1,4-diazabicyclo[2.2.2]octane

• ChemBase ID: 104899
• Molecular Formular: C6H12N2
• Molecular Mass: 112.17288
• Monoisotopic Mass: 112.10004839
• SMILES: C1CN2CCN1CC2
• Canonical SMILES: C1CN2CCN1CC2
• InChI: InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2
• InChIKey: IMNIMPAHZVJRPE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-diazabicyclo[2.2.2]octane
• IUPAC Traditional name: dabco
• Synonyms: 1,4-Diazabicyclo[2.2.2]octane solution; Dabco® 33-LV; triethylenediamine, TEDA; DABCO; 1,4-Diazabicyclo[2.2.2]octane; TEDA; DABCO; Triethylenediamine; 1,4-DIAZABICYCLO-[2.2.2]OCTANE; 1,4-DIAZABICYCLO-(2,2,2)-OCTANE; 1,4-DIAZABICYCLO-(2.2.2)OCTANE; TED; 1,4-Diazabicyclo[2.2.2]octane; 1,4-二叠氮双环[2.2.2]辛烷 溶液; 1,4-二氮双环[2.2.2]辛烷; 三乙烯二胺; 1,4-二叠氮双环[2.2.2]辛烷; More...

Database IDs

• CAS Number: 280-57-9
• EC Number: 205-999-9
• MDL Number: MFCD00006689
• Beilstein Number: 103618
• Merck Index: 149669
• PubChem SID: 162093073; 24857483; 24893714
• PubChem CID: 9237
• Chemspider ID: 8882
• Wikipedia Title: DABCO

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -3.7987516
• LogD (pH = 7.4): -2.8268335
• Log P: -0.1342359
• Molar Refractivity: 34.0692 cm^3
• Polarizability: 13.381781 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble, hygroscopic in water
• Apperance: White crystalline powder
• Melting Point: 155-160°C; 156 - 160 °C; 156-159 °C; 156-159 °C(lit.); 158 °C (316 °F); 158°C
• Boiling Point: 174 °C (345 °F); 174 °C; 174°C; 174-176°C
• Flash Point: >110 °C; >230 °F; 143.6 °F; 62 °C; 62.22°C; 62°C(143°F)
• Density: 1.02 g/mL; 1.02 g/mL at 25 °C(lit.); 1.14 at 28 °C (water = 1); 1.140
• Refractive Index: n20/D 1.4634(lit.)
• Vapor Pressure: 0.45 mm Hg at 20 °C; 2.9 mmHg ( 50 °C)
• Vapor Density: 3.86 (air = 1)

Safety Information

• Storage Condition: 2-8°C, Desiccate, Store Under Nitrogen
• Storage Warning: Hygroscopic
• RTECS: HM0354200
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 1325; UN1325
• German water hazard class: 1
• Hazard Class: 3; 4.1
• Packing Group: 2; III
• Risk Statements: 11-22-36/37/38-52/53; 11-22-37/38-41; 22-36/37/38-52/53; R:10-22-36/37/38; R:22-36/37/38; R11 R22 R36 R37 R38 R52 R53
• Safety Statements: 26-36/37/39-60; 26-60; 26-61; S:16-26-46-36/37/39; S:25-26-36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger; Warning
• Main Hazard: Harmful
• GHS Hazard statements: H228-H302-H315-H319-H335-H412; H315-H319-H335-H412; H318-H315-H228-H302-H335
• GHS Precautionary statements: P210-P241-P305+P351+P338-P302+P352-P405-P501A; P210-P261-P273-P305 + P351 + P338; P261-P273-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1325 4.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (NT); ≥99%; 98%
• Grade: purum; ReagentPlus®
• Description: 33 wt. % solution of triethylenediamine in dipropylene glycol
• Empirical Formula (Hill Notation): C6H12N2

DETAILS

MP Biomedicals - 05205945

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157609

(DABCO: Triethylenediamine)
Purified

MP Biomedicals - 02195137

Crystalline

Sigma Aldrich - D2522

Application
清除由荧光物激发产生的自由基的抗淬灭剂。在荧光显微术中添加到封固剂中以延缓荧光素和其他荧光染料的光漂白。

Sigma Aldrich - 290734

Packaging
100, 500 mL in poly bottle
Legal Information
DABCO is a registered trademark of Air Products & Chemicals, Inc.

Sigma Aldrich - D27802

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

REFERENCES

• Promotes the cleavage of ?-keto esters in refluxing xylene directly to ketones, without the need for prior hydrolysis: J. Org. Chem., 39, 1592, 2647 (1974). Similarly, malonic esters can be cleaved to esters of substituted acetic acids: J. Org. Chem., 41, 208 (1976).
• In conjunction with palladium acetate and PEG-400 provides a reusable catalyst system for the Suzuki-Miyaura cross-coupling reaction of boronic acids: J. Org. Chem., 70, 5409 (2005).
• Dabco is a registered trademark of Air Products and Chemicals Inc.
• Forms crystalline complexes with organolithium compounds: J. Am. Chem. Soc., 87, 3276 (1965), which show enhanced reactivity, e.g. in the high yield ɑ-metallation of thioanisole by n-BuLi: J. Org. Chem., 31, 4097 (1966).
• Forms a stable crystalline complex with H₂O₂, useful as an equivalent to "anhydrous" H₂O₂: reaction with TMS chloride gives bis(TMS) peroxide, a useful OH⁺-equivalent, e.g. in the conversion of aryllithiums to phenols: Synthesis, 633 (1986).
• Catalyzes the addition of aldehydes to Michael acceptors at the ɑ-position (Baylis-Hillman reaction): Helv. Chim. Acta, 63, 413 (1984):
  
• For further illustrative example, see: Org. Synth., 75, 106 (1997). Complete reaction often takes several days at ambient temperature, while heating causes lower yields. However, it is greatly accelerated by microwave irradiation: Synlett, 444 (1994). Superior results with reduced reaction times can be achieved in aqueous medium: J. Org. Chem., 66, 5413 (2001). The use as reaction medium of tetramethylene sulfone: Tetrahedron Lett., 45, 1183 (2004), or PEG-400: Tetrahedron Lett., 45, 5865 (2004) has also been advocated. Lithium perchlorate was found to increase the reaction rate dramatically: Tetrahedron Lett., 40, 1539 (1999), as was a catalytic amount of a metal triflate, particularly La or Sm; conventional Lewis acids were ineffective: J. Org Chem., 63, 7183 (1998). For asymmetric Baylis-Hillman reaction using (1S,2R)-(-)-10,2-Camphorsultam, A15897, as chiral auxiliary, see: J. Am. Chem. Soc., 119. 4317 (1997). See also 3-Quinuclidinol, B21503. For more recent discussion and comparison of different catalysts, see: J. Org. Chem., 692 (2003). In a reinterpretaion of the mechanism, a hemiacetal interemediate has been proposed: J. Org. Chem., 70, 3980 (2005). For reviews of the Baylis-Hillman reaction, see: Tetrahedron, 44, 4653 (1988); 52, 8001 (1996).