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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)

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

Signal Word

Warning

Hazard Statements

H312,H315,H319,H411

Hazard Classifications

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

Storage Class Code

10 - Combustible liquids

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)

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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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)
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.
Soon-Sun Hong et al.
Archives of pharmacal research, 28(3), 330-334 (2005-04-19)
The effect of a new hepatoprotective agent, YH-439, on the hepatobiliary transport of a model organic cation (OC), TBuMA (tributylmethylammonium), was investigated. The area under the plasma concentration-time curve (AUC) from time zero to 4 h following iv administration of
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
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