129564-33-6

Basic information

• Product Name: 2-(3,4-DICHLOROPHENYL)ETHANOHYDRAZIDE
• Synonyms: 2-(3,4-DICHLOROPHENYL)ETHANOHYDRAZIDE;2-(3,4-dichlorophenyl)ethanehydrazide;IVK/9085983;Maybridge1_000004;MixCom1_000004;Oprea1_580984;ZINC00128974
• CAS NO: 129564-33-6
• Molecular Formula: C₈H₈Cl₂N₂O
• Molecular Weight: 219.06792
• Mol File: 129564-33-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 424.2 °C at 760 mmHg
• Flash Point: 210.4 °C
• Appearance: /
• Density: 1.406g/cm³
• Vapor Pressure: 2.1E-07mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(3,4-DICHLOROPHENYL)ETHANOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-DICHLOROPHENYL)ETHANOHYDRAZIDE(129564-33-6)
• EPA Substance Registry System: 2-(3,4-DICHLOROPHENYL)ETHANOHYDRAZIDE(129564-33-6)

Safety Data

• Hazardous Substances Data: 129564-33-6(Hazardous Substances Data)

Usage

General Description

2-(3,4-Dichlorophenyl)ethanohydrazide, also known as ethanohydrazide or ethanohydrazide, is a chemical compound with the formula C8H9Cl2N2O. It is a white to off-white crystalline powder that is insoluble in water. 2-(3,4-DICHLOROPHENYL)ETHANOHYDRAZIDE is primarily used as a hydrazine derivative and a building block in the synthesis of various pharmaceuticals and agrochemicals. It is also used in the production of insecticides and herbicides. Additionally, it has potential applications in the treatment of certain diseases such as cancer, tuberculosis, and neurodegenerative disorders due to its ability to inhibit the activity of certain enzymes. However, ethanohydrazide is considered to be toxic if ingested, inhaled, or comes into contact with the skin, and should be handled with caution.

InChI:InChI=1/C8H8Cl2N2O/c9-6-2-1-5(3-7(6)10)4-8(13)12-11/h1-3H,4,11H2,(H,12,13)

Upstream product

• 6725-45-7 ethyl 3,4-dichlorophenylacetate 
• 6725-44-6 methyl 2-(3,4-dichlorophenyl)acetate 
• 5807-30-7 3,4-dichlorophenyl acetic acid 

Downstream Products

• 1456613-99-2 2-(3,4-dichlorobenzyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one 
• 1456614-21-3 C₁₃H₁₃Cl₂N₅O₂S 
• 502686-15-9 C₉H₈Cl₂N₄ 

Relevant articles and documents

Discovery of a 3,4,5-trisubstituted-1,2,4-triazole agonist with high affinity and selectivity at the somatostatin subtype-4 (sst4) receptor

A series of compounds containing a 1,2,4-triazole moiety were synthesized, targeting the somatostatin receptor subtype-4 (sst4). Compounds were developed in which the Phe6/Phe7/Phe11, Trp8, and Lys9 mimetic groups were interchanged at positions 3, 4, and 5 of the 1,2,4-triazole ring. The 1,2,4-triazoles containing an 2-(imidazol-4-yl)ethyl substituent at position-3 demonstrated moderate binding affinity at sst4. 1,2,4-Triazoles containing an (indol-3-yl)methyl substituent at position-5 lacked affinity at sst4. The 1,2,4-triazoles containing an aminopropyl group at position-4 showed enhanced binding affinity compared to the 3-position. One compound with an 3-(imidazol-4-yl)propyl group at position-4 (compound 44) imparted high affinity and selectivity at sst4 (sst2A = >10000 nM; sst4 = 19 nM), acting as an agonist (EC50 = 6.8 nM). Docking 44 into a model-built structure of sst4 pointed to differences in its binding versus the other low-affinity compounds and was also in line with one of the two previously reported binding modes. A virtual screening (VS) experiment, employing two separate docking algorithms, was able to score 44 among the top-ranked poses. In summary, compound 44 represents a novel and promising lead structure towards the development of a clinically viable sst4 agonist for the treatment of conditions ranging from Alzheimer's disease to chronic pain.

Synthesis and structure-activity relationships of 3,4,5-trisubstituted-1,2,4-triazoles: High affinity and selective somatostatin receptor-4 agonists for Alzheimer's disease treatment

Somatostatin receptor-4 (SST4) is highly expressed in brain regions affiliated with learning and memory. SST4 agonist treatment may act to mitigate Alzheimer's disease (AD) pathology. An integrated approach to SST4 agonist lead optimization is presented herein. High affinity and selective agonists with biological efficacy were identified through iterative cycles of a structure-based design strategy encompassing computational methods, chemistry, and preclinical pharmacology. 1,2,4-Triazole derivatives of our previously reported hit (4) showed enhanced SST4 binding affinity, activity, and selectivity. Thirty-five compounds showed low nanomolar range SST4 binding affinity, 12 having a Ki 500-fold affinity for SST4 as compared to SST2A. SST4 activities were consistent with the respective SST4 binding affinities (EC50 600-fold selectivity over SST2A) display a favorable physiochemical profile, and was advanced to learning and memory behavior evaluations in the senescence accelerated mouse-prone 8 model of AD-related cognitive decline. Chronic administration enhanced learning with i.p. dosing (1 mg kg-1) compared to vehicle. Chronic administration enhanced memory with both i.p. (0.01, 0.1, 1 mg kg-1) and oral (0.01, 10 mg kg-1) dosing compared to vehicle. This study identified a novel series of SST4 agonists with high affinity, selectivity, and biological activity that may be useful in the treatment of AD. This journal is

Synthesis & characterization of 2-(substituted-phenyl)acetohydrazide analogs, 1,3,4-oxadiazoles, and 1,2,4-triazine Ring Systems: A novel class of potential analgesic and anti-inflammatory agents

The new series of 2-(substituted-phenyl)acetohydrazides analogs, S-alkylated 5-substituted-1,3,4-oxadiazoles-2-thione derivatives and 5-arylidene-3-substituted-1,2,4-triazines have been synthesized in good yields and characterized by IR, NMR, mass spectral and elemental analyses. All the synthesized compounds 4(a-d), 5(a-d), 7(a-b), and 8(a-f) are evaluated for their in vitro DPPH scavenging, antimicrobial activity, in vivo analgesic, anti-inflammatory activities. The results of the anti-inflammatory activity are supported by molecular docking study with mouse COX-1 (PDB ID: 2CZT) and COX-2 (PDB ID: 3LN1) enzymes to predict their putative interactions. Among all the assays conducted, the compounds 5-(4-bromophenyl)-3-(naphthalen-2-ylmethyl)-1,2,4-triazine (4d) and2-{[5-(diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide (8a) have emerged as the most potent molecules.