26165-67-3

Basic information

• Product Name: 4-(2,5-DIMETHYL-1H-PYRROL-1-YL)BENZOHYDRAZIDE
• Synonyms: 4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzohydrazide, 1-[4-(Hydrazinocarbonyl)phenyl]-2,5-dimethyl-1H-pyrrole;4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzhydrazide;4-(2,5-DIMETHYL-1H-PYRROL-1-YL)BENZOHYDRAZIDE;4-[1-(2,5-DIMETHYLPYRROLO)]BENZOHYDRAZIDE;4-(2,5-Dimethyl-pyrrol-1-yl)-benzoic acid hydrazide;4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzoic acid hydrazide
• CAS NO: 26165-67-3
• Molecular Formula: C₁₃H₁₅N₃O
• Molecular Weight: 229.28
• Mol File: 26165-67-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 168 °C
• Appearance: /
• Density: 1.18 g/cm³
• Refractive Index: 1.609
• CAS DataBase Reference: 4-(2,5-DIMETHYL-1H-PYRROL-1-YL)BENZOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,5-DIMETHYL-1H-PYRROL-1-YL)BENZOHYDRAZIDE(26165-67-3)
• EPA Substance Registry System: 4-(2,5-DIMETHYL-1H-PYRROL-1-YL)BENZOHYDRAZIDE(26165-67-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 26165-67-3(Hazardous Substances Data)

Usage

General Description

4-(2,5-dimethyl-1H-pyrrol-1-yl)benzohydrazide is a chemical compound with the molecular formula C14H16N4O. It is commonly used as an intermediate in the synthesis of pharmaceutical compounds. This chemical has a benzene ring with a hydrazide group and a pyrrole ring attached, making it useful for various medicinal applications. It has potential applications in the development of drugs for conditions such as cancer and diabetes. Additionally, it has shown promise in the field of organic chemistry for the creation of new compounds with diverse chemical properties and biological activities.

InChI:InChI=1/C13H15N3O/c1-9-3-4-10(2)16(9)12-7-5-11(6-8-12)13(17)15-14/h3-8H,14H2,1-2H3,(H,15,17)

Upstream product

• 26165-66-2 methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate 
• 5159-70-6 ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate 
• 110-13-4 2,5-hexanedione 
• 94-09-7 p-aminoethylbenzoate 
• 150-13-0 4-amino-benzoic acid 
• 15898-26-7 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 

Downstream Products

• 1246958-21-3 N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethanocycloprop[f]isoindol-2-(1H)-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide 
• 1312761-44-6 N'-[4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoyl]-2-(1H-indol-3-yl)-2-oxoacetohydrazide 
• 1159693-69-2 N-(2,5-dimethyl-pyrrol-1-yl)-4-(2,5-dimethylpyrrol-1-yl)benzamide 
• 1383714-64-4 C₂₆H₂₃N₃O 
• 1383714-65-5 4-(2,5-dimethylpyrrol-1-yl)benzoic acid[1-(4-aminophenyl)ethylidene]hydrazide 
• 474891-25-3 N'-(propan-2-ylidene)-4-(1H-2,5-dimethylpyrrol-1-yl)benzohydrazide 
• 926388-36-5 N'-(1-methylbenzylidene)-4-(1H-2,5-dimethylpyrrol-1-yl)benzohydrazide 
• 1383714-67-7 4-amino-5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-2,4-dihydro-1,2,4-triazole-3-thione 
• 1383714-66-6 5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-1,3,4-oxadiazole-2-thiol 
• 880046-41-3 N'-(benzylidene)-4-(1H-2,5-dimethylpyrrol-1-yl)benzohydrazide 
• 1383714-68-8 3-acetyl-5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-2-phenyl-2,3-dihydro-1,3,4-oxadiazole 
• 880023-68-7 N'-(2-chlorobenzylidene)-4-(1H-2,5-dimethylpyrrol-1-yl)benzohydrazide 
• 1383714-69-9 3-acetyl-5-[4-(2,5-dimethylpyrrol-1-yl)phenyl]-2-(2-chlorophenyl)-2,3-dihydro-1,3,4-oxadiazole 
• 478934-56-4 N'-(4-bromobenzylidene)-4-(1H-2,5-dimethylpyrrol-1-yl)benzohydrazide 

Relevant articles and documents

Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst

A bifunctional 3d-metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr-C@SiO2-L is obtained by pyrolysis of a cobalt-impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson-Kass condensation provides >40 pyrroles in good to high yields using dihydrogen, formic acid, or a CO/H2O mixture (WGSR conditions) as reductant. In addition to the favorable step economy, this straightforward domino process does not require any solvents or external co-catalysts. The general synthetic utility of this methodology was demonstrated on a variety of functionalized substrates including the preparation of biologically active and pharmaceutically relevant compounds, for example, (+)-Isamoltane.

Synthesis and antitubercular activity of some N'-substituted benzoyl-4-(2,5dimethyl-1H-pyrrolyl) benzohydrazide Derivatives

Some new substituted dimethylpyrrolyl benzohydrazide derivatives have been synthesized as new antitubercular agents. Dimethylpyrrolyl benzohydrazide derivatives 4(a-j) were synthesized by the reaction of 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzohydrazide (3) with substituted benzoic acids in N', N'-dimethyl formamide using 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, an amide coupling agent and N',N'-Diisopropylethylamine as a catalyst. All the newly synthesized compounds 4(a-j) were screened for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv and compounds have exhibited significant minimum inhibitory concentration values.

Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents

In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.