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D27802

Sigma-Aldrich

1,4-Diazabicyclo[2.2.2]octane

greener alternative

ReagentPlus®, ≥99%

Sinónimos:

TED, Triethylenediamine

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About This Item

Fórmula empírica (notación de Hill):
C6H12N2
Número de CAS:
280-57-9
Peso molecular:
112.17
Beilstein/REAXYS Number:
103618
EC Number:
205-999-9
MDL number:
MFCD00006689
UNSPSC Code:
12352100
PubChem Substance ID:
57654087
NACRES:
NA.21
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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

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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.[1]

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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.[2] It can also be employed as a complexing ligand and as a catalyst.[3] Its gas-phase electronic absorption spectrum,[4] vibrational spectra,[3] multiphoton ionization (MPI), and two-photon fluorescence excitation (TPFE) spectra[5] 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.[6]

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.[2] DABCO may be used in the preparation of the following:[7]
  • 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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Certificados de análisis (COA)

Lot/Batch Number
0000356486
MKCW8172
0000356486
MKCW9000
MKCV8334

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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)
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)
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)
Multiphoton ionization and two-photon fluorescence excitation spectroscopy of triethylenediamine.
Parker DH and Avouris P.
J. Chem. Phys. , 71(3), 1241-1246 (1979)
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Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. What is the storage temperature for the D27802 ? I was used to use the D2522 and it was kept at 4°C.

    1 answer

    1. D27802 is 1,4-Diazabicyclo[2.2.2]octane that can be stored at room temperature but in inert environment. The product should still be suitable to use at 4°C.

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