5814-05-1

Basic information

• Product Name: 2-Chlorobenzhydrazide
• Synonyms: Benzoic acid, 2-chloro-, hydrazide;o-Chlorobenzhydrazide;2-CHLOROBENZOIC HYDRAZIDE;2-CHLOROBENZENE-1-CARBOHYDRAZIDE;2-CHLOROBENZOIC ACID HYDRAZIDE;2-CHLOROBENZHYDRAZIDE;2-CHLOROBENZOHYDRAZIDE;(O-CHLOROBENZOYL)HYDRAZINE
• CAS NO: 5814-05-1
• Molecular Formula: C₇H₇ClN₂O
• Molecular Weight: 170.6
• EINECS: 227-380-2
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Chlorine Compounds;Carbonyl Compounds;Hydrazides;Organic Building Blocks
• Mol File: 5814-05-1.mol
• Article Data: 124

Chemical Properties

• Melting Point: 113-118 °C
• Boiling Point: 345.4 °C at 760 mmHg
• Flash Point: 162.7 °C
• Appearance: White to slightly beige/Crystalline Powder
• Density: 1.323 g/cm³
• Vapor Pressure: 2.35E-05mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• BRN: 972229
• CAS DataBase Reference: 2-Chlorobenzhydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzhydrazide(5814-05-1)
• EPA Substance Registry System: 2-Chlorobenzhydrazide(5814-05-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• HazardClass: IRRITANT
• Hazardous Substances Data: 5814-05-1(Hazardous Substances Data)

Usage

Chemical Properties

White to slightly beige crystalline powder

InChI:InChI=1/C7H7ClN2O/c8-6-4-2-1-3-5(6)7(11)10-9/h1-4H,9H2,(H,10,11)

Upstream product

• 7335-25-3 ethyl 2-chlorobenzoate 
• 610-96-8 methyl chlorobenzoate 
• 609-65-4 o-chlorobenzoyl chloride 
• 609-66-5 2-chlorobenzamide 
• 2136-89-2 2-chlorobenzotrichloride 
• 64-17-5 ethanol 
• 118-91-2 ortho-chlorobenzoic acid 
• 861408-91-5 C₁₂H₁₅ClN₂O₃ 

Downstream Products

• 93417-99-3 furfural-(2-chloro-benzoylhydrazone) 
• 82973-09-9 2-chloro-benzoic acid benzylidenehydrazide 
• 82859-77-6 (E)-2-chloro-N'-(2-hydroxybenzylidene)benzohydrazide 
• 130489-65-5 2-chloro-benzoic acid butylidenehydrazide 
• 100375-31-3 N-benzenesulfonyl-N'-(2-chloro-benzoyl)-hydrazine 
• 103038-97-7 2-chloro-benzoic acid isopropylidenehydrazide 
• 130158-98-4 2-chloro-benzoic acid-[1-(4-methoxy-phenyl)-ethylidenehydrazide] 
• 49747-51-5 o-chlorobenzoyl azide 
• 89-98-5 2-chloro-benzaldehyde 
• 609-65-4 o-chlorobenzoyl chloride 
• 40833-32-7 1-(o-Chlorbenzoyl)-4-phenyl-selenosemicarbazid 

Relevant articles and documents

Synthesis, crystal structure, DNA interaction and anticancer evaluation of pyruvic acid derived hydrazone and its transition metal complexes

A novel tridentate chelating ligand, Ethyl 2-(2-(2-chlorobenzoyl)hydrazono)propanoate and its late transition metal complexes were synthesized, characterized and evaluated for anticancer behavior. The structures were elucidated with the help of elemental analyses, spectral (vibrational, electronic, NMR and mass) and thermo-gravimetric techniques. Single crystal X-ray crystallographic studies of the ligand suggest an orthorhombic lattice structure with Pna21 space group. The interaction of ligand and complexes with DNA (CT-DNA) has been extensively studied using absorption, emission, viscosity and thermal denaturation studies with E. coli DNA. The DNA cleavage ability of ligand and metal complexes was tested using plasmid pBR322 DNA by gel electrophoresis method. The ligand and its copper complex have been evaluated for their in vitro anticancer activity against human cancer cells of different origin such as KB (Oral), A431 (Skin), Mia-Pa-Ca (Pancreases), K-549 (Lung), K-562 (Leukemia), MCF-7 (Breast) and VERO by MTT assay and the apoptosis assay was carried out with acridine orange/ethidium bromide (AO/EB) staining method. The studies suggest that ligand and copper complex exhibit significant cytotoxic activity on KB, MCF-7, A-431, Mia-Pa-Ca-2 an d A-549 cell lines compared to K-562 and VERO cell lines.

Development of phenyltriazole thiol-based derivatives as highly potent inhibitors of DCN1-UBC12 interaction

Defective in cullin neddylation 1(DCN1) is a co-E3 ligase that is important for cullin neddylation. Dysregulation of DCN1 highly correlates with the development of various cancers. Herein, from the initial high-throughput screening, a novel hit compound 5a containing a phenyltriazole thiol core (IC50 value of 0.95 μM for DCN1-UBC12 interaction) was discovered. Further structure-based optimization leads to the development of SK-464 (IC50 value of 26 nM). We found that SK-464 not only directly bound to DCN1 in vitro, but also engaged cellular DCN1, suppressed the neddylation of cullin3, and hindered the migration and invasion of two DCN1-overexpressed squamous carcinoma cell lines (KYSE70 and H2170). These findings indicate that SK-464 may be a novel lead compound targeting DCN1-UBC12 interaction.

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.