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Basic Information
CAS No.: 280-57-9
Name: Triethylenediamine
Article Data: 81
Molecular Structure:
Molecular Structure of 280-57-9 (Triethylenediamine)
Formula: C6H12N2
Molecular Weight: 112.175
Synonyms: Thancat TD 33A;Toral SM 2;Toyocat L 33;Toyocat TEDA L 33;Triethylenediamine;1,4-Ethylenepiperazine;33LV;A 33;AE 33;Activator 105E;Bicyclo[2.2.2]-1,4-diazaoctane;D 33LV;DABCO Crystal;Dabco;Dabco 33LV;Dabco 3LV;Dabco Crystalline;Dabco L 1202;Dabco S 25;Jeffcat TD 100;Kaolizer 31;L 33;L 33E;LC 96003;LV 33;Minico L1020;N,N'-endo-Ethylenepiperazine;NSC 56362;Niax A 33;PC CAT TD 33;PC-TD;Polycat 33LV;TD 100;TED;TEDA;Teda L 33;Tegamine 33;Tego Amine;Tegoamin33;Texacat TD 100;Texacat TD 33;Thancat TD 33;
EINECS: 205-999-9
Density: 1.08 g/cm3
Melting Point: 156-159 °C(lit.)
Boiling Point: 174 °C at 760 mmHg
Flash Point: 62.2 °C
Solubility: 46 g/100 mL (26 °C) in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn, FlammableF
Risk Codes: 22-36/37/38-52/53-41-36/38-11
Safety: 26-60-37/39-3-16-36/37
Transport Information: UN 1325 4.1/PG 2
PSA: 6.48000
LogP: -0.50660
Synthetic route

C6H8N2O2

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
With Rh/Al2O3; hydrogen In tetrahydrofuran at 175℃; under 37503.8 Torr; Reagent/catalyst; Temperature; Solvent; Sealed tube;87.6%
103-76-4

1-(2-hydroxyethyl)piperazine

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
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;
140-31-8

aminoethylpiperazine

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
With H type zeolite(ZSM-5) In water at 380℃;75%
With water; Na-type ZSM-5(3) at 355 - 370℃;46.3%
115050-43-6

1,4-diamino-1,4-diazonia-bicyclo[2.2.2]octane; dibromide

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In water at 18 - 20℃; under 1.5 - 1.8 Torr;74%
103-76-4

1-(2-hydroxyethyl)piperazine

A

110-85-0

piperazine

B

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
With water; Na-type ZSM-5(2) at 340℃;A 4.1%
B 68.1%
124-41-4

sodium methylate

126995-92-4

1-[2-(2,4,6-Tri-tert-butyl-phenylphosphanylidene)-ethyl]-4-aza-1-azonia-bicyclo[2.2.2]octane; bromide

A

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

B

126995-93-5

C21H35OP

Conditions
ConditionsYield
In methanol at 60℃; for 1h;A n/a
B 65%
In methanol at 60℃; for 1h; Yield given;
107-15-3

ethylenediamine

111-40-0

1,5-diamino-3-azapentane

A

110-85-0

piperazine

B

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
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;
140-31-8

aminoethylpiperazine

107-15-3

ethylenediamine

A

110-85-0

piperazine

B

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
With ZSM-5 type zeolite In water at 320℃; pH=9; Temperature; pH-value;A 54%
B 46%
140-31-8

aminoethylpiperazine

A

110-85-0

piperazine

B

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

Conditions
ConditionsYield
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%
112-24-3

triethylentetramine

A

110-85-0

piperazine

B

280-57-9

1,4-diaza-bicyclo[2.2.2]octane

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

Molecular structure of 1,4-Diazabicyclo(2.2.2)octane (CAS NO.280-57-9) is:

Product Name: 1,4-Diazabicyclo(2.2.2)octane
CAS Registry Number: 280-57-9
IUPAC Name: 1,4-diazabicyclo[2.2.2]octane 
Molecular Weight: 112.17288 [g/mol]
Molecular Formula: C6H12N2
XLogP3-AA: -0.2
H-Bond Donor: 0
H-Bond Acceptor: 2 
EINECS: 205-999-9
Melting Point: 156-159 °C(lit.)
Refractive index: n20/D 1.4634(lit.)
Storage temp.: 2-8°C
Water Solubility: 46 g/100 mL (26 ºC)
Sensitive: Hygroscopic 
Surface Tension: 42.3 dyne/cm
Density: 1.08 g/cm3
Flash Point: 62.2 °C
Enthalpy of Vaporization: 41.03 kJ/mol
Boiling Point: 174 °C at 760 mmHg
Vapour Pressure: 1.23 mmHg at 25°C
Stability: Stable, but very hygroscopic. Incompatible with strong oxidizing agents, strong acids. Highly flammable.
Product Categories: pharmacetical;Polyamines;API intermediates;Biochemistry;Reagents for Oligosaccharide Synthesis

Uses

 1,4-Diazabicyclo(2.2.2)octane (CAS NO.280-57-9) is used as a catalyst, particularly in making polyurethanes, and complexing ligand.Also it is a useful catalyst in the Baylis-Hillman reaction.And it can be used to adjust pH of the oxygen-sensitive resin to regulate the reaction rate in Flexplay time-limited DVDs. It has also been used as a catalyst for a metal-free Sonogashira coupling, with or without microwave enhancement.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 2250mg/kg (2250mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(5), Pg. 67, 1980.
rabbit LD50 oral 1100mg/kg (1100mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(5), Pg. 67, 1980.
rat LD50 oral 1700mg/kg (1700mg/kg)   Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 393, 1974.
 

Safety Profile

Moderately toxic by ingestion. A skin and eye irritant, allergen, and skin sensitizer. A powerful base. Forms an explosive complex with hydrogen peroxide. Mixtures with carbon auto-ignite at 230°C. Very exothermic reaction with cellulose nitrate. When heated to decomposition it emits toxic fumes of NOx. See also AMINES
Hazard Codes: HarmfulXn,FlammableF
Risk Statements: 22-36/37/38-52/53-41-36/38-11 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R41:Risk of serious damage to the eyes. 
R36/38:Irritating to eyes and skin. 
R11:Highly flammable.
Safety Statements: 26-60-37/39-3-16-36/37 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S60:This material and its container must be disposed of as hazardous waste. 
S37/39:Wear suitable gloves and eye/face protection. 
S3:Keep in a cool place. 
S16:Keep away from sources of ignition. 
S36/37:Wear suitable protective clothing and gloves.
RIDADR: UN 1325 4.1/PG 2
WGK Germany: 1
RTECS: HM0354200
F: 3
HazardClass: 8
PackingGroup: III
HS Code: 29335920

Specification

 1,4-Diazabicyclo(2.2.2)octane , its cas register number is 280-57-9. It also can be called 1,4-Diazabicyclo[2.2.2]octane ; Dabco ; Quinuclidine ; Triethylenediamine ; N,N'-endo-Ethylenepiperazine .It is a white crystalline powder.It smells like peanuts.