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D27802 Sigma-Aldrich

1,4-Diazabicyclo[2.2.2]octane

Green Alternative

ReagentPlus®, ≥99%

Synonym: TED, Triethylenediamine

  • CAS Number 280-57-9

  • Empirical Formula (Hill Notation) C6H12N2

  • Molecular Weight 112.17

  •  Beilstein/REAXYS Number 103618

  •  EC Number 205-999-9

  •  MDL number MFCD00006689

  •  PubChem Substance ID 57654087

  •  NACRES NA.21

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Properties

Related Categories 12 Principles Aligned Products, Acids & Bases, Bases, Chemical Synthesis, Greener Alternative Products,
Quality Level   200
vapor pressure   2.9 mmHg ( 50 °C)
product line   ReagentPlus®
assay   ≥99%
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, 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.

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.

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

Packaging

2 kg in poly bottle

25, 100, 500 g in poly bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN1325 - class 4.1 - PG 2 - Flammable solids, organic, n.o.s., HI: all
WGK Germany 
WGK 1
RTECS 
HM0354200
Flash Point(F) 
144.0 °F - closed cup
Flash Point(C) 
62.2 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Protocols

Stille Kit

Please consult the Safety Data Sheet for information regarding hazards and safe handling practices.
Keywords: Chromatography, Column chromatography, Gas chromatography, High performance liquid chromatography, Thin layer chromatography

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References

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