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Sigma-Aldrich

Tetrabutylammonium chloride

greener alternative

≥97.0% (NT)

Synonym(s):

N,N,N-tributyl-butanaminium chloride

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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
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sustainability

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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

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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

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’.

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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
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
Chao Zhong et al.
Carbohydrate polymers, 94(1), 38-45 (2013-04-03)
In this article, a novel and high efficient solvent, tetra-n-Butylammonium Hydroxide (TBAH), was used for dissolution and isolation of straw cellulose from wheat straw. The composition analysis with gas chromatography (GC) and the spectroscopic characterization analysis conducted by X-Ray diffraction
R Bryan Sears et al.
Journal of inorganic biochemistry, 121, 77-87 (2013-01-29)
The complex cis-[Ru(phpy)(phen)(CH3CN)2](+) (phpy=2-phenylpyridine, phen=1,10-phenanthroline) was investigated as a potential photodynamic therapy (PDT) agent. This complex presents desirable photochemical characteristics including a low energy absorption tail extending into the PDT window (600-850nm) and photoinduced exchange of the CH3CN ligands, generating
Oliver Bixner et al.
The Journal of chemical physics, 136(20), 204503-204503 (2012-06-07)
The interaction of exciton and charge transfer (CT) states plays a central role in photo-induced CT processes in chemistry, biology, and physics. In this work, we use a combination of two-dimensional electronic spectroscopy (2D-ES), pump-probe measurements, and quantum chemistry to
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