18523-44-9

Basic information

• Product Name: 1-[4-(dimethylamino)phenyl]triaza-1,2-dien-2-ium
• CAS NO: 18523-44-9
• Molecular Formula: C₈H₁₀N₄
• Molecular Weight: 163.1992
• Mol File: 18523-44-9.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 1-[4-(dimethylamino)phenyl]triaza-1,2-dien-2-ium(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(dimethylamino)phenyl]triaza-1,2-dien-2-ium(18523-44-9)
• EPA Substance Registry System: 1-[4-(dimethylamino)phenyl]triaza-1,2-dien-2-ium(18523-44-9)

Safety Data

• Hazardous Substances Data: 18523-44-9(Hazardous Substances Data)

Usage

General Description

1-[4-(dimethylamino)phenyl]triaza-1,2-dien-2-ium, also known as DABCO, is a chemical compound that belongs to the class of triaza-1,2-dien-2-ium salts. It is commonly used as a catalyst in organic synthesis reactions, especially in the formation of polyurethane foams and in the production of pharmaceuticals and agrochemicals. DABCO is a versatile and widely used compound due to its ability to catalyze a variety of reactions, including Michael additions and ring-opening polymerizations. It is also known for its ability to act as a hydrogen bond acceptor, making it a valuable tool in the design and synthesis of new organic molecules. Additionally, DABCO is used in the production of polymers, dyes, and coatings, further highlighting its importance in the chemical industry.

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 58402-54-3 [p-(N,N-dimethylamino)phenyl]-1H-pentazole 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 75-05-8 acetonitrile 
• 100-04-9 p-dimethylaminobenzenediazonium chloride 
• 28611-39-4 4-(dimethylamino)benzene-boronic acid 
• 536-46-9 4-dimethylaminophenylamine dihydrochloride 
• 171364-78-6 (4-(N,N-dimethylamino)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 30926-05-7 (E)-4,4′-(diazene-1,2-diyl)bis(N,N-dimethylaniline) 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 1009647-36-2 2,6-bis[1-(4-{dimethylamino}phenyl)-1H-1,2,3-triazol-4-yl]-4-(3,6,9-trioxadec-1-yloxy)pyridine 
• 1009647-31-7 2,6-bis[1-(4-{dimethylamino}phenyl)-1H-1,2,3-triazol-4-yl]-4-(3,6,9-trioxadec-1-yloxycarbonyl)pyridine 
• 1452772-93-8 5-(3-methoxy-3-methylbut-1-yn-1-yl)-1,3-bis(4-N,N-dimethylaniline-1H-1,2,3-triazol-4-yl)benzene 
• 1435937-01-1 4-[4-(4,6-dimethylpyrimidin-2-yl)-1H-1,2,3-triazol-1-yl]-N,N-dimethylaniline 
• 42600-58-8 4-(dimethylamino)-1-(chloromethyl)-benzene 
• 57806-78-7 p-dimethylamino-1-(dichloromethyl)benzene 
• 99-97-8 Dimethyl-p-toluidine 
• 34906-70-2 (4-dimethylamino-phenyl)-acetonitrile 

Relevant articles and documents

Detection of pentazolate anion (cyclo-N5-) from laser ionization and decomposition of solid p-dimethylaminophenylpentazole

Laser desorption ionization (LDI) time-of-flight (TOF) mass spectroscopy of solid p-dimethylaminophenylpentazole (1) gives strong peaks of m/z -42 and -70. The -70 peak was identified by 15N labeling of 1 to be the pentazolate anion (cyclo-N5-). The pentazolate anion is formed by an electron attachment to 1 forming the corresponding radical anion followed by a decomposition into 4-N(CH3)2-C 6H4· and (cyclo-N5-). The LDI TOF experimental study also revealed that the (cyclo-N5 -) is very stable. These conclusions are supported by QM calculations at the B3LYP/6-311+G(2df,p) level.

Solution photochemistry of [ p -(Dimethylamino)phenyl]pentazole (DMAPP) at 193 and 300 nm

The photochemistry of [p-(dimethylamino)phenyl]pentazole (DMAPP) at 193 nm and in the near UV is reported, with emphasis on the nature of the final stable products. The (dimethylamino)phenyl azide (DMAPA) is found as a major product in MeCN, but not in dichloromethane (DCM). (In this paper the acronyms DMAPP and DMAPA refer to the para isomers.) The photochemistry of DMAPA is also explored for comparison. The data obtained in MeCN solutions are consistent with the initial formation of the corresponding nitrene, but in DCM, different products are found, on the basis of NMR data. In the case of high reactant concentration in DCM (10-2 M), quantitative conversion of DMAPP and DMAPA is observed, indicating a high quantum yield. In contrast, MeCN solutions react much more slowly. A radical-type chain reaction mechanism is proposed to account for this observation. At high dilution, DMAPP is completely converted to products in both solvents. Possible mechanisms accounting for these results are discussed.

A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including14C and11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.

Catalytic Azoarene Synthesis from Aryl Azides Enabled by a Dinuclear Ni Complex

Azoarenes are valuable chromophores that have been extensively incorporated as photoswitchable elements in molecular machines and biologically active compounds. Here, we report a catalytic nitrene dimerization reaction that provides access to structurally and electronically diverse azoarenes. The reaction utilizes aryl azides as nitrene precursors and generates only gaseous N2 as a byproduct. By circumventing the use of a stoichiometric redox reagent, a broad range of organic functional groups are tolerated, and common byproducts of current methods are avoided. A catalyst featuring a Ni - Ni bond is found to be uniquely effective relative to those containing only a single Ni center. The mechanistic origins of this nuclearity effect are described.