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70444

Sigma-Aldrich

Tributylmethylammonium chloride

≥98.0% (T)

Synonym(s):

Methyltributylammonium chloride

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About This Item

Linear Formula:
(CH3CH2CH2CH2)3N(Cl)CH3
CAS Number:
Molecular Weight:
235.84
Beilstein:
6300212
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.0% (T)

form

crystals

SMILES string

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

InChI

1S/C13H30N.ClH/c1-5-8-11-14(4,12-9-6-2)13-10-7-3;/h5-13H2,1-4H3;1H/q+1;/p-1

InChI key

IPILPUZVTYHGIL-UHFFFAOYSA-M

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General description

Tributylmethylammonium chloride is a quaternary ammonium salt commonly used as a catalyst in the synthesis of ɛ-caprolactone and 1-substituted tetrazoles.

Application

Tributylmethylammonium chloride can be used as a phase transfer catalyst in the synthesis of ɛ-caprolactone by Baeyer-Villiger oxidation of cyclohexanone in the presence of KHSO5 as an oxidizing agent.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Dermal - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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One-pot synthesis of 1-substituted 1 H-1, 2, 3, 4-tetrazoles from 2aminothiazoles using tributylmethylammonium chloride as a catalyst
Nagaraju K, et al
Heterocyclic Communications, 23(5), 365-368 (2017)
New and efficient technique for the synthesis of ?-caprolactone using KHSO5 as an oxidising agent in the presence of a phase transfer catalyst
Baj S, et al
Applied Catalysis A: General, 395(1-2), 49-52 (2011)
R H Moseley et al.
The Journal of pharmacology and experimental therapeutics, 276(2), 561-567 (1996-02-01)
Hepatic organic cation transport in vitro, using tetraethylammonium (TEA) as a substrate, consists of at least two steps: sinusoidal uptake is stimulated by an inside-negative membrane potential and canalicular membrane transport is mediated by organic cation:H+ exchange (Moseley et al.
D M Kou et al.
Se pu = Chinese journal of chromatography, 17(6), 550-552 (2003-01-30)
In this paper, use of tri-n-butylammonium dodecylsulfonate as liquid phase to prepare a capillary column suitable to separate carboxylic acids in a direct injection mode, by the method of dynamic coating with mercury plug, is reported. The results showed that
Moon Kyoung Kim et al.
Journal of pharmaceutical sciences, 94(12), 2644-2655 (2005-11-01)
The oral bioavailability of tributylmethyl ammonium (TBuMA), an organic cation (OC), exhibited a dose-dependency (i.e., 17, 27, and 35% at doses of 0.4, 4, or 12 micromol/kg, respectively) in the rat. Relevant mechanisms were investigated in the present study by

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