), 4286-4288 (1986)
Block and Graft Copolymers of Pivalolactone. 3. Grafts on Ethylene Copolymers
Sundet SA
Macromolecules, 11(1), 146-149 (1978)
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)
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