TRIETHYLENE DIAMINE

Triethylene Diamine has a role as a catalyst, a reagent and an antioxidant. 
Triethylene Diamine is a bridged compound, a tertiary amino compound, a saturated organic heterobicyclic parent and a diamine.
Triethylene Diamine is an organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. 

CAS Number: 280-57-9
Molecular Formula: C6H12N2
Molecular Weight: 112.17
EINECS Number: 205-999-9

Synonyms: 1,4-Diazabicyclo[2.2.2]octane, Triethylene Diamine, 280-57-9, Dabco, 1,4-DIAZABICYCLO(2.2.2)OCTANE, 1,4-Ethylenepiperazine, Dabco 33LV, Dabco crystal, TEDA, Texacat TD 100, Dabco EG, N,N'-endo-Ethylenepiperazine, 1,4-Diazabicyclo-octane, D 33LV, Thancat TD 33, DTXSID0022016, X8M57R0JS5, NSC-56362, DTXCID902016, CHEBI:151129, RefChem:191536, 205-999-9, Dabco S-25, Triethylene diamine, Dabco R-8020, MFCD00006689, 1,4-diazabicyclo[2,2,2]octane, 1,4-Diaza[2.2.2]bicyclooctane, 1,4-Diazobicyclo(2.2.2)octane, TED, NSC 56362, 1,4-Diazabicyclo [2.2.2] octane, 1,4-diazabicyclo[2.2.2]octane (dabco), 1,4-Diazobicyclo[2.2.2]octane, Bicyclo[2.2.2]-1,4-diazaoctane, 1,4-DIAZABICYCLO-(2,2,2)-OCTANE, Bicyclo(2,2,2)-1,4-diazaoctane, 1,4-diazabicyclo(2.2.2)octane, 1,4-diazobicyclo(2.2.2)octane, 1,4-diazobicyclo[2,2,2]octane, 1,4-diazabicyclo (2.2.2)octane, 1,4-diazabicyclo [2.2.2]octane, 1,4-diazabicyclo(2.2.2) octane, 1,4-diazabicyclo(2.2.2)-octane, 1,4-diazabicyclo[2.2.2] octane, 1,4-diazabicyclo[2.2.2]-octane, 1,4-diazabicyclo (2.2.2) octane, 1,4-diazabicyclo-[2,2,2]-octane, Dabco crystalline, 1,4-diaza-bicyclo[2.2.2]octane, Triethylene-diamine, Tegoamin 33, CAS-280-57-9, CCRIS 6692, HSDB 5556, EINECS 205-999-9, UNII-X8M57R0JS5, AI3-24809, Texacat TD-33, Bicyclo[2.2.2]octane, 1,4-diaza-, 1,4-DIAZABICYCLO-[2.2.2]OCTANE, EC 205-999-9, TEDA-L33, SCHEMBL14938, DABCO(R) 33-LV, Triethylene Diamine;DABCO;TED, SCHEMBL175064, TRIETHYLENEDIAMINE [MI], GTPL2577, orb2940233, SCHEMBL1042294, CHEMBL3183414, 1,4diazabicyclo[2,2,2]octane, TRIETHYLENEDIAMINE [HSDB], 1.4-diazabicyclo[2.2.2]octan, 1,4-Diazabicylo[2.2.2]octane, 1,4 diazabicyclo[2,2,2]octane, 1,4-diazabicyclo-2,2,2-octane, 1,4-diazabicyclo[2,2.21octane, 1,4-diazabicyclo[2.2.21octane, 1,4-Diazabicylco[2,2,2]octane, 1,4- diazabicyclo(2,2,2)octane, 1,4-di azabicyclo[2.2.2]octane, 1,4-diaza bicyclo[2,2,2]octane, 1,4-diaza bicyclo[2.2.2]octane, 1,4-diazabicyclo (2,2,2)octane, 1,4-diazabicyclo-[2,2,2]octane, 1,4-diazabicyclo[2,2,2]-octane, 1,4-diazabicyclo[2.2.2.]octane, HY-Y0566, NSC56362, Tox21_201323, Tox21_302908, 1,4-diazabicyclo (2,2,2) octane, 1,4-diazabicyclo-[2.2.2]-octane, SBB060902, STL185594, 1,4-diaza bicyclo-[2,2.2]-octane, 1,4-diaza-bicyclo-[2,2,2]-octane, AKOS000119052, CS-W020025, FD14322, 1,4-Diazabicyclo(2.2.2)octane 97%, NCGC00249025-01, NCGC00256609-01, NCGC00258875-01, 88935-43-7, BP-13441, PS-11951, D0134, NS00001624, ST50192129, EN300-18991, D70975, F043420, Q423673, F1908-0059, 1,4-Diazabicyclo[2.2.2]octane, ReagentPlus(R), >=99%, 1,4-Diazabicyclo[2.2.2]octane, Vetec(TM) reagent grade, 98%, InChI=1/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H, 1,4-Diaza[2.2.2]bicyclooctane;1,4-diazabicyclooctane;1,4-Diazobicyclo(2.2.2)octane;1,4-diazobicyclo[2.2.2]octane;1,4-Ethylenepiperazine;Bicyclo(2,2,2)-1,4-diazaoctane;o[2.2.2]octane;BACO

Triethylene Diamine also known as DABCO or TEDA, is a highly symmetrical molecule with a cage structure. 
The colorless extremely hygroscopic crystals is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in polymerization and organic synthesis.
Triethylene Diamine is typically used as a catalyst in polymerization reactions. 

Triethylene Diamine, is a bicyclic organic compound with the formula N2(C2H4)3. 
This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in polymerization and organic synthesis.
Triethylene Diamine is similar in structure to quinuclidine, but the latter has one of the nitrogen atoms replaced by a carbon atom. 

Regarding their structures, both DABCO and quinuclidine are unusual in that the methylene hydrogen atoms are eclipsed within each of the three ethylene linkages. 
Furthermore, the Triethylene Diamine rings, of which there are three, adopt the boat conformations, not the usual chair conformations.
Triethylene Diamine, is a caged tertiary diamine commonly used as a strong hindered amine base in chemical synthesis. 

Triethylene Diamine is used in the synthesis of isoxazole derivatives via dehydration of primary nitro compounds in the presence of dipolarophiles. 
It can also be employed as a complexing ligand and as a catalyst.
Triethylene Diamine, also known as 1,4-diazabicyclo[2.2.2]octane, is a solid amine compound at room temperature. 

Triethylene Diamine is a flammable crystal and is easily absorbed in the air. 
The water is deliquescent and easy to rise at room temperature. 
The melting point of Triethylene Diamine is 158°C, but its boiling point is only 174°C, so it is easy to sublime at room temperature. 

The preservation of Triethylene Diamine is very important. 
Triethylene Diamine is easily soluble in water, ethanol, aromatic hydrocarbons and ketones. 
It is easy to combine with carbon dioxide in the air to turn yellow at room temperature, so the color of Triethylene Diamine used in reality is generally pale yellow.

Triethylene Diamine has important uses in the field of fine chemicals, for example, as a catalyst for chemically catalyzing the synthesis of polyurethane rubber and polyurethane coatings. 
Triethylene Diamine is also used to prevent fading caused by free radicals induced by UV radiation fuel, and is widely used in the dye industry. 
At the same time, Triethylene Diamine plays an important role in the agricultural field. 

Triethylene Diamine can be used as an initiator for pesticide production, which makes pesticide production more efficient. 
Triethylene Diamine can also be used as an environmentally friendly cyanide-free electroplating additive, which reduces cyanide The discharge of chemicals causes pollution to the environment. 
In addition, Triethylene Diamine can also be used as a catalyst in curing polymerized epoxy resin, a catalyst for ethylene polymerization, and the like.

Triethylene Diamine plays a very important role in the synthesis of organic polymers, and its market prospect is good.
Triethylene Diamine has a wide range of uses, mainly involving plastic products and industrial applications. 
Among them, in the field of plastics, Triethylene Diamine is used as polyurethane foam, elastomers, plastic products, and molding processes; in industrial applications, it is also a polymer initiator and can be used as various polymerization catalysts, such as ethylene oxide Alkane leech polymerization catalyst. 

In addition, derivatives of Triethylene Diamine can also be used as corrosion inhibitors and emulsifiers; their intermediates can be used to synthesize light-stable materials.
Triethylene diamine, commonly known as 1,4-Diazabicyclo[2.2.2]octane (DABCO), is a bicyclic organic compound containing two nitrogen atoms within a rigid, symmetrical bicyclic framework. 
Its chemical formula is C₆H₁₂N₂, and the structure consists of a six-membered bicyclic ring in which two nitrogen atoms occupy positions 1 and 4, creating a highly basic and nucleophilic environment. 

This rigid bicyclic geometry imparts high thermal and chemical stability to the molecule, making it resistant to degradation under typical laboratory and industrial conditions.
Triethylene diamine is a colorless to pale yellow crystalline solid at room temperature, with a high melting point and low volatility, which makes it relatively easy to handle compared to volatile amines. 

Triethylene Diamine is highly soluble in polar organic solvents such as alcohols, ketones, and dimethylformamide (DMF), while showing limited solubility in nonpolar solvents. 
The presence of two tertiary amine groups gives DABCO strong nucleophilic and basic properties, which enable it to react efficiently with a wide variety of electrophilic compounds, including epoxides, carbonyls, and acid chlorides.

Melting point: 156-159 °C(lit.)
Boiling point: 174 °C
Density: 1.02 g/mL
Bulk density: 800 kg/m³
Vapor pressure: 2.9 mm Hg (50 °C)
Refractive index: n20/D 1.4634(lit.)
Flash point: 198 °F
Storage temp.: Store below +30°C
Solubility: 400 g/l
Form: Hygroscopic Crystals
pKa: 3.0, 8.7 (at 25℃)
Color: White to pale yellow
Water Solubility: 46 g/100 mL (26 ºC)
Sensitive: Hygroscopic
Merck: 14,9669
BRN: 103618
Stability: Stable, but very hygroscopic. Incompatible with strong oxidizing agents, strong acids. Highly flammable.
LogP: -0.49 at 20℃

Triethylene diamine can be produced from ethylenediamine or ethanolamine, diethanolamine, or diethylenetriamine with a variety of different catalysts.
Triethylene diamine reacts virtually quantitatively with bromine to give a 1/1 adduct. 
With alkyl halides it forms quaternary salts, even in nonpolar solvents. 

Apart from its highly nucleophilic nature, Triethylene Diamine exhibits catalytic activity in base-catalyzed reactions.
The pKa of [HDABCO]+ (the protonated derivative) is 8.8, which is almost the same as ordinary alkylamines. 
The nucleophilicity of the amine is high because the amine centers are unhindered. 

Triethylene diamine is sufficiently basic to promote a variety of coupling reactions.
The reagent Selectfluor is derived by alkylation of DABCO with dichloromethane following by treatment with fluorine. 
A colourless salt that tolerates air, Selectfluor has been commercialized for use for electrophilic fluorination.

As an unhindered amine, Triethylene diamine is a strong ligand and Lewis base. 
Triethylene diamine forms a crystalline 2:1 adduct with hydrogen peroxide and sulfur dioxide.
Triethylene diamine and related amines are quenchers of singlet oxygen and effective antioxidants, and can be used to improve the lifetime of dyes. 

This makes Triethylene diamine useful in dye lasers and in mounting samples for fluorescence microscopy (when used with glycerol and PBS).
Triethylene diamine can also be used to demethylate quaternary ammonium salts by heating in dimethylformamide (DMF).
Triethylene diamine is widely used as a catalyst, ligand, and base in organic synthesis. 

Its bicyclic structure prevents extensive steric hindrance around the nitrogen atoms, allowing them to interact readily with reactants, yet the rigidity of the ring maintains stereochemical control in certain reactions. 
Triethylene diamine is frequently employed in polyurethane and epoxy resin chemistry as a catalyst for polymerization reactions, where it accelerates the formation of urethane or epoxy linkages without being consumed, providing both high efficiency and reusability.

In addition to its catalytic applications, triethylene diamine serves as a building block for specialty chemicals, including quaternary ammonium salts, chelating agents, and organocatalysts.
Triethylene diamines strong basicity and nucleophilicity also make it useful in phase-transfer catalysis, gas absorption processes, and other industrial chemical reactions where controlled nucleophilic activity is essential.

From a safety perspective, Triethylene diamine is generally considered moderately hazardous, with potential risks upon skin or eye contact and inhalation of dust, but it is far less reactive and dangerous than highly pyrophoric organoboron or halogenated compounds. 
Its stability, strong catalytic activity, and ability to facilitate a broad range of chemical transformations have made triethylene diamine an indispensable reagent in organic synthesis, polymer chemistry, and industrial chemical production.

Uses:
Triethylene diamine an anti-fade reagent shown to scavenge free-radicals due to flurochrome excitation.
Triethylene diamine is used as polyurethane catalyst, Balis-Hillman reaction catalyst complexing ligand and lewis base. 
Triethylene diamine finds use in dye lasers and in mounting samples for fluorescence microscopy and as anti-fade reagent shown to scavenge free radicals due to flurochrome excitation of fluorochromes. 

Triethylene diamine is an oxidation and polymerization catalyst.
Triethylene diamine is a versatile, highly reactive bicyclic amine used as a catalyst in polyurethane and epoxy resin production, a phase-transfer catalyst in organic synthesis, a precursor for specialty chemicals, and an agent in gas absorption processes. 
Its strong nucleophilicity, bicyclic rigidity, and thermal stability make it invaluable in both industrial manufacturing and laboratory research, enabling efficient reactions, precise polymer control, and the synthesis of advanced materials.

Triethylene diamine is used as a nucleophilic catalyst for: formation of polyurethane from alcohol and isocyanate functionalized monomers and pre-polymers.
Baylis–Hillman reactions of aldehydes and unsaturated ketones and aldehydes.
In chemical and biological defense, activated carbon is impregnated with DABCO for use in filters for masks, collective protection systems, and the like.

Triethylene diamine is extensively used as a highly effective catalyst in the production of polyurethanes, where it facilitates the reaction between isocyanates and polyols to form urethane linkages. 
Its bicyclic amine structure allows it to accelerate the polymerization reaction at moderate temperatures, ensuring that foam formation, coating curing, or elastomer synthesis proceeds efficiently and uniformly. 
This catalytic activity is particularly valuable in flexible foams, rigid foams, elastomers, adhesives, and sealants, where precise control over reaction rate, polymer structure, and mechanical properties is critical.

Triethylene diamine is also widely employed as a curing agent for epoxy resins, where it promotes the ring-opening reaction of epoxide groups, resulting in the formation of crosslinked, three-dimensional polymer networks. 
This makes Triethylene diamine crucial in producing adhesives, coatings, composite materials, and electronic encapsulants that require high mechanical strength, chemical resistance, and thermal stability. 
Its ability to catalyze epoxy curing at relatively low temperatures allows manufacturers to achieve efficient processing and improved control over polymer properties.

Due to its strong nucleophilicity and basicity, triethylene diamine is employed as a phase-transfer catalyst in various organic reactions, where it facilitates the migration of reactive ions or molecules from one phase to another. 
This property is widely used in alkylation, acylation, and condensation reactions, enabling efficient conversion of substrates in heterogeneous reaction mixtures. 
Its bicyclic structure provides steric control and selectivity, allowing chemists to favor desired products while minimizing side reactions.

Triethylene diamine serves as a key precursor in the synthesis of quaternary ammonium salts, chelating agents, and organocatalysts. 
These derivatives are widely used in industrial processes, pharmaceuticals, and agrochemical production, as they can act as stabilizers, complexing agents, antimicrobial agents, or polymer additives. 
Triethylene diamine’s high basicity and nucleophilicity make it suitable for constructing functionalized molecules with precisely controlled chemical properties.

In certain industrial applications, triethylene diamine is employed in gas absorption processes, where it reacts selectively with acidic gases such as carbon dioxide, hydrogen sulfide, or sulfur dioxide. 
Its amine functionality allows it to capture and sequester acidic gas molecules efficiently, making it valuable in chemical scrubbing, environmental control, and industrial gas purification systems.

In laboratories, Triethylene diamine is widely used as a base and nucleophilic catalyst for organic synthesis, enabling reactions such as Michael additions, aldol condensations, and epoxide ring-opening reactions. 
Its rigid bicyclic structure provides stereochemical control, making it useful in asymmetric synthesis and mechanistic studies. 
Researchers also employ it in polymerization experiments, organocatalysis development, and advanced material synthesis due to its versatile chemical reactivity and stability.

Triethylene diamine is used in the production of high-performance polymeric materials where its catalytic or structural role contributes to enhanced mechanical, thermal, or chemical properties. 
For example, Triethylene diamine-catalyzed polyurethane or epoxy systems produce foams, coatings, and composites with improved durability, elasticity, and chemical resistance, which are essential for automotive, construction, aerospace, and electronics applications.

Safety Profile:
Triethylene diamine is corrosive to the skin and eyes. 
Direct contact can cause severe irritation, redness, and chemical burns. 
Prolonged exposure or repeated contact may lead to dermatitis or sensitization, making it essential to wear protective gloves, goggles, and clothing when handling the compound. 

Eye exposure can be particularly serious, potentially resulting in conjunctivitis, corneal damage, or temporary vision impairment.
Inhalation of Triethylene diamine dust, aerosols, or vapors can irritate the respiratory tract, causing coughing, shortness of breath, throat irritation, and chest discomfort. 
High-level or prolonged exposure may lead to pulmonary edema, inflammation, or other chronic respiratory conditions. 

Adequate ventilation, fume hoods, and respiratory protection are critical in laboratory or industrial settings.
Accidental ingestion of triethylene diamine can result in gastrointestinal irritation, nausea, vomiting, abdominal pain, and diarrhea. 
Severe ingestion may affect systemic health, potentially leading to toxicity in liver, kidney, or nervous system, although data on chronic ingestion are limited.