Skip to Content
MilliporeSigma
All Photos(6)

Documents

D27802

Sigma-Aldrich

1,4-Diazabicyclo[2.2.2]octane

greener alternative

ReagentPlus®, ≥99%

Sign Into View Organizational & Contract Pricing
All Photos(6)
Synonym(s):
TED, Triethylenediamine
Empirical Formula (Hill Notation):
C6H12N2
CAS Number:
280-57-9
Molecular Weight:
112.17
Beilstein/REAXYS Number:
103618
EC Number:
205-999-9
MDL number:
MFCD00006689
UNSPSC Code:
12352100
PubChem Substance ID:
57654087
NACRES:
NA.21

vapor pressure

2.9 mmHg ( 50 °C)

Quality Level

200

product line

ReagentPlus®

assay

≥99%

form

crystals

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

refractive index

n20/D 1.4634 (lit.)

mp

156-159 °C (lit.)

density

1.02 g/mL at 25 °C (lit.)

greener alternative category

, Aligned

SMILES string

N12CCN(CC2)CC1

InChI

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

InChI key

IMNIMPAHZVJRPE-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

1,4-Diazabicyclo[2.2.2]octane (DABCO) is a bicyclic compound used as a strong base and catalyst in organic synthesis.

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.
1,4-Diazabicyclo[2.2.2]octane (DABCO, triethylenediamine), a caged tertiary diamine, is a commonly used strong hindered amine base in chemical synthesis. It can also be employed as a complexing ligand and as a catalyst. Its gas-phase electronic absorption spectrum, vibrational spectra, multiphoton ionization (MPI), and two-photon fluorescence excitation (TPFE) spectra have been recorded and analyzed. Proton magnetic resonance (PMR) studies of DABCO in solid state were conducted in order to determine its line width, second moment, and spin-lattice relaxation time.

Application

1,4-Diazabicyclo[2.2.2]octane (DABCO) may be used in the synthesis of isoxazole derivatives via dehydration of primary nitro compounds in the presence of dipolarophiles. DABCO may be used in the preparation of the following:
  • DABCO bis(perhydrate)
  • DABCO monohydrate
  • DABCO hexahydrate

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Sol. 1 - Skin Irrit. 2

wgk_germany

WGK 1

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Hydrogen bonding in the perhydrate and hydrates of 1,4-diazabicyclo [2.2.2] octane (DABCO).
Laus G, et al.
CrystEngComm, 10(11), 1638-1644 (2008)
Reversible crosslinking and fast stress relaxation in dynamic polymer networks via transalkylation using 1, 4-diazabicyclo [2.2. 2] octane
Maassen EEL, et al.
Open Journal of Polymer Chemistry, 12(25), 3640-3649 (2025)
Structure and Intramolecular Motions in Triethylenediamine as Studied by Gas Electron Diffraction.
Yokozeki A and Kuchitsu K.
Bulletin of the Chemical Society of Japan, 44(1), 72-77 (1971)
Experimental vibrational spectra and computational study of 1,4-diazabicyclo [2.2.2] octane.
Kovalenko VI, et al.
Journal of Molecular Structure, 1028, 134-140 (2012)
1,4-Diazabicyclo [2.2.2] octane (DABCO) as an Efficient Reagent for the Synthesis of Isoxazole Derivatives from Primary Nitro Compounds and Dipolarophiles: The Role of the Base.
Cecchi L, et al.
European Journal of Organic Chemistry, 2006(21), 4852-4860 (2006)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service