456-06-4

Basic information

• Product Name: 4-Fluorobenzhydrazide
• Synonyms: ASISCHEM R36621;BUTTPARK 35\03-73;4-FLUOROBENZENECARBOHYDRAZIDE;4-FLUOROBENZOYLHYDRAZINE HYDRATE;4-FLUOROBENZHYDRAZIDE;4-FLUOROBENZOHYDRAZIDE HYDRATE;4-FLUOROBENZOIC HYDRAZIDE;4-FLUOROBENZOIC HYDRAZIDE HYDRATE
• CAS NO: 456-06-4
• Molecular Formula: C₇H₇FN₂O
• Molecular Weight: 154.14
• EINECS: 207-258-5
• Product Categories: Fluorobenzene;Phenyls & Phenyl-Het;Benzenes;Fluorine Compounds;Phenyls & Phenyl-Het;Carbonyl Compounds;Hydrazides;Organic Building Blocks
• Mol File: 456-06-4.mol
• Article Data: 147

Chemical Properties

• Melting Point: 162-166 °C(lit.)
• Boiling Point: 299.8 °C at 760 mmHg
• Flash Point: 135.1 °C
• Appearance: Orange to light brown/Crystalline Powder
• Density: 1.272 g/cm³
• Vapor Pressure: 0.392mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• PKA: 12.17±0.10(Predicted)
• CAS DataBase Reference: 4-Fluorobenzhydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorobenzhydrazide(456-06-4)
• EPA Substance Registry System: 4-Fluorobenzhydrazide(456-06-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DH1310000
• HazardClass: IRRITANT
• Hazardous Substances Data: 456-06-4(Hazardous Substances Data)

Usage

preparation

The synthesized ester (12.5ml) was taken into a round ?bottom flask (250ml), 50ml of absolute ethanol & ?37.5ml of hydrazine hydrate was added in the flask. ?The ester, ethanol & hydrazine hydrate for the synthesis of hydrazide must be in following ratio: Ester: Absolute ethanol: Hydrazine hydrate 1 : 4 : 3 ?Then round bottom flask was covered with aluminium ?foil, placed on hot plate & allowed to stir it for almost ?12-15 hrs. As the solid product appeared, reaction ?completion was checked by performing TLC using n-hexane, ethyl acetate & TLC cards & observed under ?UV lamp. After completion of reaction n-hexane was added. ?Solution filtered as needle like crystals appeared. ?Allowed it to dry & a shiny off white product was ?obtained that was hydrazide & product was calculated ?(79%).

Chemical Properties

White solid

Uses

Used in the stnthesis of fluorinated poly (1, 3, 4-oxadiazole-ether-imide). N-(3,5-dinitrobenzoyl)-N?-(4-fluorobenzoyl)-hydrazine with 4-Fluorobenzhydrazide as solvent in NMP.

InChI:InChI=1/C7H5Cl2F/c8-7(9)5-1-3-6(10)4-2-5/h1-4,7H

Upstream product

• 2714-90-1 phenyl 4-fluorobenzoate 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 459-57-4 4-fluorobenzaldehyde 
• 90172-63-7 1-(p-fluorophenylcarbonyl)imidazole 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 403-43-0 4-fluorobenzoyl chloride 
• 456-22-4 4-Fluorobenzoic acid 
• 403-33-8 methyl 4-flurobenzoate 
• 451-46-7 4-fluorobenzoic acid ethyl ester 

Downstream Products

• 41421-13-0 5-(4-fluorophenyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione 
• 41421-13-0 2-mercapto-5-(4-fluorophenyl)-1,3,4-oxadiazole 
• 934842-40-7 C₁₈H₂₂FN₃OS 
• 1010800-22-2 2-(4-fluorophenyl)-1,3,4-thiadiazole 
• 595567-05-8 2-(4-fluorobenzene)-1,3,4-oxadiazole 
• 1580-50-3 2-(4-fluorophenyl)-5-phenyl-1,3,4-oxadiazole 
• 1010800-20-0 C₁₀H₉FN₂O 

Relevant articles and documents

Synthesis, spectral analysis, antibacterial, antifungal, antioxidant and hemolytic activity studies of some new 2,5-disubstituted-1,3,4-oxadiazoles

Series of 1,3,4-oxadiazole derivatives (5a–5g and 5h, 5i) were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and HR-MS spectral analysis. All the target compounds were screened for their in vitro antibacterial activity against two Gram-negative bacterial strains namely Escherichia coli (MTCC 405) and Salmonella typhi (MTCC 3224) and two Gram-positive bacterial strains namely Bacillus subtilis (MTCC 1790) and Bacillus megaterium (MTCC 1684) and antifungal activity against Aspergillus niger (MTCC 282), Rhizopus oryzae (MTCC 262), Penicillium chrysogenum (MTCC 974), and Candida albicans (MTCC 183) fungal strains. The synthesized compounds exhibited significant antibacterial and antifungal potential. Three compounds (5e, 5f and 5g) have shown higher antibacterial activity with very low MIC values comparable to streptomycin. According to the SAR study, the antibacterial efficacy can be intensified by substituting fluoro and methyl substituents at the para position in acid hydrazide. The synthesized compounds were also screened for % radical scavenging activity by OH and DPPH assay and found to be good antioxidant agents. Besides, the hemolytic study revealed that the synthesized 1,3,4-oxadiazoles possessed negligible cytotoxicity compared with the standard.

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.

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.