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D27802

Sigma-Aldrich

1,4-Diazabicyclo[2.2.2]octane

greener alternative

ReagentPlus®, ≥99%

Synonym(s):

TED, Triethylenediamine

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About This Item

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
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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

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General description

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

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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

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Danger

Hazard Classifications

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

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 1

flash_point_f

144.0 °F - closed cup

flash_point_c

62.2 °C - closed cup

ppe

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

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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)
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)
Multiphoton ionization and two-photon fluorescence excitation spectroscopy of triethylenediamine.
Parker DH and Avouris P.
J. Chem. Phys., 71(3), 1241-1246 (1979)
Proton Magnetic Resonance Studies of Solid Triethylenediamine-Molecular Structure and Motions.
Smith GW.
J. Chem. Phys., 43(12), 4325-4336 (1965)
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