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Sigma-Aldrich

Tributylmethylammonium chloride solution

75 wt. % in H2O

Synonym(s):

Methyltributylammonium chloride solution

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About This Item

Linear Formula:
CH3N[CH3(CH2)3]3Cl
CAS Number:
56375-79-2
Molecular Weight:
235.84
MDL number:
MFCD00011847
UNSPSC Code:
12352116
PubChem Substance ID:
24855292
NACRES:
NA.22

vapor pressure

7.9 mmHg ( 25 °C)

Quality Level

200

concentration

75 wt. % in H2O

refractive index

n20/D 1.4682

bp

152 °C

density

0.964 g/mL at 25 °C

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

General description

Tributylmethylammonium chloride (TBMAC) is a quaternary ammonium salt commonly used as a phase-transfer catalyst in various organic synthesis reactions. It can also be used in the preparation of ionic liquids.

Application

Tributylmethylammonium chloride solution is 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

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3870
MKCW7145
MKCT0739
MKCT5942
MKCS0454

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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)
Enantioselective biocatalytic reduction of 2 H-1, 4-benzoxazines using imine reductases
Zumbra?gel N, et al.
The Journal of Organic Chemistry, 84(3), 1440-1447 (2018)
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
J W Smit et al.
The Journal of pharmacology and experimental therapeutics, 286(1), 321-327 (1998-07-10)
We recently showed that absence of mdr1-type P-glycoprotein (P-gp) in mice resulted in profoundly reduced hepatic and intestinal clearance of type 1 and type 2 cationic drugs compared with that in wild-type mice. These data strongly support the concept that
Min-Koo Choi et al.
Journal of pharmaceutical sciences, 94(2), 317-326 (2004-12-01)
The in vivo canalicular excretion clearance of tributylmethyl ammonium (TBuMA), a P-glycoprotein (P-gp) substrate, was previously reported to be unaffected by the induction of an experimental hepatic injury (EHI) by CCl(4) despite the increased expression of P-gp in the EHI
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