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Triethylamine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds. It acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizer for condensation reactions and Swern oxidations. It finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier. It is also used as an accelerator activator for rubber, as a propellant, as a corrosion inhibitor, as a curing and hardening agent for polymers and for the desalination of seawater. Furthermore, it is used in automotive casting industry and textile industry.
The apparent base strength of triethylamine has been increased by its use in combination with certain metal salts, examined by Rathke. For the acylation of malonic esters with acyl chlorides, MgCl2 was found to be effective, whereas other metal salts had no effect: J. Org. Chem., 50, 2622 (1985); Synth. Commun., 15, 1039 (1985); Tetrahedron, 48, 9233 (1993). For the Horner-Wadsworth-Emmons olefination reaction, LiBr or LiCl gave the best results under most conditions, although Mg salts showed some effect; other metal salts were ineffective: J. Org. Chem., 50, 2624 (1985).
Addition of triethylamine enables the reaction of Grignard reagents with esters to be interrupted at the ketone stage. Deuterium-labelling shows that this is caused by enolization of the ketone. Good yields are obtained unless the ester itself is readily enolized: Synthesis, 877 (1980).
Murahashi, S. I.; Zhang, D.; Iida, H.; Miyawaki, T.; Uenaka, M.; Murano, K.; Meguro, K. Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine. Chem. Commun. 2014, 50 (71), 10295-10298.
Soni, R.; Hall, T. H.; Mitchell, B. P.; Owen, M. R.; Wills, M. Asymmetric reduction of electron-rich ketones with tethered ru(II)/TsDPEN catalysts using formic acid/triethylamine or aqueous sodium formate. J. Org. Chem. 2015, 80 (13), 6784-6793.
Hazard Statements: H225-H302-H311-H314-H331-H335-H336
Highly flammable liquid and vapour. Harmful if swallowed. Toxic in contact with skin. Causes severe skin burns and eye damage. Toxic if inhaled. May cause respiratory irritation. May cause drowsiness or dizziness.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant