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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:
56375-79-2
Molecular Weight:
235.84
Beilstein/REAXYS Number:
6300212
EC Number:
260-135-8
MDL number:
MFCD00011847
UNSPSC Code:
12352116
PubChem Substance ID:
57652249
NACRES:
NA.22

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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)
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)
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
I S Song et al.
American journal of physiology. Gastrointestinal and liver physiology, 281(2), G515-G525 (2001-07-12)
The objective of this study was to examine whether ion pair complexation with endogenous bile salts in hepatocytes contributes to the preferential biliary excretion of organic cations (OCs). Tributylmethylammonium (TBuMA; mol wt 200) and triethylmethylammonium (TEMA; mol wt 116) were
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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