59670-13-2

Basic information

• Product Name: 1-(3-methylbenzylidene)-2-phenylhydrazine
• CAS NO: 59670-13-2
• Molecular Formula: C₁₄H₁₄N₂
• Molecular Weight: 210.2744
• Mol File: 59670-13-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 351°C at 760 mmHg
• Flash Point: 166.1°C
• Density: 1g/cm³
• Vapor Pressure: 4.24E-05mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 1-(3-methylbenzylidene)-2-phenylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-methylbenzylidene)-2-phenylhydrazine(59670-13-2)
• EPA Substance Registry System: 1-(3-methylbenzylidene)-2-phenylhydrazine(59670-13-2)

Safety Data

• Hazardous Substances Data: 59670-13-2(Hazardous Substances Data)

Usage

General Description

1-(3-methylbenzylidene)-2-phenylhydrazine is an organic compound with the chemical formula C14H14N2. It is a hydrazine derivative and features a substituted benzylidene group and a phenyl group. 1-(3-methylbenzylidene)-2-phenylhydrazine is often used in organic synthesis as a starting material for the preparation of various heterocyclic compounds. It has also been studied for its potential pharmaceutical applications, particularly in the field of medicinal chemistry. Additionally, 1-(3-methylbenzylidene)-2-phenylhydrazine has been investigated for its antimicrobial and insecticidal properties. Overall, this compound holds importance as a versatile intermediate in chemical and pharmaceutical industries.

Upstream product

• 620-23-5 m-tolyl aldehyde 
• 100-63-0 phenylhydrazine 
• 587-03-1 3-methylbenzyl alcohol 
• 620-19-9 1-chloromethyl-3-methyl-benzene 

Downstream Products

• 59670-14-3 N-Methyl-N-phenyl-N'-[1-m-tolyl-meth-(E)-ylidene]-hydrazine 
• 1569776-85-7 C₁₄H₁₁Br₃N₂ 
• 1416008-46-2 tert-butyl 4'-tert-butyl-2-oxo-2'-phenyl-5'-m-tolyl-2',4'-dihydrospiro[indoline-3,3'-pyrazole]-1-carboxylate 
• 25939-10-0 3-methyl-N'-phenylbenzohydrazonoyl chloride 

Relevant articles and documents

Identification of novel 1,3-diaryl-1,2,4-triazole-capped histone deacetylase 6 inhibitors with potential anti-gastric cancer activity

Histone deacetylase 6 (HDAC6) has emerged as a critical regulator of many cellular pathways in tumors due to its unique structure basis and abundant substrate types. Over the past few decades, the role played by HDAC6 inhibitors as anticancer agents has sparked great interest of biochemists worldwide. However, they were less reported for gastric cancer therapy. In this paper, with the help of bioisosteric replacement, in-house library screening, and lead optimization strategies, we designed, synthesized and verified a series of 1,3-diaryl-1,2,4-triazole-capped HDAC6 inhibitors with promising anti-gastric cancer activities. Amongst, compound 9r displayed the best inhibitory activity towards HDAC6 (IC50 = 30.6 nM), with 128-fold selectivity over HDAC1. Further BLI and CETSA assay proved the high affinity of 9r to HDAC6. In addition, 9r could dose-dependently upregulate the levels of acetylated α-tubulin, without significant effect on acetylated histone H3 in MGC803 cells. Besides, 9r exhibited potent antiproliferative effect on MGC803 cells, and promoted apoptosis and suppressed the metastasis without obvious toxicity, suggesting 9r would serve as a potential lead compound for the development of novel therapeutic agents of gastric cancer.

Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines

Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.

Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles

Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.