Triethylamine

Base Information

• Chemical Name: Triethylamine
• CAS No.: 121-44-8
• Deprecated CAS: 144514-14-7,168277-99-4,172227-74-6,449752-61-8,750564-56-8,1200828-44-9,1633017-83-0,2011746-49-7,1200828-44-9,168277-99-4,172227-74-6,750564-56-8
• Molecular Formula: C6H15N
• Molecular Weight: 101.192
• Hs Code.: H5)3 MOL WT. 101.19
• European Community (EC) Number: 204-469-4
• ICSC Number: 0203
• UN Number: 1296
• UNII: VOU728O6AY
• DSSTox Substance ID: DTXSID3024366
• Nikkaji Number: J2.485F
• Wikipedia: Triethylamine
• Wikidata: Q139199
• RXCUI: 1307097
• Metabolomics Workbench ID: 45587
• ChEMBL ID: CHEMBL284057
• Mol file: 121-44-8.mol

Synonyms:triethylamine;triethylamine acetate;triethylamine dinitrate;triethylamine hydrobromide;triethylamine hydrochloride;triethylamine maleate (1:1);triethylamine phosphate;triethylamine phosphate (1:1);triethylamine phosphonate (1:1);triethylamine sulfate;triethylamine sulfate (2:1);triethylamine sulfite (1:1);triethylamine sulfite (2:1);triethylammonium formate

Chemical Property of Triethylamine

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 51.75 mm Hg ( 20 °C)
• Melting Point: -115 °C
• Refractive Index: n20/D 1.401(lit.)
• Boiling Point: 90.495 °C at 760 mmHg
• PKA: 10.75(at 25℃)
• Flash Point: 20°F
• PSA: 3.24000
• Density: 0.75 g/cm³
• LogP: 1.34810
• Storage Temp.: 2-8°C
• Solubility.: water: soluble112g/L at 20°C
• Water Solubility.: 133 g/L (20 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 101.120449483
• Heavy Atom Count: 7
• Complexity: 25.7
• Transport DOT Label: Flammable Liquid Corrosive

Purity/Quality:

98% ^*data from raw suppliers

Triethylamine 99.5+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Statements: 11-20/21/22-35
• Safety Statements: 3-16-26-29-36/37/39-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aliphatic
• Canonical SMILES: CCN(CC)CC
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema. The effects may be delayed. Medical observation is indicated. The substance may cause effects on the central nervous system.
• Uses: Triethylamine is a clear, colorless liquid with an Ammonia or fish-like odor. It is used in making waterproofing agents, and as a catalyst, corrosion inhibitor and propellant. It is mainly used as base, catalyst, solvent and raw material in organic synthesis and is generally abbreviated as Et3N, NEt3 or TEA. It can be used to prepare phosgene polycarbonate catalyst, polymerization inhibitor of tetrafluoroethylene, rubber vulcanization accelerator, special solvent in paint remover, enamel anti-hardener, surfactant, antiseptic, wetting agent, bactericides, ion exchange resins, dyes, fragrances, pharmaceuticals, high-energy fuels, and liquid rocket propellants, as a curing and hardening agent for polymers and for the desalination of seawater. Consumption Quota of in medical industry: ▼▲ Medicine Consumption Quota(Unit: t/t) Ampicillin sodium 0.465 Amoxicillin 0.391 Cefazolin sodium 2.442 Cefazolin organism 1.093 Oxygen piperazine penicillin 0.584 Ketoconazole 8.00 Vitamin B6 0.502 Fluorine organism acid 10.00 Praziquantel 0.667 Thiotepa 1.970 Penicillamine 1.290 Berberine hydrochloride 0.030 Verapamil 0.540 Alprazolam 3.950 Adjacent benzene acetic acid 0.010 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 neutralizers 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 the automotive casting industry and the textile industry.
• Physical properties: Clear, colorless to light yellow flammable liquid with a strong, penetrating, ammonia-like odor. Experimentally determined detection and recognition odor threshold concentrations were <400 μg/m3 (<100 ppbv) and 1.1 mg/m3 (270 ppbv), respectively (Hellman and Small, 1974). An odor threshold concentration of 0.032 ppbv was determined by a triangular odor bag method (Nagata and Takeuchi, 1990).

Technology Process of Triethylamine

There total 417 articles about Triethylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.7%

ethylamine (75-04-7,85404-22-4) + N-butylamine (109-73-9,85404-21-3) → tributyl-amine (102-82-9) + N-ethylbutylamine (13360-63-9) + N,N-diethylbutylamine (4444-68-2) + di-n-butylethylamine (4458-33-7) + dibutylamine (111-92-2) + diethylamine (109-89-7) + triethylamine (121-44-8)

Guidance literature:

With hydrogen; at 200 ℃; under 6000.6 Torr; Reagent/catalyst; Temperature;

DOI:10.1007/s11164-012-0790-8

Reference yield: 48.0%

N-chlorodiethylamine (5775-33-7) + ethyl N,N'-tetraethyldiamidophosphite (2632-88-4) → hexaethylphosphorous triamide (2622-07-3) + tetraethyldiamidochlorophosphate (1794-24-7) + chloroethane (75-00-3) + triethylamine (121-44-8)

Guidance literature:

In Petroleum ether; Mechanism; Ambient temperature; also other solvent (CH₂Cl₂) used; also the tert-butyl ester investigated;

Reference yield:

p-nitrophenol-triethylamine complex (proton-transfer complex) (15852-96-7) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + triethylamine (121-44-8)

Guidance literature:

In acetonitrile; at 25 ℃; Rate constant; Equilibrium constant;

DOI:10.1021/j150615a026

upstream raw materials:

2,2,6,6-Tetramethyl-4-piperidone

diethyl ether

ethyl iodide

ethyl bromide

Downstream raw materials:

2-diazo-acetophenone

2-chloro-1-(2-chloromethyl-phenyl)-ethanone

2-bromo-1-(2-bromomethyl-phenyl)-ethanone

1-benzoyl-2-thioxo-imidazolidin-4-one

Refernces

• 1、 Chiavarino, Barbara,Cipollini, Romano,Crestoni, Maria Elisa,Fornarini, Simonetta,Lanucara, Francesco,Lapi, Andrea. "Probing the compound I-like reactivity of a bare high-valent oxo iron porphyrin complex: The oxidation of tertiary amines". . p. 3208 - 3217. Retrieved 2008.
• 2、 Shamma et al.. "-". . p. 1375. Retrieved 1966.
• 3、 Connelly Robinson, Samantha J.,Zall, Christopher M.,Miller, Deanna L.,Linehan, John C.,Appel, Aaron M.. "Solvent influence on the thermodynamics for hydride transfer from bis(diphosphine) complexes of nickel". . p. 10017 - 10023. Retrieved 2016.
• 4、 Kelly,Smith. "". . p. 329. Retrieved 1978.
• 5、 Cowley,Mills. "". . p. 2911. Retrieved 1969.
• 6、 Preti, Debora,Squarcialupi, Sergio,Fachinetti, Giuseppe. "Production of hcooh/net3 adducts by co2/h2 incorporation into neat NEt3". . p. 2581 - 2584. Retrieved 2010.
• 7、 Chen, Zuxing,Yang, Guichun,Zhang, Zhaojun. "Soluble polymer-supported synthesis of tertiary amines". . p. 729 - 734. Retrieved 2003.
• 8、 Kanemoto, Akihiko,Niizuma, Sigeya,Konishi, Siro,Kokubun, Hiroshi. "CIDEP Study of Durosemiquinone Radical in Various Solvents". . p. 46 - 50. Retrieved 1983.
• 9、 Buckley, Eric,Everard, John E.,Wells, Clifford H. J.. "Studies on nitroaromatic compounds. Part 8. A kinetic and spectroscopic study of the reaction of di- and tri-ethylamine with 1,5-dimethyl-2,4,8- trinitronaphthalene". . p. 132 - 138. Retrieved 1980.
• 10、 Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong. "Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application". . p. 2059 - 2067. Retrieved 2021/09/02.