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246034

Sigma-Aldrich

Benzyltrimethylammonium hydroxide solution

40 wt. % in H2O

Synonym(s):

N,N,N-Trimethyl-N-benzylammonium hydroxide, N,N,N-trimethyl-1-phenylmethanaminium hydroxide, N,N,N-trimethylbenzenemethanaminium hydroxide, Triton B

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About This Item

Linear Formula:
C6H5CH2N(OH)(CH3)3
CAS Number:
100-85-6
Molecular Weight:
167.25
Beilstein/REAXYS Number:
3917256
MDL number:
MFCD00008281
UNSPSC Code:
12352005
PubChem Substance ID:
24854772
NACRES:
NA.22

Quality Level

200

concentration

40 wt. % in H2O

refractive index

n20/D 1.43

density

1.059 g/mL at 25 °C

SMILES string

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

InChI

1S/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1

InChI key

NDKBVBUGCNGSJJ-UHFFFAOYSA-M

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General description

Benzyltrimethylammonium hydroxide solution is used as a phase transfer catalyst. It can assist in situ transesterificaion to synthesize biodiesel.

Application

Benzyltrimethylammonium hydroxide can be used:
  • As a base in the synthesis of activated ynesulfonamides and tertiary enesulfonamides.
  • In the synthesis of 3-indolyl-3-hydroxy oxindoles by treating isatin with indole.
  • As a precursor for the preparation of quaternary ammonium acetate, benzyltrimethylammonium acetate (NBz111AcO). NBz111AcO solution in DMSO can be used to dissolve cellulose.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1A

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Metal-Free Synthesis of Activated Ynesulfonamides and Teritary Enesulfonamides
Andna L and Miesch L
Organic & Biomolecular Chemistry (2019)
Dependence of cellulose dissolution in quaternary ammonium-based ionic liquids/DMSO on the molecular structure of the electrolyte
Kostag M and El Seoud OA
Carbohydrate Polymers, 205(1), 524-532 (2019)
Triton B-Assisted, Efficient, and Convenient Synthesis of 3-Indolyl-3-hydroxy Oxindoles in Aqueous Medium
Meshram HM, et al.
Synthetic Communications, 40(1), 39-45 (2009)
R Daniel Peluffo et al.
The Journal of general physiology, 123(3), 249-263 (2004-02-26)
The effects of organic quaternary amines, tetraethylammonium (TEA) chloride and benzyltriethylammonium (BTEA) chloride, on Na,K pump current were examined in rat cardiac myocytes superfused in extracellular Na(+)-free solutions and whole-cell voltage-clamped with patch electrodes containing a high Na(+)-salt solution. Extracellular
M De Amici et al.
Il Farmaco; edizione scientifica, 42(6), 409-424 (1987-06-01)
The results of a pharmacological investigation on a series of meta-substituted benzyltrimethylammonium salts possessing an antimuscarinic activity are reported. Correlative analysis shows that the pharmacodynamic activity is a function of the hydrophobic-lipophilic parameter associated with the substituent.
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