Triethylenediamine Chemical Properties

Melting point:

156-159 °C(lit.)

Boiling point:

174 °C

Density 

1.02 g/mL

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 

400g/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℃

CAS DataBase Reference

280-57-9(CAS DataBase Reference)

NIST Chemistry Reference

Triethylenediamine(280-57-9)

EPA Substance Registry System

1,4-Diazabicyclo[2.2.2]octane (280-57-9)

Safety Information

Hazard Codes 

Xn,F

Risk 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

Autoignition Temperature

350 °C

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29335920

Hazardous Substances Data

280-57-9(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 700 mg/kg

MSDS

• Language:English Provider:1,4-Diazabicyclo[2.2.2]octane
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Triethylenediamine Usage And Synthesis

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

An anti-fade reagent shown to scavenge free-radicals due to flurochrome excitation.

Uses

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.]

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