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D27802 Sigma-Aldrich

1,4-Diazabicyclo[2.2.2]octane

ReagentPlus®, ≥99%

Synonym: TED, Triethylenediamine

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Properties

Related Categories Acids & Bases, Bases, Chemical Synthesis, Organic Bases, Synthetic Reagents More...
grade   ReagentPlus®
vapor pressure   2.9 mmHg ( 50 °C)
assay   ≥99%
refractive index   n20/D 1.4634(lit.)
mp   156-159 °C(lit.)
density   1.02 g/mL at 25 °C(lit.)

Description

General description

Strong hindered amine base.

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

Price and Availability

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1,4-<WBR>Diazabicyclo[2.2.2]<WBR>octane hydrochloride, polymer-bound

100-200 mesh, extent of labeling: ~2.0 mmol/g N loading, 1 % cross-linked with divinylbenzene

Quinuclidine

97%

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1325 4.1 / PGII
WGK Germany 
1
RTECS 
HM0354200
Flash Point(F) 
143.6 °F
Flash Point(C) 
62 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

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Peer-Reviewed Papers

References

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The cell adhesion molecule L1 regulates the expression of choline acetyltransferase and the development of septal cholinergic neurons. Xuezhi Cui et al Brain Behav. 1, 73-86, (2011)

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Inhibition of mRNA export and dimerization of interferon regulatory factor 3 by Theiler's virus leader protein. Ricour C J. Gen. Virol. 90(Pt 1), 177-86, (2009)

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A systematic study of transfection efficiency and cytotoxicity in HeLa cells using iron oxide nanoparticles prepared with organic and inorganic bases. Calmon MF, de Souza AT, Candido NM, et al. Colloids Surf. B Biointerfaces 100, 177-84, (2012)

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[Mechanism of cytotoxicity of artificial ribonucleases in various human cancer cell lines]. Logashenko EB, Kuznetsova IL, Riabchikova EI, et al. Biomed. Khim. 56(2), 230-43, (2010)

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Templated synthesis of a large and flexible covalent porphyrinic cage bearing orthogonal recognition sites. Taesch J, Heitz V, Topić F, et al. Chem. Commun. (Camb.) 48(42), 5118-20, (2012)

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DABCO-Bis(sulfur dioxide), DABSO, as a Convenient Source of Sulfur Dioxide for Organic Synthesis: Utility in Sulfonamide and Sulfamide Preparation Woolven, H., et al. Org. Lett. 13, 4876-4878, (2011)

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Photochemical activation of TRPA1 channels in neurons and animals. Kokel D, Cheung CY, Mills R, et al. Nat. Chem. Biol. 9(4), 257-63, (2013)

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CuCl/DABCO/4-HO-TEMPO-catalyzed aerobic oxidative synthesis of 2-substituted quinazolines and 4H-3,1-benzoxazines. Han B, Yang XL, Wang C, et al. J. Org. Chem. 77(2), 1136-42, (2012)

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PRIMA-1MET induces nucleolar translocation of Epstein-Barr virus-encoded EBNA-5 protein. György Stuber et al Mol. Cancer 8, 23, (2009)

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Molecular and cellular analysis of B-cell populations in the rainbow trout using Pax5 and immunoglobulin markers. Zwollo P Dev. Comp. Immunol. 32(12), 1482-96, (2008)

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Size-dependent catalysis by DABCO-functionalized Zn-MOF with one-dimensional channels. Gu JM, Kim WS, and Huh S Dalton Trans. 40(41), 10826-9, (2011)

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Diffusion controlled hydrogen atom abstraction from tertiary amines by the benzyloxyl radical. The importance of C-H/N hydrogen bonding. Salamone M, Anastasi G, Bietti M, et al. Org. Lett. 13(2), 260-3, (2011)

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Kinetic resolution of secondary alcohols by the combination of a chiral Brønsted acid, DABCO, and acetyl chloride. Mandai H, Murota K, Mitsudo K, et al. Org. Lett. 14(13), 3486-9, (2012)

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Highly asymmetric bromocyclization of tryptophol: unexpected accelerating effect of DABCO-derived bromine complex. Liu H, Jiang G, Pan X, et al. Org. Lett. 16(7), 1908-11, (2014)

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Acute toxicity and biodegradability of N-alkyl-N-methylmorpholinium and N-alkyl-DABCO based ionic liquids. Pretti C, Renzi M, Focardi SE, et al. Ecotoxicol. Environ. Saf. 74(4), 748-53, (2011)

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From attraction to repulsion: anion-π interactions between bromide and fluorinated phenyl groups. Giese M, Albrecht M, Bannwarth C, et al. Chem. Commun. (Camb.) 47(30), 8542-4, (2011)

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DABCO-catalyzed regioselective cyclization reactions of β,γ-unsaturated α-ketophosphonates or β,γ-unsaturated α-ketoesters with allenic esters. Pei CK, Wu L, Lian Z, et al. Org. Biomol. Chem. 10(1), 171-80, (2012)

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Adiponectin-coated nanoparticles for enhanced imaging of atherosclerotic plaques. Almer G Int. J. Nanomedicine 6, 1279-90, (2011)

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Novel self-assembling system based on resorcinarene and cationic surfactant. Kashapov RR, Pashirova TN, Kharlamov SV, et al. Phys. Chem. Chem. Phys. 13(35), 15891-8, (2011)

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C. elegans ATAD-3 is essential for mitochondrial activity and development. Hoffmann M PLoS ONE 4(10), e7644, (2009)

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DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate. Wang Y, Yu ZH, Zheng HF, et al. Org. Biomol. Chem. 10(38), 7739-46, (2012)

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Silver/ThioClickFerrophos complex as an effective catalyst for asymmetric conjugate addition of glycine imino ester to unsaturated malonates and α-enones. Konno T, Watanabe S, Takahashi T, et al. Org. Lett. 15(17), 4418-21, (2013)

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Synthesis of 2-alkoxy(aroxy)-3-substituted quinolines by DABCO-promoted cyclization of o-alkynylaryl isocyanides. Zhao J, Peng C, Liu L, et al. J. Org. Chem. 75(21), 7502-4, (2010)

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Characterization of enhanced-fluidity liquid hydrophilic interaction chromatography for the separation of nucleosides and nucleotides. Philibert GS and Olesik SV J. Chromatogr. A 1218(45), 8222-30, (2011)

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Conjugated-polyelectrolyte-grafted cotton fibers act as "micro flypaper" for the removal and destruction of bacteria. Ista LK, Dascier D, Ji E, et al. ACS Appl. Mater. Interfaces 3(8), 2932-7, (2011)

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Premature chromosome condensation induced by caffeine, 2-aminopurine, staurosporine and sodium metavanadate in S-phase arrested HeLa cells is associated with a decrease in Chk1 phosphorylation, formation of phospho-H2AX and minor cytoskeletal rearrangements. Rybaczek D Histochem. Cell Biol. 135(3), 263-80, (2011)

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An indolocarbazole-bridged macrocyclic porphyrin dimer having homotropic allosterism with inhibitory control. Lee CH, Yoon H, Kim P, et al. Chem. Commun. (Camb.) 47(14), 4246-8, (2011)

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Multifunctional bioconjugation by Morita-Baylis-Hillman reaction in aqueous medium. Li GL, Kung KK, Zou L, et al. Chem. Commun. (Camb.) 48(29), 3527-9, (2012)

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Derivatization of peptides as quaternary ammonium salts for sensitive detection by ESI-MS. Cydzik M, Rudowska M, Stefanowicz P, et al. J. Pept. Sci. 17(6), 445-53, (2011)

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Cyclization cascades initiated by 1,6-conjugate addition. Brooks JL and Frontier AJ J. Am. Chem. Soc. 134(40), 16551-3, (2012)

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Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines. Andrews IP, Blank BR, and Kwon O Chem. Commun. (Camb.) 48(43), 5373-5, (2012)

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Screening for toxic amyloid in yeast exemplifies the role of alternative pathway responsible for cytotoxicity. Julien Couthouis et al PLoS ONE 4, e4539, (2009)

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Mutational analysis of the herpes simplex virus type 1 DNA packaging protein UL33. Frauke Beilstein et al J. Virol. 83, 8938-45, (2009)

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Wnt signaling activates Shh signaling in early postnatal intervertebral discs, and re-activates Shh signaling in old discs in the mouse. Winkler T, Mahoney EJ, Sinner D, et al. PLoS ONE 9(6), e98444, (2014)

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Ring-opening reactions of 1,4-diazabicyclo[2.2.2]octane (DABCO) derived quaternary ammonium salts with phenols and related nucleophiles. Maraš N, Polanc S, and Kočevar M Org. Biomol. Chem. 10(6), 1300-10, (2012)

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Luminescence spectroscopic observation of singlet oxygen formation in extra virgin olive oil as affected by irradiation light wavelengths, 1,4-diazabicyclo[2.2.2]octane, irradiation time, and oxygen bubbling. Jung MY, Choi DS, Park KH, et al. J. Food Sci. 76(1), C59-63, (2011)

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Insoluble, speckled cytosolic distribution of retinoic acid receptor alpha protein as a marker of hepatic stellate cell activation in vitro. Mezaki Y J. Histochem. Cytochem. 57(7), 687-99, (2009)

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Photoisomerization of alfa calcidol by a sensitized quantum chain reaction. Estruch GA and Aramendía PF Photochem. Photobiol. 88(4), 769-73, (2012)

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Merck 14,9669

Beil. 23,V,3,487

Fieser 1,1203 / Fieser 2,99 / Fieser 4,119 / Fieser 5,176 / Fieser 6,157 / Fieser 7,86 / Fieser 11,153 / Fieser 12,155 / Fieser 13,92 / Fieser 15,109

Aldrich MSDS 1, 571:D / Corp MSDS 1 (1), 1005:A / Corp MSDS 1 (1), 1061:D / FT-IR 2 (1), 592:D / FT-IR 1 (1), 380:D / FT-NMR 1 (1), 595:A / IR-Spectra (3), 225:C / IR-Spectra (2), 201:G / NMR-Reference 2 (1), 334:C / RegBook 1 (1), 399:O / RegBook 1 (1), 399:N / Sax 6, 895 / Sigma FT-IR 1 (2), 435:B / Structure Index 1, 57:C:8 / Vapor Phase 3, 471:C

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