17473-76-6

Usage

Physical appearance

White to off-white crystalline powder

Solubility

Sparingly soluble in water

Pharmaceuticals

As an intermediate in the synthesis of pharmaceuticals
b. Agrochemicals
c. Dyes

Use in organic synthesis

As a reagent

Potential application

Corrosion inhibitor in cooling water systems

Safety precautions

Handle with appropriate protective equipment, may cause skin and eye irritation

Hazards

Potentially harmful if ingested or inhaled

InChI:InChI=1/C13H11ClN2O/c14-11-6-8-12(9-7-11)15-16-13(17)10-4-2-1-3-5-10/h1-9,15H,(H,16,17)

Upstream product

• 98-88-4 benzoyl chloride 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 64-17-5 ethanol 
• 100-63-0 phenylhydrazine 
• 14572-10-2 benzoyl-(4-chloro-phenyl)-diazene 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 93-97-0 benzoic acid anhydride 
• 17333-85-6 4-chlorophenyldiazonium salt 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 65-85-0 benzoic acid 
• 64-19-7 acetic acid 
• 134-81-6 benzil 

Downstream Products

• 14572-10-2 benzoyl-(4-chloro-phenyl)-diazene 
• 16307-32-7 Bis-<α-(4-chlorphenyl)-β-benzoyl-hydrazino>-methan 
• 1213236-33-9 1-(4-chlorophenyl)-3-methyl-1H-indazole 
• 17359-82-9 N-(α-chlorobenzylidene)-N'-p-chlorophenylhydrazine 
• 63637-57-0 1-(4-chlorophenyl)-3-phenyl-1H-pyrazole 
• 17359-82-9 (Z)-N'-(4-chlorophenyl)benzohydrazonoyl chloride 

Relevant academic research and scientific papers

A [4 + 3] Annulation Reaction of aza- o-Quinone Methides with Arylcarbohydrazonoyl Chlorides for Synthesis of 2,3-Dihydro-1 H-benzo[ e][1,2,4]triazepines

An unprecedented [4 + 3] annulation reaction of aza-ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1H-benzo[e][1,2,4]triazepine.

[3+2]-cycloaddition of in situ generated nitrile imines and acetylene for assembling of 1,3-disubstituted pyrazoles with quantitative deuterium labeling

A novel synthetic methodology for the preparation of 1,3-disubstituted pyrazoles from in situ generated nitrile imines and acetylene is reported. The reactions are performed in a simple two-chamber reactor. One part of the reactor is loaded with hydrazonoyl chloride precursors of active nitrile imine species and a base. The other part is used to generate acetylene from CaC2 and water. Partitioning of the reactants improves the yields of desired pyrazoles up to 99% and simplifies their isolation to a simple procedure of solvent evaporation. The approach requires no complex equipment and utilizes inexpensive, safe, and easy to handle calcium carbide as a starting material. A model deuterium incorporation is carried out according to the developed methodology, producing a series of novel 4,5-dideuteropyrazoles with excellent deuterium enrichment. Theoretical calculations on reaction mechanism and characterization of possible intermediate structures were performed.

Copper(ii)-catalyzed coupling reaction: An efficient and regioselective approach to N′,N′-diaryl acylhydrazines

Using N′-aryl acylhydrazines as aryl donors, a novel copper(ii)-catalyzed homo-coupling reaction of N′-aryl acylhydrazines has been developed for the synthesis of N′,N′-diaryl acylhydrazines. We also provided a complementary procedure for the preparation of unsymmetrical diaryl acylhydrazines via cross-coupling reaction. These protocols featured mild reaction conditions, wide functional group tolerance and highly regioselective products. Control experiments indicated that this kind of coupling reaction might undergo a transient acyl diazene intermediate. This journal is

KOt-Bu promoted homocoupling and decomposition of N'-aryl acylhydrazines: synthesis of unsymmetric N',N'-diaryl acylhydrazines

The KOt-Bu promoted homocoupling and decomposition of N'-aryl acylhydrazines has been achieved. The method allows for a novel and efficient synthesis of unsymmetric N',N'-diaryl acylhydrazines under mild reaction conditions. The reaction probably proceeds via the generation of N'-centered acylhydrazine radicals and the subsequent homolytic aromatic substitution.

Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones

An expeditious multicomponent reaction to synthesize tetrasubstituted furo[2,3-d]pyridazin-4(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo[2,3-d]pyridazin-4(5H)-ones with an unprecedented level of complexity in a triple domino Diels-Alder/retro-Diels-Alder/lactamization reaction sequence.

1,3-Diarylcycloalkanopyrazoles and diphenyl hydrazides as selective inhibitors of cyclooxygenase-2

Novel 1,3-diarylcycloalkanopyrazoles 1, and diphenyl hydrazides 2 were identified as selective inhibitors of cyclooxygenase-2. The 1,3-diaryl substitution pattern of the pyrazole ring in 1 differentiates these compounds from most of the known selective COX-2 inhibitors that contain two aryl rings at the adjacent positions on a heterocyclic or a phenyl ring. Similarly, the two phenyl rings in 2 are also separated by three atoms. SAR of both phenyl rings in 1 and 2, and the aliphatic ring in 1 will be discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

Addition of Semidione Radicals to Arenediazonium Ions: Synthesis of 1,1-Diacyl-2-arylhydrazines

The α-dicarbonyl compounds 1 are selectively reduced to semidione radicals 2 by aqueous Ti3+, via inner-sphere electron transfer (ET).When an equimolar amount of an arenediazonium salt (3) is present, 2 adds to the nitrogen-nitrogen triple bond of 3 to afford the intermediate azo radical cation C, which, depending on the nature of the para substituent of the N-phenyl ring, undergoes rearrangement to a 1,1-diacyl-2-arylhydrazine (4) or preferentially reduction to a hydrazone (5).A mechanism that accounts for both the rearrangement and the substituent effects that are observed is proposed.

Acylation Reactions of Phenylhydrazines. Preparation and Properties of New Diacylphenylhydrazines

Anhydride acylation reactions of a variety of substituted arylhydrazines under mild conditions led to controlled formation of the acid phenylhydrazides I (Table I).The procedures were tallored to the particular state of the starting arylhydrazine.Second-s

Method of use, composition, and compounds

Certain benzoyl chloride phenylhydrazones have been found to be active against insects and mites. The benzoyl ring and the phenylhydrazone ring can be substituted with a halogen atom, a nitro group, or an alkyl group of from 1 to 6 carbon atoms, inclusive