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D27802

Sigma-Aldrich

1,4-Diazabicyclo[2.2.2]octane

greener alternative

ReagentPlus®, ≥99%

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Synonym(s):
TED, Triethylenediamine
Empirical Formula (Hill Notation):
C6H12N2
CAS Number:
Molecular Weight:
112.17
Beilstein:
103618
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

vapor pressure

2.9 mmHg ( 50 °C)

Quality Level

product line

ReagentPlus®

Assay

≥99%

form

crystals

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

refractive index

n20/D 1.4634 (lit.)

mp

156-159 °C (lit.)

density

1.02 g/mL at 25 °C (lit.)

greener alternative category

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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1 of 4

This Item
1390098.03456682101
form

crystals

form

liquid

form

solid

form

-

refractive index

n20/D 1.4634 (lit.)

refractive index

n20/D 1.522-1.524 (lit.)

refractive index

-

refractive index

-

mp

156-159 °C (lit.)

mp

-

mp

155-158 °C

mp

>250 °C

density

1.02 g/mL at 25 °C (lit.)

density

1.018 g/mL at 25 °C (lit.)

density

1.14 g/cm3 at 25 °C

density

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 1

Flash Point(F)

144.0 °F - closed cup

Flash Point(C)

62.2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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)
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)
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)

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