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Tetrabutylammonium chloride

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Quaternary ammonium salt of chloride

Tetrabutylammonium chloride
Identifiers

CAS Number	1112-67-0 37451-68-6 Hydrate
3D model (JSmol)	Interactive image
Beilstein Reference	3571227
ChEBI	CHEBI:51988
ChEMBL	ChEMBL1078612
ChemSpider	63847
ECHA InfoCard	100.012.905
EC Number	214-195-7
Gmelin Reference	10839
PubChem CID	70681
CompTox Dashboard(EPA)	DTXSID10883644
InChI 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 Key: NHGXDBSUJJNIRV-UHFFFAOYSA-M
SMILES CCCC[N+](CCCC)(CCCC)CCCC.[Cl-]
Properties
Chemical formula	[(CH₃CH₂CH₂CH₂)₄N]Cl
Molar mass	277.92 g·mol⁻¹
Appearance	white solid
Density	1.018 g/cm³
Melting point	90 °C (194 °F; 363 K)^[1]
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315,H319,H335
Precautionary statements	P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Tetrabutylammonium chloride is theorganic compound with the formula[(CH₃CH₂CH₂CH₂)₄N]⁺Cl⁻, often abbreviated as[Bu₄N]Cl, where Bu stands forn-butyl. A white water-soluble solid, it is aquaternary ammonium salt ofchloride.

It sees use as aphase-transfer catalyst, although it is less popular that the corresponding bromine saltTBAC. It can also undergosalt metathesis reactions to form a variety of othertetrabutylammonium salts.^[2]^[3] Oftentetrabutylammonium bromide is preferred as a source of tetrabutylammonium because it is lesshygroscopic than the chloride.^[4]

References

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^Reichenbach, Judith; Ruddell, Stuart A.; González-Jiménez, Mario; Lemes, Julio; Turton, David A.; France, David J.; Wynne, Klaas (31 May 2017)."Phonon-like Hydrogen-Bond Modes in Protic Ionic Liquids".Journal of the American Chemical Society.139 (21). See bottom of Supporting Information:7160–7163.doi:10.1021/jacs.7b03036.
^Barder, T. J.; Walton, R. A. (1985). "Tetrabutylammonium Octachlorodirhenate(III)".Inorganic Syntheses. Vol. 23. pp. 116–118.doi:10.1002/9780470132548.ch22.ISBN 9780470132548.{{cite book}}:|journal= ignored (help)
^Dilworth, J. R.; Hussain, W.; Hutson, A. J.; Jones, C. J.; McQuillan, F. S. (1997). "Tetrahalo Oxorhenate Anions".Inorganic Syntheses. pp. 257–262.doi:10.1002/9780470132623.ch42.ISBN 9780470132623.
^Klemperer, Walter G. (1990). "Tetrabutylammonium Isopolyoxometalates".Inorganic Syntheses. Vol. 27. pp. 74–85.doi:10.1002/9780470132586.ch15.ISBN 9780470132586.

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