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Sigma-Aldrich

Tributylmethylammonium chloride

≥98.0% (T)

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Synonym(s):
Methyltributylammonium chloride
Linear Formula:
(CH3CH2CH2CH2)3N(Cl)CH3
CAS Number:
56375-79-2
Molecular Weight:
235.84
Beilstein:
6300212
EC Number:
260-135-8
MDL number:
MFCD00011847
UNSPSC Code:
12352116
PubChem Substance ID:
57652249
NACRES:
NA.22

Quality Level

100

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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H312,H315,H319,H411

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
Soon-Sun Hong et al.
Archives of pharmacal research, 29(4), 318-322 (2006-05-10)
Many quaternary ammonium salts are incompletely absorbed after their oral administration and may also be actively secreted into the intestine. However, the underlying mechanism(s) that control the transport of these cations across the intestinal epithelium is not well understood. In
Won-Sik Shim et al.
Archives of pharmacal research, 31(5), 671-677 (2008-05-16)
The effect of organic anionic (OA) fractions of various rat organ tissues on the apparent partition coefficients (APC) of quarternary ammoniums (QAs) between n-octanol and phosphate buffer (pH 7.4) and QAs transport across the LLC-PK1 cell monolayer was examined. The
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
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