68654-23-9

Basic information

• Product Name: 2,3,6,7-Tetramethyl-1,5-diazabicyclo[3.3.0]octa-2,6-diene-4,8-dione
• Synonyms: 2,3,6,7-Tetramethyl-1,5-diazabicyclo[3.3.0]octa-2,6-diene-4,8-dione;anti-(Methyl,methyl)bimane
• CAS NO: 68654-23-9
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21448
• Mol File: 68654-23-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,6,7-Tetramethyl-1,5-diazabicyclo[3.3.0]octa-2,6-diene-4,8-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6,7-Tetramethyl-1,5-diazabicyclo[3.3.0]octa-2,6-diene-4,8-dione(68654-23-9)
• EPA Substance Registry System: 2,3,6,7-Tetramethyl-1,5-diazabicyclo[3.3.0]octa-2,6-diene-4,8-dione(68654-23-9)

Safety Data

• Hazardous Substances Data: 68654-23-9(Hazardous Substances Data)

Usage

General Description

2,3,6,7-Tetramethyl-1,5-diazabicyclo[3.3.0]octa-2,6-diene-4,8-dione, also known as DABCO, is a chemical compound with the molecular formula C10H16N2O2. It is a stable, crystalline, and highly soluble compound that is commonly used as a catalyst in organic synthesis reactions. DABCO is a bicyclic amine that is widely employed in the pharmaceutical and polymer industries for the synthesis of various drugs, plastics, and resins. It is also used as a curing agent and stabilizer in the production of epoxy resins. In addition, DABCO has been studied for its potential application in medicine as an antifungal and antibacterial agent due to its unique chemical structure and properties.

Upstream product

• 82666-00-0 (Z)-3-(3,4-Dimethyl-5-oxo-2,5-dihydro-pyrazol-1-yl)-2-methyl-but-2-enoic acid 
• 6628-22-4 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 68654-22-8 9,10-dioxa-syn-(methyl,methyl)bimane 
• 79746-44-4 α,β-dimethyl-β-<3,4-dimethyl-5-hydroxypyrazol-1-yl>acrylic acid lactone 
• 100130-07-2 4-bromo-3,4-dimethylpyrazol-5-one 
• 68654-32-0 3,4-dimethyl-4-chloro-2-pyrazolin-5-one 
• 33549-66-5 4,4-dibromo-5-methyl-2,4-dihydro-3H-pyrazol-3-one 

Downstream Products

• 74235-78-2 9,10-dioxa-anti-(bromomethyl,methyl)(methyl,methyl)bimane 

Relevant articles and documents

The Synthesis and Chemistry of Azolenines. Part 5. Correction of the structure of an Unusual Heterocycle, Described on Two Earlier Occasions as the Pyrano-4H-pyrazole: 3,3a,4,5-Tetramethylpyranopyrazol-6(3aH)-one

A compound, prepared previously by two different methods, and clamed to be the title compound (2), is shown to be the isomer 3,4,7,8-tetramethyl-1,5-diazabicycloocta-3,7-diene-2,6-dione (11a), a known oxopyrazolopyrazolone.Other products from the same and related reactions are also identified and characterised.

Bimanes. 10. Photochemical Rearrangement of 1,5-Diazabicycloocta-3,7-diene-2,6-diones (9,10-Dioxa-anti-bimanes)

1,5-Diazabicycloocta-3,7-diene-2,6-diones (9,10-dioxa-anti-bimanes) rearrange quantitatively on irradiation in the 320 nm absorption band to isomeric lactones, one from symmetrical bimanes and two from unsymmetrical bimanes ("mixed" bimanes).The quantum yield of lactone is often high and depends upon bimane substitution and solvent viscosity.Fast intersystem crossing (Huppert et al.), oxygen inhibition of lactone formation, and efficient formation of lactone via a triplet sensitizer implicate the triplet as a key intermediate.The suggested mechanism of lactoneformation involves a twisted ?-?* triplet.