155742-57-7

Basic information

• Product Name: 1H-Imidazole-2-carboxaldehyde, 1-[(4-methylphenyl)sulfonyl]-
• CAS NO: 155742-57-7
• Molecular Formula: C11H10N2O3S
• Molecular Weight: 250.278
• Mol File: 155742-57-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-2-carboxaldehyde, 1-[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-2-carboxaldehyde, 1-[(4-methylphenyl)sulfonyl]-(155742-57-7)
• EPA Substance Registry System: 1H-Imidazole-2-carboxaldehyde, 1-[(4-methylphenyl)sulfonyl]-(155742-57-7)

Safety Data

• Hazardous Substances Data: 155742-57-7(Hazardous Substances Data)

Usage

Molecular structure

Consists of an imidazole ring with a carboxaldehyde group and a sulfonyl group attached to the 1-position of the imidazole ring.

Physical form

Pale yellow solid.

Uses

Commonly used as a reagent in organic synthesis, specifically for the synthesis of various N-sulfonyl imidazoles, which are important intermediates in the pharmaceutical and agrochemical industries. Also used as a reagent in the preparation of other organic compounds and as a catalyst in various chemical reactions.

Versatility

1H-Imidazole-2-carboxaldehyde, 1-[(4-methylphenyl)sulfonyl]is a versatile compound with wide applications in the field of organic synthesis.

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 10111-08-7 2-imidazolecarbaldehyde 

Downstream Products

• 155742-59-9 ((N-p-Toluenesulfonyl)imidazol-2-yl)methyl methanesulfonate 
• 875553-56-3 1-(1-tosyl-1H-imidazol-2-yl)ethan-1-one 
• 1027263-71-3 C₃₀H₃₁N₇O₆S₂ 
• 191982-65-7 (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-2-(phenylmethyl)-3-{[1-(tolylsulfonyl)imidazol-2-yl]methyl}cyclopent[4,5]imidazo[2,1-b]purin-4(3H)-one 
• 191982-64-6 2-bromomethyl-1-(toluene-4-sulfonyl)-1H-imidazole 
• 191982-49-7 C₂₉H₂₉N₇O₄S 
• 155742-58-8 [1-(toluene-4-sulfonyl)-1H-imidazol-2-yl]-methanol 

Relevant articles and documents

Functionalization of the Imidazole Backbone by Means of a Tailored and Optimized Oxidative Heck Cross-Coupling

A general and selective Pd-catalyzed cross-coupling of aromatic boronic acids with vinyl-imidazoles is disclosed. Unlike most cross-coupling reactions, this method operates well in absence of bases avoiding the formation of by-products. The reactivity is highly enhanced by the presence of nitrogen-based ligands, in particular bathocuproine. The method involves MnO2 as oxidant for the oxidation Pd (0)→Pd (II), a much weaker oxidant than previously reported in the literature. This allows for the use of reactants that possess a multitude of functional groups. A scope and limitation study involving a series of 24 boronic acids, whereof 18 afforded TMs in yields in the range 41–95%. The disclosed method constitutes the first general method for the oxidative Heck cross-coupling on the imidazole scaffold, which moreover operates with a selection of other heterocycles. (Figure presented.).

IMIDAZOLE-BASED ANTICANCER AGENTS AND DERIVATIVES THEREOF, AND METHODS OF MAKING AND USING SAME

Imidazole-based anticancer agents and derivatives thereof, as well as methods of making and methods of using the same, are described. The imidazole-based anticancer agents are HDAC inhibitor compounds having a 1-(1H-imidazol-2-yl)ethan-1-one or 1-(1H-imidazol-2-yl)ethane-1- thione moiety.

Potent tetracyclic guanine inhibitors of PDE1 and PDE5 cyclic guanosine monophosphate phosphodiesterases with oral antihypertensive activity

Tetracyclic guanines have been shown to be potent and selective inhibitors of the cGMP-hydrolyzing enzymes PDE1 and PDE5. In general, these compounds are inactive or only weakly active as inhibitors of PDE3, which is a major isozyme involved in cAMP hydrolysis. Structureactivity relationships are developed at N-l, C-2, N-3, and N-5 on the core nucleus. Compound 31, with an IC50 of 70 pM, is the most potent inhibitor of PDE1, while 50, with an IC50 of 4 nM, is the most potent inhibitor of PDE5. Compounds 20, 22, 30, and 50 are potent dual inhibitors with IC50 values below 30 nM for both PDE1 and PDE5. Compounds 12, 20, and 28 reduced blood pressure by more than 45 mmHg when administered orally at 10 mg/kg to the spontaneously hypertensive rat (SHR).