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D27802

1,4-Diazabicyclo[2.2.2]octane

greener alternative

≥99%, crystals, ReagentPlus®

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
NACRES:
NA.21
PubChem Substance ID:
57654087
UNSPSC Code:
12352100
EC Number:
205-999-9
MDL number:
MFCD00006689
Beilstein/REAXYS Number:
103618
Assay:
≥99%
Form:
crystals
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Product Name

1,4-Diazabicyclo[2.2.2]octane, ReagentPlus®, ≥99%

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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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

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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000549983
0000549983
MKCZ3017
0000427511
0000427511

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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)
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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