D27802

1,4-Diazabicyclo[2.2.2]octane

ReagentPlus^®, ≥99%

• Synonym(s): TED, Triethylenediamine
• Empirical Formula (Hill Notation): C₆H₁₂N₂
• CAS Number: 280-57-9
• Molecular Weight: 112.17
• Beilstein: 103618
• EC Number: 205-999-9
• MDL number: MFCD00006689
• UNSPSC Code: 12352100
• PubChem Substance ID: 57654087
• NACRES: NA.21

Properties

• 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.
• 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

Description

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

Safety Information

• Pictograms: GHS02,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H228 - H302 - H315 - H318
• Precautionary Statements: P210 - P240 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• 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