121-44-8

Basic information

• Product Name: Triethylamine
• Synonyms: (C2H5)3N;(Diethylamino)ethane;ai3-15425;Ethanamine, N,N-diethyl-;ethanamine,n,n-diethyl-;N,N,N-Triethylamine;N,N-Diethylethanamin;n,n-diethyl-ethanamin
• CAS NO: 121-44-8
• Molecular Formula: C₆H₁₅N
• Molecular Weight: 101.19
• EINECS: 204-469-4
• Product Categories: Intermediates of Dyes and Pigments;Intermediates;Analytical Reagents for General Use;Puriss p.a.;T-Z, Puriss p.a.;Amino Acid Analysis ReagentsChemical Synthesis;Organic BasesAmino Acid Analysis;Regents for amino acid analysis;Amino Acid Analysis;Peptide Analysis and Characterization;Reagents for amino acid derivatisation&detection;Organic BasesProtein Structural Analysis;Protein Sequencing;Reagents for Protein Sequencing;Chemical Synthesis;Organic Bases;Synthetic Reagents;Reagent PlusDerivatization Reagents TLC;Essential Chemicals;Routine Reagents;TLC Reagents, S-Z;TLC Visualization Reagents (alphabetic sort);HPLC;HPLC Buffer;HPLC Buffers;HPLC Buffers - SolutionChromatography/CE Reagents;Solution;LC-MS Additives;Mass Spectrometry (MS)&LC-MS;Spectroscopy;Alphabetical;Biological Buffers;BioUltra Buffers;LEDA HPLC;HPLC and LCMS Mobile Phase Additive
• Mol File: 121-44-8.mol
• Article Data: 339

Chemical Properties

• Melting Point: -115 °C
• Boiling Point: 90 °C
• Flash Point: 20 °F
• Appearance: Clear/Liquid
• Density: 0.728
• Vapor Density: 3.5 (vs air)
• Vapor Pressure: 51.75 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.401(lit.)
• Storage Temp.: 2-8°C
• Solubility: water: soluble112g/L at 20°C
• PKA: 10.75(at 25℃)
• Explosive Limit: 1.2-9.3%(V)
• Water Solubility: 133 g/L (20 ºC)
• Stability: Stable. Extremely flammable. Readily forms explosive mixtures with air. Note low flash point. Incompatible with strong oxidizing
• Merck: 14,9666
• BRN: 1843166
• CAS DataBase Reference: Triethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Triethylamine(121-44-8)
• EPA Substance Registry System: Triethylamine(121-44-8)

Safety Data

• Hazard Codes: F,C
• Statements: 11-20/21/22-35
• Safety Statements: 3-16-26-29-36/37/39-45-61
• RIDADR: UN 1296 3/PG 2
• WGK Germany: 1
• RTECS: YE0175000
• F: 34
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 121-44-8(Hazardous Substances Data)

Usage

Outline

Triethylamine (formula: C6H15N), also known as N, N-diethylethanamine, is the most simple tri-substituted uniformly tertiary amine, having typical properties of tertiary amines, including salifying, oxidation, Hing Myers test (Hisberg reaction) for triethylamine does not respond. It is colorless to pale yellow transparent liquid, with a strong smell of ammonia, slightly fuming in the air. Boiling point: 89.5 ℃, relative density (water = 1): 0.70, the relative density (Air = 1): 3.48, slightly soluble in water, soluble in alcohol, ether. Aqueous solution is alkaline, flammable. Vapor and air can form explosive mixtures, the explosion limit is 1.2% to 8.0%. It is toxic, with a strong irritant.

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

Production

It is produced by ethanol and ammonia in the presence of hydrogen, in containing Cu-Ni-clay catalyst reactor under heating conditions (190 ± 2 ℃ and 165 ± 2 ℃) reaction. The reaction also produces ethylamine and diethylamine, products were condensed and then absorption by ethanol spray to obtain crude triethylamine, through the final separation, dehydration and fractionation, pure triethylamine is obtained.

Reaction

It can be used to reduce the alkali in the reaction. Alkylation reaction Oxidation reaction

Health Effects

Triethylamine is a flammable liquid and a dangerous fire hazard. It can affect you when inhaled and by passing through the skin. Contact can severely irritate and bum the skin and eyes with possible eye damage. Exposure can irritate the eyes, nose and throat. Inhaling can irritate the lungs. Higher exposures may cause a build-up of fluid in the lungs (pulmonary edema), a medical mergency. It may cause a skin allergy and affect the liver and kidneys.

Chemical Properties

Triethylamine is a colorless to yellowish liquid with a strong ammonia to fish-like odor. It is a base commonly used in organic chemistry to prepare esters and amides from acyl chlorides. Like other tertiary amines,it catalyzes the formation of urethane foams and epoxy resins.

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).

Uses

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.

Application

Triethylamine (TEA, Et3N) is an aliphatic amine. It is used to catalytic solvent in chemical synthesis; accelerator activators for rubber; wetting, penetrating, and waterproofing agents of quaternary ammonium types; curing and hardening of polymers (e.g., corebinding resins); corrosion inhibitor; propellant.Triethylamine has been used during the synthesis of:5′-dimethoxytrityl-5-(fur-2-yl)-2′-deoxyuridine3′-(2-cyanoethyl)diisopropylphosphoramidite-5′-dimethoxytrityl-5-(fur-2-yl)-2′-deoxyuridinepolyethylenimine600-β-cyclodextrin (PEI600-β-CyD)It may be used as a homogeneous catalyst for the preparation of glycerol dicarbonate, via transesterification reaction between glycerol and dimethyl carbonate (DMC).

Production Methods

Triethylamine is prepared by a vapor phase reaction of ammonia with ethanol or reaction of N,N-diethylacetamide with lithium aluminum hydride (Windholz et al 1983). It may also be produced from ethyl chloride and ammonia under heat and pressure (Hawley 1981) or by vapor phase alkylation of ammonia with ethanol (HSDB 1988). U.S. production is estimated at greater than 22,000 tons in 1972 (HSDB 1988).

Definition

ChEBI: Triethylamine is a tertiary amine that is ammonia in which each hydrogen atom is substituted by an ethyl group.

Aroma threshold values

High strength odor, fishy type; recommend smelling in a 0.01% solution or less.

General Description

Triethylamine appears as a clear colorless liquid with a strong ammonia to fish-like odor. Flash point 20°F. Vapors irritate the eyes and mucous membranes. Less dense (6.1 lb / gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen when burned.

Reactivity Profile

Triethylamine reacts violently with oxidizing agents. Reacts with Al and Zn. Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

Vapors irritate nose, throat, and lungs, causing coughing, choking, and difficult breathing. Contact with eyes causes severe burns. Clothing wet with chemical causes skin burns. Triethylamine may also be irritating to skin and mucous membranes (Windholz et al 1983).

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Industrial uses

Triethylamine is used as an anti-livering agent for urea- and melamine-based enamels and in the recovery of gelled paint vehicles (HSDB 1988). It is also used as a catalyst for polyurethane foams, a flux for copper soldering, and as a catalytic solvent in chemical synthesis (Hawley 1981). Triethylamine is used in accelerating activators for rubber; as a corrosion inhibitor for polymers; a propellant; wetting, penetrating, and waterproofing agent of quaternary ammonium compounds; in curing and hardening of polymers (i.e. core-binding resins); and as a catalyst for epoxy resins (Hamilton and Hardy, 1974).

Biochem/physiol Actions

Triethylamine is known to drive polymerization reaction. It acts as a source of carbon and nitrogen for bacterial cultures. Triethylamine is used in pesticides. Triethylamine can serve as an organic solvent.

Safety Profile

Moderately toxic by ingestion and skin contact. Mildly toxic by inhalation. Human systemic effects: visual field changes. Experimental reproductive effects. Mutation data reported. A skin and severe eye irritant. Can cause kidney and liver damage. A very dangerous fire hazard when exposed to heat, flame, or oxidizers. Explosive in the form of vapor when exposed to heat or flame. Complex with dinitrogen tetraoxide explodes below 0°C when undduted with solvent. Exothermic reaction with maleic anhydride above 150°C. Can react with oxidzing materials. Incompatible with N2O4. To fight fire, use CO2, dry chemical, alcohol foam. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

Triethylamine is and aliphatic amine used as a solvent; corrosion inhibitor; in chemical synthesis; and accelerator activators; paint remover; base in methylene chloride or other chlorinated solvents. TEA is used to solubilize 2,4,5-T in water and serves as a selective extractant in the purification of antibiotics. It is used to manufacture quaternary ammonia compounds and octadecyloxymethyltriethylammonium chloride; an agent used in textile treatment.

Carcinogenicity

TEA was not mutagenic in bacterial assays, but it did cause aneuploidy and chromosome aberrations in rats.

Environmental fate

Photolytic. Low et al. (1991) reported that the photooxidation of aqueous tertiary amine solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions. Chemical/Physical. Triethylamine reacted with NOx in the dark to form diethylnitrosamine. In an outdoor chamber, photooxidation by natural sunlight yielded the following products: diethylnitramine, diethylformamide, diethylacetamide, ethylacetamide, diethylhydroxylamine, ozone, acetaldehyde, and peroxyacetyl nitrate (Pitts et al., 1978).

Metabolism

There have been few studies on the metabolism of industrially important aliphatic amines such as triethylamine. It is generally assumed that amines not normally present in the body are metabolized by monoamine oxidase and diamine oxidase (histaminase).Ultimately ammonia is formed and will be converted to urea. The hydrogen peroxide formed is acted upon by catalase and the aldehyde formed is thought to be converted to the corresponding carboxylic acid by the action of aldehyde oxidase (Beard and Noe 1981).

Shipping

UN1296 Triethylamine, Hazard Class: 3; Labels: 3-Flammable liquid, 8-Corrosive material.

Purification Methods

Dry triethylamine with CaSO4, LiAlH4, Linde type 4A molecular sieves, CaH2, KOH, or K2CO3, then distil it, either alone or from BaO, sodium, P2O5 or CaH2. It has also been distilled from zinc dust, under nitrogen. To remove traces of primary and secondary amines, triethylamine has been refluxed with acetic anhydride, benzoic anhydride, phthalic anhydride, then distilled, refluxed with CaH2 (ammonia-free) or KOH (or dried with activated alumina), and again distilled. Another purification method involved refluxing for 2hours with p-toluenesulfonyl chloride, then distilling. Grovenstein and Williams [J Am Chem Soc 83 412 1961] treated triethylamine (500mL) with benzoyl chloride (30mL), filtered off the precipitate, and refluxed the liquid for 1hour with a further 30mL of benzoyl chloride. After cooling, the liquid was filtered, distilled, and allowed to stand for several hours with KOH pellets. It was then refluxed with, and distilled from, stirred molten potassium. Triethylamine has been converted to its hydrochloride (see brlow), crystallised from EtOH (to m 254o), then liberated with aqueous NaOH, dried with solid KOH and distilled from sodium under N2. [Beilstein 4 H 99, 4 I 348, 4 II 593, 4 III 194, 4 IV 322.]

Incompatibilities

A strong base. Violent reaction with strong acids; halogenated compounds; and strong oxidizers. Attacks some forms of plastics, rubber and coatings. Corrosive to aluminum, zinc, copper, and their alloys in the presence of moisture. Reaction with nitrosating agents (e.g., nitrites, nitrous gases, and nitrous acid) capable of releasing carcinogenic nitrosamines.

Waste Disposal

Controlled incineration (incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions).

InChI:InChI=1/C6H15N.H2O4S/c1-4-7(5-2)6-3;1-5(2,3)4/h4-6H2,1-3H3;(H2,1,2,3,4)

Synthetic route

triethylamine N-oxide (2687-45-8) → triethylamine (121-44-8)

Conditions	Yield
With carbon monoxide; 1 wt% Au/TiO2; water In acetone at 60℃; under 7600.51 Torr; for 10h; Autoclave;	99%
With C55H43P3Rh(1+)*C32H12BF24(1-); isopropyl alcohol at 80℃; for 24h; Inert atmosphere;	98%
With titanium tetrachloride; sodium iodide In acetonitrile at 20℃; for 0.0833333h;	55%

3'-(trifluoromethyl)acetophenone (349-76-8) → (R)-1-(3-trifluoromethylphenyl)ethanol (454-91-1, 68120-40-1, 96789-80-9, 127852-24-8) + triethylamine (121-44-8)

Conditions	Yield
	A 99% B n/a

octanol (111-87-5) + ethanol (64-17-5) + acetonitrile (75-05-8) → diethyloctylamine (4088-37-3) + triethylamine (121-44-8)

Conditions	Yield
With hydrogen; copper at 240℃; under 7600 Torr;	A 95% B n/a

ethanol (64-17-5) + 1-Decanol (112-30-1) + acetonitrile (75-05-8) → n-decyldiethylamine (6308-94-7) + triethylamine (121-44-8)

Conditions	Yield
With hydrogen; copper at 240℃; under 7600 Torr;	A 90% B n/a

ethanol (64-17-5) + 1-dodecyl alcohol (112-53-8) + acetonitrile (75-05-8) → diethyllaurylamine (4271-27-6) + triethylamine (121-44-8)

Conditions	Yield
With hydrogen; copper at 240℃; under 7600 Torr;	A 85% B n/a

1,2-bis(dicyanomethylene)-3-triethylammonium cyclopropanide (58608-53-0) + 2,3-Di-piperidin-1-yl-cycloprop-2-eneselone (99968-57-7) → C22H20N6Se + triethylamine (121-44-8)

Conditions	Yield
In dichloromethane for 1h; Heating;	A 84% B n/a

pentadecanol (629-76-5) + ethanol (64-17-5) + acetonitrile (75-05-8) → Diaethyl-pentadecyl-amin (36555-73-4) + triethylamine (121-44-8)

Conditions	Yield
With hydrogen; copper at 240℃; under 7600 Torr;	A 80% B n/a

ethanol (64-17-5) + 1-Hexadecanol (36653-82-4) + acetonitrile (75-05-8) → N,N-diethylhexadecyl tertiary amine (30951-88-3) + triethylamine (121-44-8)

Conditions	Yield
With hydrogen; copper at 240℃; under 7600 Torr;	A 80% B n/a

trichloroisocyanuric acid (87-90-1) → triethylamine (121-44-8)

Conditions	Yield
In dichloromethane	80%

diethylamine (109-89-7) → triethylamine (121-44-8)

Conditions	Yield
With chlorohydridocarbonylbis(tricyclohexylphosphine)ruthenium(II) In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;	79%

ethanol (64-17-5) + tridecan-1-ol (112-70-9) + acetonitrile (75-05-8) → diethyl-tridecyl-amine (66577-48-8) + triethylamine (121-44-8)

Conditions	Yield
With hydrogen; copper at 240℃; under 7600 Torr;	A 78% B n/a

ethanol (64-17-5) + 1-Tetradecanol (112-72-1) + acetonitrile (75-05-8) → N,N-diethyltetradecan-1-amine (7307-58-6) + triethylamine (121-44-8)

Conditions	Yield
With hydrogen; copper at 240℃; under 7600 Torr;	A 77% B n/a

benzyl chloride (100-44-7) + triethylamine (121-44-8) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1)

Conditions	Yield
at 20℃;	100%
In acetonitrile for 1h; Reflux;	95%
	75%

diiodomethane (75-11-6) + triethylamine (121-44-8) → 1-iodo-N,N,N-triethylmethaniminium iodide (104304-17-8)

Conditions	Yield
In acetonitrile at 28℃; under 3750300 Torr; for 19h;	100%
	92%
With hydroquinone In ethyl acetate at 20℃; for 48h; Alkylation;	47.7%
With ethanol at 100℃; im geschlossenen Rohr;

triethylamine (121-44-8) + allyl bromide (106-95-6) → N,N,N-triethylprop-2-en-1-aminium bromide (29443-23-0)

Conditions	Yield
In ethanol at 95℃; for 48h;	100%
for 2h; Reflux;	92%

triethylamine (121-44-8) + methyl iodide (74-88-4) → triethylmethylammonium iodide (994-29-6)

Conditions	Yield
With Hexamethyldisiloxane at 20℃; for 24h; Solvent; Green chemistry;	100%
In butanone at 20℃; Menshutkin reaction;	85%
In methanol; acetonitrile at 30℃; Thermodynamic data; Rate constant; ΔH(excit.), ΔS(excit.); ratio of solvents; transfer enthalpies of activated complex;

1,3-propanesultone (1120-71-4) + triethylamine (121-44-8) → N-(3-sulfonatopropyl)-N,N,N-triethylammonium (1887-93-0)

Conditions	Yield
In toluene at 90℃; for 12h;	100%
In 1,2-dichloro-ethane at 40℃; for 6h;	98.5%
In ethanol at 20℃; for 12h; Inert atmosphere;	96%

piperidine (110-89-4) + carbon disulfide (75-15-0) + triethylamine (121-44-8) → triethylammonium piperidinodithiocarbamate (59983-55-0)

Conditions	Yield
In diethyl ether at 20℃; for 0.2h;	100%
In acetonitrile
In diethyl ether

1-amino-2-naphthol-4-sulfonic acid (116-63-2) + 4-nitrobenzaldehdye (555-16-8) + triethylamine (121-44-8) → triethylammonium 3-hydroxy-4-(4-nitrobenzylidene)amino-1-naphthalenesulfonate

Conditions	Yield
In ethanol for 1h; Heating;	100%

(3-methyl-2-butenyl)trimethoxysilane (72142-16-6) + benzene-1,2-diol (120-80-9) + triethylamine (121-44-8) → triethylammonium bis(catecholato)(3-methyl-2-butenyl)siliconate (114571-77-6)

Conditions	Yield
at 45℃; for 5h;	100%

allyltrimethoxysilane (2551-83-9) + benzene-1,2-diol (120-80-9) + triethylamine (121-44-8) → triethylammonium bis(pyrocatecholato)allylsilicate (114612-18-9)

Conditions	Yield
for 5h; room temperature to 40 deg C;	100%
at 40℃; for 4h; Inert atmosphere; Sealed tube;	55%

(2-methyl-2-propenyl)trimethoxysilane (125715-25-5) + benzene-1,2-diol (120-80-9) + triethylamine (121-44-8) → triethylammonium bis(catecholato)(2-methyl-2-propenyl)siliconate (125715-30-2)

Conditions	Yield
at 45℃; for 5h;	100%

2-Butenyltrimethoxysilane (13436-83-4) + benzene-1,2-diol (120-80-9) + triethylamine (121-44-8) → triethylammonium bis(catecholato)-2-butenylsiliconate

Conditions	Yield
at 45℃; for 5h;	100%

3-(N,N-Dimethylamino)phenyl isocyanate (31125-04-9) + mercaptoacetic acid (68-11-1) + triethylamine (121-44-8) → (3-dimethylaminophenylaminocarbonylthio)acetic acid triethylammonium salt (79479-15-5)

Conditions	Yield
In chloroform for 16h;	100%

trifluoracetyl chloride (354-32-5) + di-H-trifluoroethane-2-sulfonyl fluoride (503-39-9) + triethylamine (121-44-8) → (Z)-1,1,1,4,4,4-Hexafluoro-3-hydroxy-but-2-ene-2-sulfonyl fluoride; compound with triethyl-amine

Conditions	Yield
In diethyl ether at -70 - 20℃;	100%

Chloromethyl pivalate (18997-19-8) + triethylamine (121-44-8) → (2,2-Dimethyl-propionyloxymethyl)-triethyl-ammonium; chloride

Conditions	Yield
In acetonitrile at 70℃;	100%

α-(N-hydroxy)aminoisobutyric acid (5524-45-8) + N-(1-Methyl-2-oxo-ethyl)-2-phenyl-acetamide (127043-29-2) + triethylamine (121-44-8) → C15H20N2O4*C6H15N (130304-14-2)

Conditions	Yield
With 3 A molecular sieve In dichloromethane for 5h; Heating;	100%

methyldichlorophosphane (676-83-5) + triethylamine (121-44-8) → Triethylammonium methylphosphinate (142088-47-9)

Conditions	Yield
With water In acetonitrile at 0℃; for 0.416667h;	100%
With water In acetonitrile at 0℃; for 0.25h;

heptafluorobutyryl chloride (375-16-6) + di-H-trifluoroethane-2-sulfonyl fluoride (503-39-9) + triethylamine (121-44-8) → (Z)-1,1,1,4,4,5,5,6,6,6-Decafluoro-3-hydroxy-hex-2-enesulfonyl fluoride; compound with triethyl-amine

Conditions	Yield
In diethyl ether at -70 - 20℃;	100%

perfluorovaleryl chloride (375-60-0) + di-H-trifluoroethane-2-sulfonyl fluoride (503-39-9) + triethylamine (121-44-8) → (Z)-1,1,1,4,4,5,5,6,6,7,7,7-Dodecafluoro-3-hydroxy-hept-2-enesulfonyl fluoride; compound with triethyl-amine

Conditions	Yield
In diethyl ether at -70 - 20℃;	100%

1,2,2,2-tetrafluoro-ethanesulfonyl fluoride (2127-74-4) + bis(trifluoromethyl)ketene (684-22-0) + triethylamine (121-44-8) → 1,1,1,2,5,5,5-Heptafluoro-3-hydroxy-4-trifluoromethyl-pent-3-enesulfonyl fluoride; compound with triethyl-amine (86797-27-5)

Conditions	Yield
In diethyl ether at -35 - 20℃;	100%

chloromethyl benzoate (5335-05-7) + triethylamine (121-44-8) → <(benzyloxy)methyl>triethylammonium chloride

Conditions	Yield
In acetonitrile at 70℃;	100%

Bis-(phenylsulfonyl)-methyldiphenylphosphinoxid (61368-82-9) + triethylamine (121-44-8) → C25H21O5PS2*C6H15N (83252-97-5)

Conditions	Yield
	100%

Phosphoric acid dihexyl-phosphinoylmethyl ester 2-ethyl-hexyl ester 1-methyl-2-oxo-propyl ester (122417-62-3) + triethylamine (121-44-8) → Phosphoric acid dihexyl-phosphinoylmethyl ester 2-ethyl-hexyl ester; compound with triethyl-amine (129583-08-0)

Conditions	Yield
With pyridine In water at 15℃; for 92h;	100%

methyl 2,6-anhydro-3,8-dideoxy-8-oximino-D-glycero-D-talo-octonate (129908-16-3) + triethylamine (121-44-8) → 2,6-anhydro-3,8-dideoxy-8-oximino-D-glycero-D-talo-octonic acid triethylammonium salt (129908-45-8, 130335-63-6)

Conditions	Yield
With water for 18h; Ambient temperature;	100%

3-Azido-2-cyan-3-(1-ethoxycarbonyl-3-methylthiopropylamino)acrylsaeure-methylester (130148-82-2) + triethylamine (121-44-8) → (E)-2-Cyan-2-<1-(1-ethoxycarbonyl)-3-methylthiopropyl)-4,5-dihydro-1H-tetrazol-5-yliden>essigsaeure-methylester, Triethylammonium-Salz (130149-12-1)

Conditions	Yield
In dichloromethane for 3h; Ambient temperature;	100%

3,3'-<(1-Methoxycarbonyl)-1,5-pentandiyldiimino>bis(3-azido-2-cyanacrylsaeure-methylester) (130149-41-6) + triethylamine (121-44-8) → (E)-2,2'-<<1-(Methoxycarbonyl)-1,5-pentandiyl>di-4,5-dihydro-1H-tetrazol-1-yl-5-yliden>bis(cyanessigsaeure-methylester), Bis(triethylammonium)-Salz (130196-41-7)

Conditions	Yield
In dichloromethane for 3h; Ambient temperature;	100%

3,3'-Dithiobis<(1-methoxycarbonyl)-2,1-ethanediyldiimino>bis(3-azido-2-cyanacrylsaeure-methylester) (130148-87-7) + triethylamine (121-44-8) → (E)-2,2'-Dithio(<1-(methoxycarbonyl)-2,1-ethanediyl>-di-4,5-dihydro-1H-tetrazol-1-yl-5-yliden)bis(cyanessigsaeure-methylester), Bis(triethylammonium)-Salz (130149-22-3)

Conditions	Yield
In dichloromethane for 3h; Ambient temperature;	100%

3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole (76847-41-1) + triethylamine (121-44-8) → triethylamine N-oxide (2687-45-8) + 3-bromo-4,5-dihydro-5-hydroxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole (76847-42-2)

Conditions	Yield
In acetone at 34℃; Rate constant; k2= 2.3E-2M-1sec-1;	A 100% B n/a
In chloroform-d1 at 34℃; Rate constant;	A 100 % Spectr. B n/a

C119H188Br3ClO22P2 (81671-11-6) + triethylamine (121-44-8) → C117H187ClO22P2*C6H15N

Conditions	Yield
With 2,4,6-tri(iso-propyl)benzenesulfonic acid; zinc In pyridine at 40℃; for 0.166667h;	100%

2-picryloxy-3,5-di-tert-butyl phenol (108201-68-9) + 2-picryloxy-4,6-di-tert-butyl phenol (108201-69-0) + triethylamine (121-44-8) → C20H22N3O8(1-)*C6H15N*H(1+)

Conditions	Yield
triethylamine In diethyl ether for 0.166667h; Ambient temperature;	100%

Dithiophosphoric acid O-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[(3-imidazol-1-ylmethyl-phenyl)-bis-(4-methoxy-phenyl)-methoxymethyl]-tetrahydro-furan-3-yl} ester S,S'-diphenyl ester (106502-51-6) + triethylamine (121-44-8) → Thiophosphoric acid O-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[(3-imidazol-1-ylmethyl-phenyl)-bis-(4-methoxy-phenyl)-methoxymethyl]-tetrahydro-furan-3-yl} ester S-phenyl ester; compound with triethyl-amine (106502-57-2)

Conditions	Yield
With pyridine; hypophosphorous acid for 0.166667h;	100%

Upstream product

• 102-71-6 Triethanolamine 
• 109-89-7 Diethylamine 
• 1332-58-7 KAOLIN 
• 1333-74-0 Hydrogen 
• 64-17-5 Etanol 

Downstream Products

• 337904-92-4 5-TERT-BUTOXYCARBONYLAMINO-PYRIDINE-3-CARBOXYLIC ACID 
• 57777-84-1 1-(4-NITROBENZENESULFONYL)-1H-1,2,4-TRIAZOLE 
• 60456-26-0 (R)-Glycidyl butyrate 
• 55512-33-9 Pyridat 
• 67129-08-2 Metazachlor 
• 80756-85-0 S-2-Benzothiazolyl 2-amino-alpha-(methoxyimino)-4-thiazolethiolacetate 
• 37764-25-3 Dichlormid 
• 116-17-6 Triisopropyl phosphite 
• 96989-50-3 DI-2-PYRIDYL THIONOCARBONATE 
• 71-91-0 Tetraethylammonium bromide 
• 112055-34-2 ETHYL 2-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE 
• 59721-28-7 Camostat 
• 111-79-5 Methyl trans-2-nonenoate 
• 16413-26-6 3-Cyanophenyl isocyanate 
• 118753-70-1 N-Boc-N,N-bis(2-chloroethyl)amine 
• 89604-92-2 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate 
• 31009-34-4 6-FLUORO-4-HYDROXY-2-(TRIFLUOROMETHYL)QUINOLINE 
• 404-71-7 3-FLUOROPHENYL ISOCYANATE 
• 3710-84-7 N,N-Diethylhydroxylamine 
• 2048-57-9 2-Thienyl isocyanate 
• 69922-28-7 3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE 
• 16744-98-2 2-FLUOROPHENYL ISOCYANATE 
• 7177-48-2 Ampicillin 
• 137076-54-1 TRI-TERT-BUTYL 1 4 7 10-TETRAAZACYCLODOD 
• 85801-02-1 indomethacin farnesil 
• 1195-45-5 4-Fluorophenyl isocyanate 
• 7039-50-1 2-amino-5-chloro-diphenyl methanol 
• 161233-97-2 2-CYANO-4-PYRIDINE CARBOXYLIC ACID 
• 4651-81-4 Methyl 2-aminothiophene-3-carboxylate 
• 61727-33-1 5-Chloro-2-(methylthio)pyrimidine-4-carboxylic acid 
• 42097-42-7 3-Hydroxy-6-methyl-2-pyridinemethanol 
• 5416-93-3 4-Methoxyphenyl isocyanate 
• 227958-47-6 METHYL 3-[(2-BROMOACETYL)AMINO]THIOPHENE-2-CARBOXYLATE 
• 111080-65-0 4-(BOC-AMINOMETHYL)PYRIDINE 
• 3320-83-0 2-Chlorophenyl isocyanate 
• 40465-45-0 4-Cyanophenyl isocyanate 
• 700-87-8 2-Methoxyphenyl isocyanate 

Recommend Products

• 10022-13-6  1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 31505-46-1  tetra-O-acetyl-2-(2-carboxy-benzoylamino)-2-deoxy-β-D-glucopyranose 
• 67-66-3  chloroform 
• 541-41-3  chloroformic acid ethyl ester 
• 14925-07-6  2,4-bis-aziridin-1-yl-6-methoxy-[1,3,5]triazine 
• 151-56-4  ethyleneimine 
• 3638-04-8  2,4-Dichloro-6-methoxy-1,3,5-triazine 
• 64398-31-8  2,4-bis-aziridin-1-yl-6-chloro-5-phenyl-pyrimidine 
• 1780-39-8  2,4,6-trichloro-5-phenyl-pyrimidine 
• 64440-99-9  4,6-bis-aziridin-1-yl-5-nitro-2-phenyl-pyrimidine 
• 68921-91-5  2-Phenyl-5-nitro-4,6-dichloro-pyrimidine 
• 3282-32-4  2-diazo-acetophenone 
• 186581-53-3  diazomethane 
• 98-88-4  benzoyl chloride 

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