280-57-9

Basic information

• Product Name: Triethylenediamine
• Synonyms: 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;bicyclo(2.2.2)-1,4-diazaoctane;Bicyclo[2.2.2]-1,4-diazaoctane
• CAS NO: 280-57-9
• Molecular Formula: C₆H₁₂N₂
• Molecular Weight: 112.17
• EINECS: 205-999-9
• Product Categories: pharmacetical;Polyamines;API intermediates;Biochemistry;Reagents for Oligosaccharide Synthesis
• Mol File: 280-57-9.mol
• Article Data: 60

Chemical Properties

• Melting Point: 156-159 °C(lit.)
• Boiling Point: 174 °C
• Flash Point: 198 °F
• Appearance: White to pale yellow/Hygroscopic Crystals
• Density: 1.02 g/mL
• Vapor Pressure: 2.9 mm Hg ( 50 °C)
• Refractive Index: n20/D 1.4634(lit.)
• Storage Temp.: 2-8°C
• Solubility: 400g/l
• PKA: 3.0, 8.7(at 25℃)
• Water Solubility: 46 g/100 mL (26 ºC)
• Sensitive: Hygroscopic
• Stability: Stable, but very hygroscopic. Incompatible with strong oxidizing agents, strong acids. Highly flammable.
• Merck: 14,9669
• BRN: 103618
• CAS DataBase Reference: Triethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: Triethylenediamine(280-57-9)
• EPA Substance Registry System: Triethylenediamine(280-57-9)

Safety Data

• Hazard Codes: Xn,F
• Statements: 22-36/37/38-52/53-41-36/38-11
• Safety Statements: 26-60-37/39-3-16-36/37-61
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 1
• RTECS: HM0354200
• F: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 280-57-9(Hazardous Substances Data)

Usage

Chemical Properties

Triethylenediamine 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.

Uses

Different sources of media describe the Uses of 280-57-9 differently. You can refer to the following data:
1. An anti-fade reagent shown to scavenge free-radicals due to flurochrome excitation.
2. 1,4-Diazabicyclo[2.2.2]octane is used as polyurethane catalyst, Balis-Hillman reaction catalyst complexing ligand and lewis base. It 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. Further, it is an oxidation and polymerization catalyst.

Definition

ChEBI: Triethylenediamine is an organic heterobicylic compound that is piperazine with an ethane-1,2-diyl group forming a bridge between N1 and N4. It is typically used as a catalyst in polymerization reactions. It has a role as a catalyst, a reagent and an antioxidant. It is a bridged compound, a tertiary amino compound, a saturated organic heterobicyclic parent and a diamine.

Preparation

Triethylenediamine can be produced from ethylenediamine or ethanolamine, diethanolamine, or diethylenetriamine with a variety of different catalysts.

Reactions

Triethylenediamine 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, triethylenediamine exhibits catalytic activity in base-catalyzed reactions.

General Description

Dabco?33-LV (Db) is a gelling catalyst and a bidentate ligand that forms a self-assembled monolayer (SAM) on a variety of substrates. It functionalizes the surface and immobilizes the surface atoms.

Hazard

Skin irritant.

Flammability and Explosibility

Flammable

Purification Methods

DABCO crystallises from 95% EtOH, pet ether or MeOH/diethyl ether (1:1). Dry it under vacuum over CaCl2 and BaO. It can be sublimed in vacuo, and readily at room temperature. It has also been purified by removal of water during azeotropic distillation of a *benzene solution. It is then recrystallised twice from anhydrous diethyl ether under argon, and stored under argon [Blackstock et al. J Org Chem 52 1451 1987]. [Beilstein 23/3 V 487.]

InChI:InChI=1/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2

Synthetic route

C6H8N2O2 → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With Rh/Al2O3; hydrogen In tetrahydrofuran at 175℃; under 37503.8 Torr; Reagent/catalyst; Temperature; Solvent; Sealed tube;	87.6%

1-(2-hydroxyethyl)piperazine (103-76-4) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With aluminum phosphate molded body In water at 380℃;	76%
With silica gel In water at 380℃; for 10h; Reagent/catalyst; Gas phase;	75%
With aluminum oxide; silica gel
at 300℃; Leiten des Dampfes ueber einen SiO2/Al2O3-Katalysator;

aminoethylpiperazine (140-31-8) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With H type zeolite(ZSM-5) In water at 380℃;	75%
With water; Na-type ZSM-5(3) at 355 - 370℃;	46.3%

1,4-diamino-1,4-diazonia-bicyclo[2.2.2]octane; dibromide (115050-43-6) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In water at 18 - 20℃; under 1.5 - 1.8 Torr;	74%

1-(2-hydroxyethyl)piperazine (103-76-4) → piperazine (110-85-0) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With water; Na-type ZSM-5(2) at 340℃;	A 4.1% B 68.1%

sodium methylate (124-41-4) + 1-[2-(2,4,6-Tri-tert-butyl-phenylphosphanylidene)-ethyl]-4-aza-1-azonia-bicyclo[2.2.2]octane; bromide (126995-92-4) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + C21H35OP (126995-93-5)

Conditions	Yield
In methanol at 60℃; for 1h;	A n/a B 65%
In methanol at 60℃; for 1h; Yield given;

ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) → piperazine (110-85-0) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With ZSM-5 type zeolite In water at 370℃; pH=10; Temperature; pH-value;	A 63% B 17%
With ZSM-5 type zeolite In water at 330℃; pH=10; Temperature; pH-value;	A 44% B 56%
With ZSM-5 type zeolite with Na exchange rate of 62percent In water at 290℃; Reagent/catalyst; Temperature;
With Na-ion exchanged ZSM-5 type zeolite In water at 290 - 600℃; Gas phase;
With β-type iron silicate at 320℃; Reagent/catalyst;

aminoethylpiperazine (140-31-8) + ethylenediamine (107-15-3) → piperazine (110-85-0) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With ZSM-5 type zeolite In water at 320℃; pH=9; Temperature; pH-value;	A 54% B 46%

aminoethylpiperazine (140-31-8) → piperazine (110-85-0) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With ZSM-5 type zeolite In water at 350℃;	A 26% B 53%
With water; Na-type ZSM-5(2) at 350 - 370℃;	A 20.2% B 47.7%
Na-type ZSM-5(6) at 355 - 380℃;	A 18.9% B 39.9%

triethylentetramine (112-24-3) → piperazine (110-85-0) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With water; Na-type ZSM-5(2) at 360 - 370℃;	A 14.8% B 43.7%

N,N'-bisethylenediamine (113682-68-1) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
at 350℃;	30%

methanol (67-56-1) + ethanolamine (141-43-5) → ethyleneimine (151-56-4) + piperazine (110-85-0) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + (2-hydroxyethyl)(methyl)amine (109-83-1)

Conditions	Yield
With Cs-P-Si mixed-oxide at 300℃; under 750.06 Torr; Title compound not separated from byproducts;	A 37 % Chromat. B n/a C n/a D 6%

methanol (67-56-1) + ethanolamine (141-43-5) → piperazine (110-85-0) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + (2-hydroxyethyl)(methyl)amine (109-83-1)

Conditions	Yield
With H-β-zeolite at 250℃; under 750.06 Torr; Title compound not separated from byproducts;	A n/a B n/a C 2%

Chloroethylpiperazine (61308-25-6) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With diethyl ether

1,4-bis(2-hydroxyethyl)piperazine (122-96-3) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With aluminum oxide; silica gel
at 325℃; under 19 Torr; Leiten des Dampfes ueber einen Siliciumdioxid-Aluminiumoxid-Katalysator;

diethanolamine hydrochloride (14426-21-2) → morpholine (110-91-8) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
at 220℃;

1-(2-bromo-ethyl)-piperazine; dihydrobromide (89727-93-5) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
at 240℃;

1-(2-chloroethyl)-piperazine dihydrochloride (53502-60-6, 54267-47-9, 75256-75-6) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
at 240℃;

N,N'-bis(2-bromoethyl)piperazine dihydrobromide (90942-23-7) → piperazine (110-85-0) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
at 275℃;

1,4-dimethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium dibromide (5450-74-8) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
at 230 - 240℃; under 0.003 Torr;
at 230 - 240℃; under 0.003 Torr; Pyrolysis;
at 260℃; under 0.001 Torr; Pyrolysis;

1,4-dimethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium dibromide (5450-74-8) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1H,4H-piperazine-N,N’-diium dibromide (59813-05-7)

Conditions	Yield
at 350℃; under 0.002 Torr; Pyrolysis;

triethanolamine hydrochloride (637-39-8) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With ammonium chloride at 230℃;

tris-(2-chloroethyl)amine hydrochloride (817-09-4) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With ammonium chloride at 270℃;

1,5-diamino-3-azapentane (111-40-0) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9)

Conditions	Yield
With kaolin at 390℃;

aminoethylpiperazine (140-31-8) + formaldehyd (50-00-0) + formic acid (64-18-6) + 1,2-dichloro-ethane (107-06-2) → N,N'-dimethylpiperazine (106-58-1) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + 1-<2-(diethylamino)ethyl>-4-methylpiperazine + N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

Conditions	Yield
Mechanism;

...Expand

aminoethylpiperazine (140-31-8) + formaldehyd (50-00-0) + formic acid (64-18-6) + 1,2-dichloro-ethane (107-06-2) → N,N'-dimethylpiperazine (106-58-1) + 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-<2-(diethylamino)ethyl>-4-methylpiperazine + N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

Conditions	Yield
With 2.) alkali 1.) alcohol; Multistep reaction. Further byproducts given;

aminoethylpiperazine (140-31-8) + formaldehyd (50-00-0) + formic acid (64-18-6) + 1,2-dichloro-ethane (107-06-2) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + 1-<2-(diethylamino)ethyl>-4-methylpiperazine + N,N'-dimethyl-N,N'-bis<2-(4-methyl-1-piperazinyl)ethyl>ethylenediamine

Conditions	Yield
Multistep reaction. Further byproducts given;

1-Phenethyl-4-aza-1-azonia-bicyclo[2.2.2]octane (73997-41-8) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + styrene (292638-84-7)

Conditions	Yield
With potassium hydroxide; potassium chloride In water at 40℃; Mechanism; Rate constant; further base-solvent system;

1-[2-(4-Nitro-phenyl)-ethyl]-4-aza-1-azonia-bicyclo[2.2.2]octane (73997-39-4) → 1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 4-nitrostyrene (100-13-0)

Conditions	Yield
With potassium hydroxide; potassium chloride In water at 25℃; Mechanism; Rate constant; Equilibrium constant; further bases;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + p-nitrobenzene iodide (636-98-6) → 1-(4-Nitro-phenyl)-4-aza-1-azonia-bicyclo[2.2.2]octane; iodide (112473-28-6)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 75h;	100%
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h; Yield given;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + ethyldiiodophosphine (13868-72-9) → C14H29N4P(2+)*2I(1-)

Conditions	Yield
In dichloromethane for 6h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 4-chlorobenzonitrile (100-00-5) → 1-(4-Nitro-phenyl)-4-aza-1-azonia-bicyclo[2.2.2]octane; chloride (112473-26-4)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 75h;	100%
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h; Yield given;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + para-nitrophenyl bromide (586-78-7) → 1-(4-Nitro-phenyl)-4-aza-1-azonia-bicyclo[2.2.2]octane; bromide (112473-27-5)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 75h;	100%
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h; Yield given;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 4-aza-1-p-nitrobenzylazoniabicyclo<2.2.2>octane bromide (136497-64-8)

Conditions	Yield
In diethyl ether for 20h;	100%
In diethyl ether	97%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + trifluorormethanesulfonic acid (1493-13-6) → N,N'-difluoro-1,4-diazoniabicyclo<2.2.2>octane bis(triflate)

Conditions	Yield
With fluorine In various solvent(s)	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + ethyl 2-(acetoxy(phenyl)methyl)acrylate (105479-98-9) → Acetate1-((E)-2-ethoxycarbonyl-3-phenyl-allyl)-4-aza-1-azonia-bicyclo[2.2.2]octane;

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 0.25h;	100%
In tetrahydrofuran; water at 20℃; for 0.166667h;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 3-acetoxy-2-methylene-3-phenylpropionitrile (138597-12-3, 144299-84-3, 144370-28-5, 143165-00-8) → Acetate1-((E)-2-cyano-3-phenyl-allyl)-4-aza-1-azonia-bicyclo[2.2.2]octane;

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 0.25h;	100%
In tetrahydrofuran; water at 20℃; for 0.166667h;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + ethyl 2-(acetoxy(2,4-dichlorophenyl)methyl)acrylate → Acetate1-[(E)-3-(2,4-dichloro-phenyl)-2-ethoxycarbonyl-allyl]-4-aza-1-azonia-bicyclo[2.2.2]octane;

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 0.25h;	100%
In tetrahydrofuran; water at 20℃; for 0.166667h;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + ethyl 2-(acetoxy (p-tolyl)methyl)acrylate → 1-(2-ethoxycarbonyl-3-p-tolyl-allyl)-4-aza-1-azonia-bicyclo[2.2.2]octane; acetate

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 0.25h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + acetic acid 2-cyano-1-(3-methoxy-phenyl)-allyl ester → Acetate1-[(E)-2-cyano-3-(3-methoxy-phenyl)-allyl]-4-aza-1-azonia-bicyclo[2.2.2]octane;

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 0.25h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + ethyl 2-(acetoxy(3-methoxyphenyl)methyl)acrylate → Acetate1-[(E)-2-ethoxycarbonyl-3-(3-methoxy-phenyl)-allyl]-4-aza-1-azonia-bicyclo[2.2.2]octane;

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 0.25h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-bromo-octane (111-83-1) → 1‐octyl‐1,4‐diazabicyclo[2.2.2]octan‐1‐ium bromide

Conditions	Yield
In dichloromethane for 12h; Reflux;	100%
In tetrahydrofuran at 60℃; for 24h;	95%
In ethyl acetate at 20℃; for 24h;	91%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 4-trifluoromethylbenzyl chloride (939-99-1) → 1-(4-(trifluoromethyl)benzyl)-4-aza-1-azonia-bicyclo[2.2.2]octane chloride

Conditions	Yield
In tetrahydrofuran for 2h; Heating;	100%
In tetrahydrofuran at 20℃; for 12h;	92%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + methyl 2,6-dichloronicotinate (65515-28-8) → 1-(6-chloro-5-methoxycarbonyl-pyridin-2-yl)-4-aza-1-azonia-bicyclo[2.2.2]octane

Conditions	Yield
In tetrahydrofuran at 5 - 20℃; for 16.5h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 2-amino 2-methyl 3-((tetrahydro 2H-pyran 2-yl) oxy) propanenitrile + benzenesulfonyl chloride (98-09-9) → N-[1-cyano-1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-C-benzylsulfonamide

Conditions	Yield
In tetrahydrofuran at 20℃; for 15h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 2-(5-hydroxyindane-2-yl)isoindole-1,3-dione (685832-34-2) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → dimethylthiocarbamic acid O-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)indan-5-yl] ester (685832-35-3)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 18h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + Methyl 2-Hydroxy-4-[({[3-hydroxy-4-(methoxycarbonyl)-phenyl]methyl}amino)methyl]benzoate Hydrochloride (311343-83-6) + di-tert-butyl dicarbonate (24424-99-5) → Methyl 4-[((tert-butoxy)-N-{[3-hydroxy-4-(methoxycarbonyl)-phenyl]methyl}carbonylamino)methyl]-2-hydroxybenzoate

Conditions	Yield
In methanol; hexane; ethyl acetate	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + naphthalene-1,4-dicarboxylic acid (605-70-9) + copper (12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8) → Cu(II)(1,4-naphthalenedicarboxylate)(DABCO)0.5

Conditions	Yield
With N-methyl-N,N,N-tributylammonium methyl sulfate In methanol at 39℃; for 2h; Electrochemical reaction;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1,3-dibromo-propane (109-64-8) → 1,1''-(propane-1,3-diyl)bis(1,4-diazabicyclo[2.2.2]-octan-1-ium)dibromide (97497-67-1)

Conditions	Yield
In methanol at 20℃; for 24h;	100%
In methanol at 20℃; for 20h;	97%
In acetonitrile at 20℃; for 24h;	74%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 2,3,4,5,6-pentafluorobenzyl iodide → 1-pentafluoro benzylammonium-4-aza-1-azonia bicyclo[2.2.2]octane iodide (1229616-94-7)

Conditions	Yield
In chloroform at 20℃; for 24h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 2,3,4,5,6-pentafluorobenzyl chloride (653-35-0) → C13H14F5N2(1+)*Cl(1-) (1229616-83-4)

Conditions	Yield
In chloroform at 20℃; for 24h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) → 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate (119752-83-9)

Conditions	Yield
With sulfur dioxide	100%
With sulfuric acid; sodium carbonate In tetrahydrofuran at 20℃;	99%
With sulfur dioxide at -78℃; Inert atmosphere; Reflux;	98%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1,3-propanesultone (1120-71-4) → N,N'-bis(3-sulfopropyl)triethylenediaminium bis(hydrogensulfate)

Conditions	Yield
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; 1,3-propanesultone In tetrahydrofuran for 24h; Reflux; Stage #2: With sulfuric acid at 170℃; for 20h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + [(5,15-diphenylporphinato(-H))zinc(II)(CC)iron(II)(η5-C5Me5)(1,2-bis(diphenylphosphino)ethane)]*0.3CH2Cl2 → [(5,15-diphenylporphinato(-H))zinc(II)(pyridine)(CC)iron(II)(η5-C5Me5)(1,2-bis(diphenylphosphino)ethane)] dichloromethane disolvate

Conditions	Yield
In dichloromethane at 20℃; for 3h; Inert atmosphere; Schlenk technique;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-acetyl-N-phenylcyclopropane-1-carboxamide (937733-22-7) → C18H25N3O2

Conditions	Yield
In acetonitrile at 60℃;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + C48H28N4O4Zn + ethylenediamine (107-15-3) → C110H84N18Zn2

Conditions	Yield
In chloroform at 20℃; for 24h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + C48H28N4O4Zn + Trimethylenediamine (109-76-2) → C114H92N18Zn2

Conditions	Yield
In chloroform at 20℃; for 24h;	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + C9H9N3O2S2*C4H10N2 → C9H9N3O2S2*C6H12N2

Conditions	Yield
In ethanol	100%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + C47H21B3F18O6 → C112H78B6F36N6O12

Conditions	Yield
In chloroform at 20℃;	100%

Upstream product

• 61308-25-6 Chloroethylpiperazine 
• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 122-96-3 1,4-bis(2-hydroxyethyl)piperazine 
• 14426-21-2 diethanolamine hydrochloride 
• 89727-93-5 1-(2-bromo-ethyl)-piperazine; dihydrobromide 
• 53502-60-6 1-(2-chloroethyl)-piperazine dihydrochloride 
• 90942-23-7 N,N'-bis(2-bromoethyl)piperazine dihydrobromide 
• 5450-74-8 1,4-dimethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium dibromide 
• 637-39-8 triethanolamine hydrochloride 
• 817-09-4 tris-(2-chloroethyl)amine hydrochloride 
• 111-40-0 3-azapentane-1,5-diamine 
• 107-15-3 ethylenediamine 
• 141-43-5 ethanolamine 
• 111-42-2 2,2'-iminobis[ethanol] 

Downstream Products

• 5450-74-8 1,4-dimethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium dibromide 
• 42790-43-2 N,N'-dibenzyl-1,4-diazonia bicyclo[2.2.2]octane dichloride 
• 14870-72-5 1,4-dimethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium diiodide 
• 93-97-0 benzoic acid anhydride 
• 18503-52-1 1,4-Diazabicyclo<2.2.2>octane N-oxide 
• 60420-20-4 1-methyl-4-aza-1-azonia-bicyclo[2.2.2]octane; chloride-hydrochloride 
• 81539-93-7 1-Methyl-4-(2-hydroxyethyl)piperazine Benzoate 
• 81539-95-9 Benzoic acid 2-(4-methyl-piperazin-1-yl)-ethyl ester; hydrobromide 
• 81539-88-0 Benzoate₁-methyl-4-aza-1-azonia-bicyclo[2.2.2]octane; 
• 112473-28-6 1-(4-Nitro-phenyl)-4-aza-1-azonia-bicyclo[2.2.2]octane; iodide 
• 122323-92-6 2-(1,4-diazabicyclo<2.2.2>octyl)diphenylcarbinol 
• 108-94-1 cyclohexanone 
• 280-57-9 1,4-diazabicyclo<2.2.2>octane radical cation 
• 4255-62-3 4,4-dimethylcyclohexane-1-one 

Relevant articles and documents

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Generation of a Mn(IV)-Peroxo or Mn(III)-Oxo-Mn(III) Species upon Oxygenation of Mono- and Binuclear Thiolate-Ligated Mn(II) Complexes

A thiolate-bridged binuclear complex [PPN]2[(MnII(TMSPS3))2] (1, PPN = bis(triphenylphosphine)iminium and TMSPS3H3 = (2,2′,2″-trimercapto-3,3′,3″-tris(trimethylsilyl)triphenylphosphine)), prepared from the reaction of MnCl2/[PPN]Cl and Li3[TMSPS3], converts into a mononuclear complex [PPN][MnII(TMSPS3)(DABCO)] (2) in the presence of excess amounts of DABCO (DABCO = 1,4-diazabicyclo[2.2.2]octane). Variable temperature studies of solution containing 1 and DABCO by UV-vis spectroscopy indicate that 1 and 2 exist in significant amounts in equilibrium and mononuclear 2 is favored at low temperature. Treatment of 1 or 2 with the monomeric O2-side-on-bound [PPN][MnIV(O2)(TMSPS3)] (3) produces the mono-oxo-bridged dimer [PPN]2[(MnIII(TMSPS3))2(μ-O)] (4). The electrochemistry of 1 and 2 reveals anodic peak(s) for a MnIII/MnII redox couple at shifted potentials against Fc/Fc+, indicating that both complexes can be oxidized by dioxygen. The O2 activation mediated by 1 and 2 is investigated in both solution and the solid state. Microcrystals of 2 rapidly react with air or dry O2 to generate the Mn(IV)-peroxo 3 in high yield, revealing a solid-to-solid transformation and two-electron reduction of O2. Oxygenation of 1 or 2 in solution, however, is affected by diffusion and transient concentration of dioxygen in the two different substrates, leading to generation of 3 and 4 in variable ratios.

Degradation of Organic Cations under Alkaline Conditions

Understanding the degradation mechanisms of organic cations under basic conditions is extremely important for the development of durable alkaline energy conversion devices. Cations are key functional groups in alkaline anion exchange membranes (AAEMs), and AAEMs are critical components to conduct hydroxide anions in alkaline fuel cells. Previously, we have established a standard protocol to evaluate cation alkaline stability within KOH/CD3OH solution at 80 °C. Herein, we are using the protocol to compare 26 model compounds, including benzylammonium, tetraalkylammonium, spirocyclicammonium, imidazolium, benzimidazolium, triazolium, pyridinium, guanidinium, and phosphonium cations. The goal is not only to evaluate their degradation rate, but also to identify their degradation pathways and lead to the advancement of cations with improved alkaline stabilities.

METHOD FOR PRODUCING PIPERAZINE AND TRIETHYLENEDIAMINE

PROBLEM TO BE SOLVED: To provide a method for producing piperazine and triethylenediamine in combination, making it possible to provide piperazine with high selectivity and high yields. SOLUTION: Under a basic condition with pH of 8 or more, pentasil type zeolite subjected to ion exchange with alkali metal salt, and one or more amine react with each other, under a condition of 50 wt.% or more substrate concentration. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Hetero Face-to-Face Porphyrin Array with Cooperative Effects of Coordination and Host–Guest Complexation

We successfully synthesized a hetero face-to-face porphyrin array composed of ZnTPP and RuTPP(DABCO)2 (TPP: 5, 10, 15, 20-tetraphenylporphyrin, DABCO: 1,4-diazabi-cyclo[2.2.2]octane) in 2:1 molar ratio. A cyclic Zn porphyrin dimer (ZnCP) was also used as the host molecule for the Ru porphyrin. In the latter, the Ru-DABCO bonding in RuTPP(DABCO)2 was stabilized by the host-guest complexation. Reaction progress kinetic analysis of the ligand substitution reaction of RuTPP(DABCO)2 and that in ZnCP revealed the stabilization mechanism of the Ru-DABCO bonding. Photoinduced electron transfer (PET) from the Zn porphyrin to the Ru porphyrin was observed in the porphyrin array. The host-guest stabilization of unstable complex for construction of a donor—acceptor–donor structure is expected to be a new method for an artificial photosynthesis.