39719-02-3

Basic information

• Product Name: Benzoic acid, 4-methyl-, 2-phenylhydrazide
• CAS NO: 39719-02-3
• Molecular Formula: C14H14N2O
• Molecular Weight: 226.278
• Mol File: 39719-02-3.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-methyl-, 2-phenylhydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-methyl-, 2-phenylhydrazide(39719-02-3)
• EPA Substance Registry System: Benzoic acid, 4-methyl-, 2-phenylhydrazide(39719-02-3)

Safety Data

• Hazardous Substances Data: 39719-02-3(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 30410-39-0 3-phenyl-1-(p-tolyl)-2,3-diazaprop-2-en-1-one 
• 874-60-2 4-methyl-benzoyl chloride 
• 100-63-0 phenylhydrazine 
• 2829-32-5 4-Methyl-benzylazo-benzo-α-hydroperoxyd 
• 7732-18-5 water 
• 59-88-1 phenylhydrazine hydrochloride 
• 99-94-5 p-Toluic acid 
• 59046-28-5 p-toluoyl-1H-1,2,3-benzotriazole 
• 36930-95-7 2,2,2-trichloro-1-(4-methylphenyl)ethanone 
• 79071-42-4 2,3-Diphenyl-5-p-tolyl-2,3-dihydro-[1,3,4]oxadiazole 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 26218-73-5 3,4-bis(4-methylphenyl)-1,2,5-oxadiazole-N-oxide 

Downstream Products

• 49829-82-5 4-methyl-N',N'-diphenylbenzohydrazide 
• 3214-05-9 2-phenyl-5-(p-tolyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 33064-20-9 3-(4-methylphenyl)-1-phenyl-1H-pyrazole 
• 25939-01-9 4-methyl-N'-phenylbenzenecarbohydrazonoyl chloride 
• 13756-42-8 tert-butyl 4-methylbenzoate 
• 25939-01-9 p-toluoyl chloride phenylhydrazone 

Relevant articles and documents

Synthesis of 3 H-1,2,4-Triazol-3-ones via NiCl2-Promoted Cascade Annulation of Hydrazonoyl Chlorides and Sodium Cyanate

A nickel-promoted cascade annulation reaction for the facile synthesis of 3H-1,2,4-triazol-3-ones from readily available hydrazonoyl chlorides and sodium cyanate has been developed. The transformation occurs through a cascade nickel-promoted intermolecular nucleophilic addition-elimination process, intramolecular nucleophilic addition, and a hydrogen-transfer sequence. The method has been successfully applied for the construction of the core skeleton of the angiotensin II antagonist.

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.

A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles

N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is

[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.

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.

Synthesis of Spirobidihydropyrazole through Double 1,3-Dipolar Cycloaddition of Nitrilimines with Allenoates

The double 1,3-dipolar cycloaddition of allenoates with nitrilimines has been achieved under mild reaction conditions, affording a variety of spirobidihydropyrazoles in moderate to excellent yields with excellent diastereoselectivities. The reaction diastereoselectively constructs double dihydropyrazole moieties and two chiral centers including a spiro carbon center.

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.

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.

An approach to pyrazoline-fused chlorins by dipolar [3 + 2]-cycloaddition of iminonitriles to Meso-Tetrakis(pentafluorophenyl)porphyrin: Synthesis of new PDT photosensitizers

Meso-Tetrakis(pentafluorophenyl)porphyrin reacts at higher temperature with unstable iminonitriles (RC≡N+-N--Ar), affording pyrazoline-fused chlorins, according to dipolar [3 + 2]-cycloaddition pathway. The respective iminonitriles were in situ generated from the corresponding functionalized α-halogenohydrazine derivatives by 1,3-elimination of HX in the presence of base (NEt3, DABCO). This method allows synthesis of very attractive moieties which may be of potential use as sensitizers in photodynamic therapy (PDT).

Synthesis and antifungal activities of New pyrazole derivatives via 1,3-dipolar cycloaddition reaction

A series of cycloadducts - pyrazoles via 1,3-dipolar cycloaddition reactions of generated nitrilimines with N-(4-chloro-2-fluorophenyl)maleimide were described. The novel compounds synthesized were characterized by 1H NMR, MS, and elemental analysis. The fungicidal tests showed that most of the title compounds exhibit significant fungicidal activities against Corynespora cassiicola.