25939-02-0

Basic information

• Product Name: Benzoyl chloride p-fluoro-, phenylhydrazone
• Synonyms: Benzoyl chloride p-fluoro-, phenylhydrazone;1-(α-Chloro-4-fluorobenzylidene)-2-phenylhydrazine;1-[Chloro(4-fluorophenyl)methylene]-2-phenylhydrazine
• CAS NO: 25939-02-0
• Molecular Formula: C₁₃H₁₀ClFN₂
• Molecular Weight: 248.6833032
• Mol File: 25939-02-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 340.38°C at 760 mmHg
• Flash Point: 159.657°C
• Appearance: /
• Density: 1.204g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: Benzoyl chloride p-fluoro-, phenylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoyl chloride p-fluoro-, phenylhydrazone(25939-02-0)
• EPA Substance Registry System: Benzoyl chloride p-fluoro-, phenylhydrazone(25939-02-0)

Safety Data

• Hazardous Substances Data: 25939-02-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H10ClFN2/c14-13(10-6-8-11(15)9-7-10)17-16-12-4-2-1-3-5-12/h1-9,16H/b17-13-

Upstream product

• 108-95-2 phenol 
• 1496-02-2 4-fluoro-N′-phenylbenzohydrazide 
• 352-06-7 1-(4-fluorobenzylidene)-2-phenylhydrazine 
• 459-57-4 4-fluorobenzaldehyde 
• 100-63-0 phenylhydrazine 
• 403-43-0 4-fluorobenzoyl chloride 

Downstream Products

• 128465-19-0 4-Ethylsulfanyl-3-(4-fluoro-phenyl)-1,6-diphenyl-1H-[1,2,4]diazaphosphinine 4-sulfide 
• 128465-11-2 1,4-dihydro-4-thioxo-1,4,6-triphenyl-3-p-fluorophenyl-1,2,4-diazaphosphorine 
• 134241-67-1 4-Ethoxy-5-[1-ethylsulfanyl-meth-(E)-ylidene]-3-(4-fluoro-phenyl)-1-phenyl-1,5-dihydro-[1,2,4]diazaphosphole 4-oxide 
• 92417-39-5 C₃₃H₂₂Br₂FN₂O₂P 
• 1236203-10-3 3-(4-fluoro-phenyl)-1-phenyl-1H-indazole 
• 1228272-94-3 5-(4-chloro-2-fluorophenyl)-3-(4-fluorophenyl)-1-phenyl-1a,6a-dihydropyrrolo[3,4-c]pyrazole-4,6-dione 
• 1314185-32-4 3-(4-fluorophenyl)-1,4-diphenyl-1H-pyrazole-5-carboxylic acid ethyl ester 
• 1251004-71-3 (3aR,6aR,3a'S,6a'S)-5,5'-[methylenebis(4,1-phenylene)]bis[3-(4-fluorophenyl)-3a,6a-dihydro-1-phenylpyrrolo[3,4-c]pyrazole-4,6(1H,5H)-dione] 
• 1354908-59-0 (3aS,6aS)-3-(4-fluorophenyl)-5,6a-dihydro-1-phenyl-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazole-4,6(1H,3aH)dione 
• 1354908-61-4 (3aR,6aR)-3-(4-fluorophenyl)-5,6a-dihydro-1-phenyl-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazole-4,6(1H,3aH)dione 
• 1416008-36-0 tert-butyl 4'-tert-butyl-5'-(4-fluorophenyl)-2-oxo-2'-phenyl-2',4'-dihydrospiro[indoline-3,3'-pyrazole]-1-carboxylate 

Relevant articles and documents

Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs

A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is

Copper-Catalyzed Tandem Dehydrocyanation and [3+2] Cyclo-addition Reactions of Phenacylmalononitriles: Regioselective Synthesis of Functionalized 4-Benzoyl-5-cyanopyrazoles under Mild Conditions

A novel copper-catalyzed [3+2] cycloaddition reaction with concomitant in situ generation of benzoylacrylonitriles and nitrile imines from phenacylmalononitriles and hydrazonoyl chlorides, respectively, is reported. The reaction was performed using copper(I) chloride as catalyst and N-methylimidazole as a clean complexing agent/weak base to afford the functionalized 4-benzoyl-5-cyanopyrazoles in moderate to good yields and excellent regioselectivity under ambient conditions. This method provides rapid access to a wide range of highly functionalized 4-benzoyl-5-cyanopyrazoles.

Transition-Metal-Free Coupling of 1,3-Dipoles and Boronic Acids as a Sustainable Approach to C?C Bond Formation

The need for alternative, complementary approaches to enable C?C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition-metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C?C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis–Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile N-oxides.