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56-37-1 - Benzyltriethylammonium chloride, 99% - BTEAC - TEBA - A13268 - Alfa Aesar

A13268 Benzyltriethylammonium chloride, 99%

CAS Number
56-37-1
Synonyms
BTEAC
TEBA

Size Price ($) Quantity Availability
100g 30.69
500g 94.55
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Benzyltriethylammonium chloride, 99%

MDL
MFCD00011824
EINECS
200-270-1

Chemical Properties

Formula
(CH3CH2)3N(CH2C6H5)Cl
Formula Weight
227.78
Melting point
ca 190° dec.
Sensitivity
Hygroscopic
Solubility
Soluble in acetone, alcohol and water. Insoluble in ether.

Applications

Benzyltriethylammonium chloride is used as a catalyst in the preparation of 2-phenylbutyronitrile from phenyl acetonitrile. It is involved in the Knoevenagel condensation of carbonyl compounds with active methylene compounds to give olefinic products. It acts as a phase transfer catalyst used in the alkylation reaction. It reacts with 1H-Pyridine-2-thione to get 2-Benzylsulfanyl-pyridine.

Notes

Store in cool place. Hygroscopic. Incompatible with strong oxidizing agents.

Literature References

Phase-transfer catalyst (see Appendix 2) which has found wide application in the generation of carbenes from haloforms and related precursors: Org. Synth. Coll., 7, 12 (1990); 8, 223 (1993). Dihalocarbenes have been used to convert primary amines (t-butylamine) to isonitriles: Org. Synth. Coll., 6, 232 (1988), and in the dehydration of amides, thioamides and oximes to nitriles: Tetrahedron Lett., 2121 (1973). Ureas give cyanamides.

For use in the formation of polysubstituted cyclopropanes by carbene-type addition to double bonds, see Ethyl­ chloroacetate, A15554.

For use in the dialkylation of malonate esters to give cyclopropane derivatives, see: Synthesis, 54 (1985); Org. Synth. Coll., 7, 411 (1993).

In combination with NaBr in acetonitrile, has been used for the mono-dealkylation of phosphonate diesters: Synthesis, 453 (1983).

Ramos, M. D.; Gomez, G. I. G.; Gonzalez, N. S. Immobilization of Candida rugosa lipase on bentonite modified with benzyltriethylammonium chloride. J. Mol. Catal. B: Enzym. 2014, 99, 79-84.

Wu, Y. C.; Leowanawat, P.; Sun, H. J.; Partridge, B. E.; Peterca, M.; Graf, R.; Spiess, H. W.; Zeng, X.; Ungar, G.; Hsu, C. S.; Heiney, P. A.; Percec, V. Complex Columnar Hexagonal Polymorphism in Supramolecular Assemblies of a Semifluorinated Electron-Accepting Naphthalene Bisimide. J. Am. Chem. Soc. 2015, 137 (2), 807-819.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335-H303

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May be harmful if swallowed.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
3574984
Harmonized Tariff Code
2923.90
TSCA
Yes
RTECS
BO8275000

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