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228982

Sigma-Aldrich

Benzyltrimethylammonium chloride

97%

Synonym(s):

Amberlite IRC 178(Cl), Benzyltrimethylammonium chloride (6CI), Trimethylbenzylammonium chloride

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About This Item

Linear Formula:
C6H5CH2N(Cl)(CH3)3
CAS Number:
56-93-9
Molecular Weight:
185.69
Beilstein:
3917255
EC Number:
200-300-3
MDL number:
MFCD00011782
UNSPSC Code:
12352107
PubChem Substance ID:
24853719
NACRES:
NA.22

Assay

97%

mp

239 °C (dec.) (lit.)

SMILES string

[Cl-].C[N+](C)(C)Cc1ccccc1

InChI

1S/C10H16N.ClH/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H/q+1;/p-1

InChI key

KXHPPCXNWTUNSB-UHFFFAOYSA-M

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Application

Benzyltrimethylammonium chloride can be used as a phase catalyst in:
  • The synthesis of alkyl and aryl sulfonamides from thiols and disulfides in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCH).
  • The selective oxidation of benzyl alcohol to benzaldehyde using hydrogen peroxide as oxidant.
  • The esterification reaction of ethanol and lauric acid.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Muta. 2

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Selective oxidation of benzyl alcohol with hydrogen peroxide over reaction-controlled phase-transfer catalyst
Weng Z, et al.
Catalysis Communications, 8(10), 1493-1496 (2007)
Kinetics of the reaction of ethanol and lauric acid catalyzed by deep eutectic solvent based on benzyltrimethylammonium chloride
Li Kun, et al.
The Canadian Journal of Chemical Engineering, 97(5), 1144-1151 (2019)
Convenient one-pot Synthesis of sulfonamides from thiols and disulfides using 1, 3-dichloro-5, 5-dimethylhydantoin (DCH)
Veisi Hojat
Bull. Korean Chem. Soc., 33(2), 383-386 (2012)
Kathrin Müller et al.
Analytical and bioanalytical chemistry, 412(20), 4867-4879 (2020-03-05)
Matrix effects have been shown to be very pronounced and highly variable in the analysis of mobile chemicals, which may severely exacerbate accurate quantification. These matrix effects, however, are still scarcely studied in combination with hydrophilic interaction liquid chromatography (HILIC)
Purushothaman Gopinath et al.
The Journal of organic chemistry, 74(16), 6291-6294 (2009-07-22)
An efficient protocol is reported for the synthesis of thioesters from carboxylic acids with use of acyloxy phosphonium salts as intermediates and benzyltriethylammonium tetrathiomolybdate as the sulfur transfer reagent.
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