17263-64-8

Usage

Uses

Used in Organic Synthesis:
(Z)-2-diazonio-1-(4-methylphenyl)ethenolate is used as a reagent for introducing the azo group into organic compounds. This application is due to its high reactivity, which allows for the formation of new chemical bonds and the creation of a wide range of azo-containing compounds.
Used in Azo Dye Preparation:
In the dye industry, (Z)-2-diazonio-1-(4-methylphenyl)ethenolate is used as a key intermediate for the preparation of azo dyes. Its role in this application is to provide the necessary azo group, which is a common structural element in many dyes, imparting vibrant colors to fabrics and other materials.
Used in Carbon-Carbon and Carbon-Heteroatom Bond Formations:
(Z)-2-diazonio-1-(4-methylphenyl)ethenolate is also utilized in the formation of carbon-carbon and carbon-heteroatom bonds, which are essential in constructing complex organic molecules and frameworks. Its reactivity facilitates the creation of these bonds, making it a valuable tool in organic chemistry.
Safety Note:
Due to the sensitivity and explosive nature of (Z)-2-diazonio-1-(4-methylphenyl)ethenolate, it should be handled with extreme caution and appropriate safety measures should be taken to prevent accidents and ensure the safety of those working with (Z)-2-diazonio-1-(4-methylphenyl)ethenolate.

InChI:InChI=1/C9H8N2O/c1-7-2-4-8(5-3-7)9(12)6-11-10/h2-6H,1H3/b9-6-

Upstream product

• 186581-53-3 diazomethane 
• 874-60-2 4-methyl-benzoyl chloride 
• 53073-02-2 sodium salt of p-toluoylacetaldehyde 
• 14377-02-7 3-oxo-3-p-tolyl-propionaldehyde 
• 99-94-5 p-Toluic acid 
• 122-00-9 para-methylacetophenone 
• 16208-14-3 2,2-dihydroxy-1-(p-tolyl)ethanone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 619-41-0 4-(bromoacetyl)toluene 
• 3594-36-3 1,3-bis(p-methylphenyl)-1,3-propanedione 
• 277298-59-6 C₉H₉ClN₂O 
• 105141-03-5 2-diazo-1,3-bis(4-methylphenyl)propane-1,3-dione 

Downstream Products

• 55577-25-8 2-(4-methylphenyl)-1H-indole 
• 64837-47-4 (5-chloro-[1,2,3]thiadiazol-4-yl)-p-tolyl-methanone 
• 64837-48-5 (5-chloro-[1,3,4]thiadiazol-2-yl)-p-tolyl-methanone 
• 64591-47-5 2-methoxy-1-(4-methylphenyl)ethan-1-one 
• 14869-40-0 α-ethoxy-p-methylacetophenone 
• 75608-70-7 α-chloro-α-phenylselenomethyl p-tolyl ketone 
• 68395-78-8 2-methyl-5-(4-methylphenyl)-1,3-oxazole 
• 77901-28-1 1-p-Tolyl-2-(2,4,6-trimethoxy-phenyl)-ethanone 
• 77901-38-3 N-[(Z)-2-p-Tolyl-2-(2,4,6-trimethoxy-phenyl)-vinyl]-acetamide 
• 77901-33-8 N-[(E)-2-p-Tolyl-2-(2,4,6-trimethoxy-phenyl)-vinyl]-acetamide 
• 104023-09-8 α-bromo-α-phenylselenomethyl p-tolyl ketone 
• 104023-11-2 α-acetoxy-α-phenylselenomethyl p-tolyl ketone 
• 123725-18-8 2-Diazo-1-(4-methylphenyl)-2-(pentamethyldisilanyl)-ethanone 
• 36734-50-6 1‐(4‐methylphenyl)‐2‐(phenylsulfanyl)ethanone 

Relevant academic research and scientific papers

First example of the coupling of α-diazoketones with thiourea: a novel route for the synthesis of 2-aminothiazoles

α-Diazoketones undergo smooth coupling with thiourea in the presence of 10 mol % of copper(II) triflate to produce the corresponding 2-aminothiazoles in excellent yields with high selectivity. The use of copper(II) triflate makes this method simple, convenient and practical. This method works well with both aryl and alkyl diazoketones to furnish a wide range of 2-aminothiazoles.

An efficient PEG-400 mediated catalyst free green synthesis of 2-amino-thiazoles from α-diazoketones and thiourea

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles from α-diazoketones using PEG-400 solvent system. This novel synthetic approach involves the reaction between thiourea and α-diazoketones in PEG-400 at 100 °C to yield the corresponding 2-aminothiazoles in good yields. The method is simple, rapid and generates thiazole derivatives in excellent yields without the use of any catalysts. This green protocol can be utilized for fast synthesis of various 2-aminothiazoles in good yields. [Figure not available: see fulltext.]

One-pot synthesis of polyfunctional pyrazoles: An easy access to α-diazoketones from arylglyoxal monohydrates and tosylhydrazine

A new and efficient method for the generation of α-diazoketones has been developed from arylglyoxal monohydrates and tosylhydrazine at room temperature. 1,3-Dipolar cycloaddition reactions were used to constructing polyfunctional pyrazole derivatives by the reaction of generated α-diazoketones in situ with electron-deficient alkenes, quinones and coumarins in one pot. The one-dimensional molecular packing of 1H-benzo[f]indazole-4,9-dione derivatives along the c direction demonstrated a helical chain formation via N-H?O hydrogen-bonding.

Phosphoric Acid Catalyzed [4 + 1]-Cycloannulation Reaction of ortho-Quinone Methides and Diazoketones: Catalytic, Enantioselective Access toward cis-2,3-Dihydrobenzofurans

A highly straightforward route to enantiomerically highly enriched cis-2,3-dihydrobenzofurans has been achieved via addition of α-diazocarbonyl compounds to in situ generated o-QMs catalyzed by a chiral Br?nsted acid. This catalytic strategy provides a direct access to 2,3-dihydrobenzofurans in high yields and with up to 91:9 dr and 99:1 er at ambient temperature. Moreover, a unique phenonium-type rearrangement accounts for product formation with an inverted 2,3-substitution pattern.

Rhodium-mediated 18F-oxyfluorination of diazoketones using a fluorine-18-containing hypervalent iodine reagent

Geminal 18F-oxyfluorination of diazoketones was performed in the presence of rhodium mediators. The reactions were performed using a hypervalent iodine-based [18F]fluoro-benziodoxole reagent. By this methodology various α-[18/s

Tandem Synthesis of α-Diazoketones from 1,3-Diketones

A highly efficient synthesis of α-diazoketone was achieved by simply stirring the mixture of 1,3-diketone, TsN3, and MeNH2 in EtOH. It was a tandem reaction including a novel primary amine-catalyzed Regitz diazo transfer of 1,3-diket

Safe and reliable synthesis of diazoketones and quinoxalines in a continuous flow reactor

A flow method for the synthesis of aliphatic and aromatic diazoketones from acyl chloride precursors has been developed and used to prepare quinoxalines in a multistep sequence without isolation of the potentially explosive diazoketone. The protocol showcases an efficient in-line purification using supported scavengers with time-saving and safety benefits and in particular a reduction in the operator's exposure to carcinogenic phenylenediamines.

A cascade approach to pyridines from 2-Azido-2,4-dienoates and α-diazocarbonyl compounds

A one-pot synthesis of substituted pyridines via a cascade reaction of 2-azido-2,4-dienoates with α-diazocarbonyl compounds and triphenylphosphine is reported. The process involves a Staudinger-Meyer reaction, a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring- closure. The procedure is general and efficient. The substrates are readily available.

Indium triflate: A mild and efficient Lewis acid catalyst for O-H insertion reactions of α-diazo ketones

Facile O-H insertion reactions of α-diazo ketones with aliphatic/aromatic alcohols or benzenethiol have been developed in the presence of indium triflate as a catalyst. These reactions provided good yields of α-alkoxy ketones. A comparative study with other Lewis acids establishes the reactivity of indium triflate in O-H insertion reactions of α-diazo ketones.

N-isocyanotriphenyliminophosphorane; a convenient reagent for the conversion of acyl chlorides into α-diazoketones

Aliphatic, aromatic and vinylic acid chlorides were converted into the corresponding α-diazoketones in synthetically useful yields by reaction with N-isocyanotriphenyliminophosphorane followed by treatment of the resulting N- unsubstituted α-ketohydrazido