Skip to Content
Merck
CN
All Photos(2)

Documents

86870

Sigma-Aldrich

Tetrabutylammonium chloride

greener alternative

≥97.0% (NT)

Synonym(s):

N,N,N-tributyl-butanaminium chloride

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
[CH3(CH2)3]4NCl
CAS Number:
1112-67-0
Molecular Weight:
277.92
Beilstein:
3571227
EC Number:
214-195-7
MDL number:
MFCD00011635
UNSPSC Code:
12352107
PubChem Substance ID:
57653205
NACRES:
NA.22

Quality Level

200

Assay

≥97.0% (NT)

form

crystals

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

impurities

≤1% water

solubility

H2O: 20 mg/mL, clear, colorless

greener alternative category

, Aligned

SMILES string

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

InChI

1S/C16H36N.ClH/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

NHGXDBSUJJNIRV-UHFFFAOYSA-M

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Tetrabutylammonium chloride is a quaternary ammonium salt that is commonly used as a phase transfer catalyst as well as a source of chloride ions in organic synthesis.

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Application

Tetrabutylammonium chloride (TBACl) can be used as a phase transfer catalyst in the synthesis of:
  • 2-Amino-4H-chromene derivatives by the condensation reaction of aldehydes, malononitrile, and α, or β-naphthol.
  • Methyl esters by esterification reaction of carboxylic acids with dimethyl carbonate in the presence of K2CO3.
It has also been used as an initiator to synthesize 11-trifluoromethylated dibenzodiazepines via cascade radical addition/cyclization of o-isocyanodiaryl amines.

TBACl can also be used with phosphorus pentoxide for greener deoxychlorination.

Process for Producing Halogenated Heteroaryl Compounds

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Efficient and eco-friendly synthesis of 2-amino-4H-chromene derivatives using catalytic amount of tetrabutylammonium chloride (TBAC) in water and solvent-free conditions
Mehrabi H and Kamali N
Journal of the Iranian Chemical Society, 9, 599-605 (2012)
Nancy AlHaddad et al.
Organic & biomolecular chemistry, 17(31), 7330-7336 (2019-07-18)
The present study describes the synthesis of the first phenoxycalix[4]pyrrole-epichlorohydrin based polymer. The advantage of the latter resides in its fast-single step synthesis protocol, low cost, water insolubility and its unexpected anion extraction capacity. The study of this polymer by
Tetrabutylammonium Chloride-Induced Cascade Radical Addition/Cyclization of O-Isocyanodiaryl Amines: A Novel Protocol for the Synthesis of 11-Trifluoromethylated Dibenzodiazepines
Yuan S, et al.
The Journal of Organic Chemistry, 87, 16542-16549 (2022)
Methyl esterification of carboxylic acids with dimethyl carbonate promoted by K2CO3/tetrabutylammonium chloride
Chau K, et al.
Green Chemistry Letters and Reviews, 6, 89-93 (2013)
I P E Macário et al.
Scientific reports, 9(1), 3932-3932 (2019-03-10)
The tailor-made character of deep eutectic solvents (DES) turns them very attractive to be used in several applications, including in health-related areas such as pharmaceutical, nutraceutical, and cosmetic industries. However, although DES has been touted as "green" solvents, several works
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service