21018-13-3

Basic information

• Product Name: 2-Ethoxybenzhydrazide
• Synonyms: O-ETHOXY BENZHYDRAZIDE;AKOS B014935;2-ETHOXYBENZHYDRAZIDE;2-ETHOXYBENZOYL HYDRAZINE;ART-CHEM-BB B014935;BENZOIC ACID, 2-ETHOXY-, HYDRAZIDE;2-Ethoxybenzohydrazide;o-Ethoxybenzoylhydrazine
• CAS NO: 21018-13-3
• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 180.2
• EINECS: 1533716-785-6
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 21018-13-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 62-64°C
• Appearance: /
• Density: 1.144 g/cm³
• Refractive Index: 1.549
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.46±0.10(Predicted)
• CAS DataBase Reference: 2-Ethoxybenzhydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxybenzhydrazide(21018-13-3)
• EPA Substance Registry System: 2-Ethoxybenzhydrazide(21018-13-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 21018-13-3(Hazardous Substances Data)

Usage

General Description

2-Ethoxybenzhydrazide is a chemical compound with the molecular formula C11H15NO2. It is a benzhydrazide derivative, and is commonly used as a building block in the synthesis of various pharmaceutical compounds. 2-Ethoxybenzhydrazide is also used as an intermediate in the production of dyes, pigments, and other chemical products. It is a white to light brown crystalline powder, and is soluble in most organic solvents. Additionally, 2-Ethoxybenzhydrazide has potential applications in the field of agriculture as a pesticide or herbicide.

InChI:InChI=1/C9H12N2O2/c1-2-13-8-6-4-3-5-7(8)9(12)11-10/h3-6H,2,10H2,1H3,(H,11,12)

Upstream product

• 6290-24-0 ethyl 2-ethoxybenzoate 
• 3686-55-3 methyl 2-ethoxybenzoate 
• 134-11-2 2-ethoxybenzoic acid 

Downstream Products

• 19982-34-4 5-(2-ethoxy-phenyl)-3H-[1,3,4]oxadiazol-2-one 
• 19982-38-8 2-(o.etossifenil)-5-mercapto-1,3,4-oxadiazolo 
• 18233-21-1 2-(2-ethoxy-phenyl)-5-methyl-[1,3,4]oxadiazole 
• 18233-26-6 2-(2-ethoxy-phenyl)-5-phenyl-[1,3,4]oxadiazole 
• 139213-45-9 2-(2-Ethoxy-benzoyl)-5-isopropyl-8-methyl-1,2-dihydro-benzo[4,5]furo[3,2-c]pyrazol-3-one 
• 946501-45-7 N'-(2-ethoxybenzoyl)-5-(trifluoroacetyl)thiophene-2-carbohydrazide 
• 512845-06-6 5-amino-1-(2-phenylethyl)-4-[3-(2-ethoxyphenyl)-1,2,4-triazolo-5-yl]pyrazole 
• 512844-88-1 7-(2-phenylethyl)-2-(2-ethoxyphenyl)pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine 
• 19982-29-7 [5-(2-ethoxy-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-acetic acid 
• 19982-28-6 [5-(2-ethoxy-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-acetic acid hydrazide 
• 19982-30-0 [5-(2-ethoxy-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-acetic acid ethyl ester 
• 19982-37-7 2-(2-ethoxy-phenyl)-5-ethylsulfanyl-[1,3,4]oxadiazole 
• 19982-33-3 2-ethanesulfonyl-5-(2-ethoxy-phenyl)-[1,3,4]oxadiazole 
• 19982-36-6 2-(2,4-dinitro-phenylsulfanyl)-5-(2-ethoxy-phenyl)-[1,3,4]oxadiazole 

Relevant articles and documents

From Oxadiazole to Triazole Analogues: Optimization toward a Dual Orexin Receptor Antagonist with Improved in vivo Efficacy in Dogs

The orexin system is responsible for regulating the sleep-wake cycle. Suvorexant, a dual orexin receptor antagonist (DORA) is approved by the FDA for the treatment of insomnia disorders. Herein, we report the optimization efforts toward a DORA, where our starting point was (5-methoxy-4-methyl-2-[1,2,3]triazol-2-yl-phenyl)-{(S)-2-[5-(2-trifluoromethoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrrolidin-1-yl}methanone (6), a compound which emerged from our in-house research program. Compound 6 was shown to be a potent, brain-penetrating DORA with in vivo efficacy similar to suvorexant in rats. However, shortcomings from low metabolic stability, high plasma protein binding (PPB), low brain free fraction (fu brain), and low aqueous solubility, were identified and hence, compound 6 was not an ideal candidate for further development. Our optimization efforts addressing the above-mentioned shortcomings resulted in the identification of (4-chloro-2-[1,2,3]triazol-2-yl-phenyl)-{(S)-2-methyl-2-[5-(2-trifluoromethoxy-phenyl)-4H-[1,2,4]triazol-3-yl]-pyrrolidin-1-yl}l-methanone (42), a DORA with improved in vivo efficacy compared to 6.

Ultrasound-assisted, convenient and widely applicable 1,1′-carbonyl-diimidazole-mediated "One-pot" syntheses of acyl/sulfonyl hydrazines

Acyl / sulfonyl hydrazines were synthesized in a one-pot reaction from carboxylic acid/aryl sulfonic acid in the presence of 1,1′-carbonyl diimidazole (CDI) under ultrasound as well as under conventional heating. The reaction was performed on diverse organic molecules including simple benzoic acid (1), electron-donating and electron-withdrawing substituted benzoic acids, biologically active compounds like coumarin-3-carboxylic acid (12), 7-hydroxycoumarin-4-acetic acid (13), and therapeutic drugs like ibuprofen (14), flurbiprofen (15), naproxen (16) or tricyclic adamantane carboxylic acid (17). Benzene sulfonic acid (18) and its derivatives (19, 20, 21 and 22) were used to prepare corresponding sulfonyl hydrazide. All products were synthesized in very good yield via ultrasonic irradiation method and characterized by spectroscopic techniques including EIMS, 1H NMR, 13C NMR, IR. The method was found very simple, facile, efficient and high yielding (>90).

Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents

A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 ± 0.2, 30.0 ± 1.2, 18.3 ± 1.4 μM, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 μM, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 μg/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study.