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146552

Sigma-Aldrich

Benzyltriethylammonium chloride

99%

Synonym(s):

BTEAC

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About This Item

Linear Formula:
C6H5CH2N(Cl)(C2H5)3
CAS Number:
56-37-1
Molecular Weight:
227.77
Beilstein:
3574984
EC Number:
200-270-1
MDL number:
MFCD00011824
UNSPSC Code:
12352107
PubChem Substance ID:
24848786
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

mp

190-192 °C (dec.) (lit.)

SMILES string

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

InChI

1S/C13H22N.ClH/c1-4-14(5-2,6-3)12-13-10-8-7-9-11-13;/h7-11H,4-6,12H2,1-3H3;1H/q+1;/p-1

InChI key

HTZCNXWZYVXIMZ-UHFFFAOYSA-M

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Application

Benzyltriethylammonium chloride is a lipophilic phase-transfer catalyst that can be used in phase-transfer catalysis (PTC) to catalyze polycondensation reactions to form high molecular weight polymers under bi-phasic conditions.

It can also be used:
  • To activate hydroxyapatite and natural phosphate for use as a solid support for Knoevenagel condensation and Claisen-Schmidt condensation, respectively at room temperature and in the absence of a solvent.
  • To increase the efficiency of mCPBA oxidation of sulfonimine generated from arenesulfonamide and diethyl acetal of an aromatic aldehyde to form 2-sulfonyloxaziridines.
  • In combination with antimony(V) chloride to form a catalytic system for the Friedel-Crafts acylation reactions of arenes with acyl and sulfonyl chlorides.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

>527.0 °F - closed cup

Flash Point(C)

> 275 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK5660
STBK1996
STBJ8159
STBJ6434
STBH3100

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Phase-Transfer Catalyzed Polycondensation of α,α-Dichloro-p-xylene with 2, 2-Bis (4-hydroxyphenyl) propane
Yamazaki N and Imai Y
Polymer Journal, 15(8), 603-603 (1983)
Antimony (V) Chloride-Benzyltriethylammonium Chloride Complex as an Efficient Catalyst for Friedel- Crafts Acylation Reactions
Huang A-P, et al.
Advanced Synthesis & Catalysis, 346(6), 599-602 (2004)
Chemistry of oxaziridines. 2. Improved synthesis of 2-sulfonyloxaziridines
Davis FA and Stringer OD
The Journal of Organic Chemistry, 47(9), 1774-1775 (1982)
Polymerization by phase transfer catalysis, 2 Polythiocarbonates by polymerization of Bisphenol A with thiophosgene
Tagle LH, et al.
Macromolecular Chemistry and Physics, 186(5), 915-921 (1985)
Synthesis of aromatic polyphosphonate by phase-transfer catalyzed polycondensation with quaternary onium salts and crown ethers
Imai Y, et al.
Macromolecular Rapid Communications, 1(7), 419-422 (1980)
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