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

Description

4-Fluorobenzhydrazide is an organic compound with the chemical formula C7H7FN2O. It is a derivative of benzene, featuring a fluorine atom attached to the 4-position, and a hydrazide group attached to the 1-position. 4-Fluorobenzhydrazide is known for its potential applications in various chemical and pharmaceutical processes due to its unique structure and properties.

Uses

Used in the Synthesis of Fluorinated Polymers:
4-Fluorobenzhydrazide is used as a key intermediate in the synthesis of fluorinated poly(1,3,4-oxadiazole-ether-imide). This polymer is a high-performance material with excellent thermal stability, mechanical properties, and chemical resistance, making it suitable for various applications, such as aerospace, automotive, and electronics industries.
In the synthesis process, 4-Fluorobenzhydrazide serves as a solvent for the reaction between N-(3,5-dinitrobenzoyl)-N'-(4-fluorobenzoyl)-hydrazine and itself in N-methyl-2-pyrrolidone (NMP). This reaction leads to the formation of the desired fluorinated poly(1,3,4-oxadiazole-ether-imide), which exhibits improved properties compared to non-fluorinated counterparts.
While the provided materials do not explicitly mention other applications, 4-Fluorobenzhydrazide may also have potential uses in the pharmaceutical industry, given its structural similarity to other hydrazide compounds that have been studied for their biological activities. Further research and development could reveal additional applications for this versatile compound.

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%).

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

Downstream Products

• 80791-32-8 N'-(4-Fluoro-benzoyl)-hydrazinecarbodithioic acid nonyl ester 
• 84919-25-5 N’-(2-oxo-1,2-dihydro-indol-3-ylidene)-4-fluorobenzohydrazide 
• 831-38-9 2-(4-fluorobenzoyl)hydrazinecarbothioamide 
• 934842-40-7 C₁₈H₂₂FN₃OS 
• 61019-25-8 4-amino-5-(3-fiuorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiol 

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.

Iron-catalyzed oxidative amidation of acylhydrazines with amines

A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.

Carbazole-based semicarbazones and hydrazones as multifunctional anti-Alzheimer agents

With the aim to combat a multi-faceted neurodegenerative Alzheimer’s disease (AD), a series of carbazole-based semicarbazide and hydrazide derivatives were designed, synthesized and assessed for their cholinesterase (ChE) inhibitory, antioxidant and biometal chelating activity. Among them, (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(pyridin-2-yl)hydrazinecarbothioamide (62) and (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(5-chloropyridin-2-yl)hydrazinecarbothioamide (63) emerged as the premier candidates with good ChE inhibitory activities (IC50 values of 1.37 μM and 1.18 μM for hAChE, IC50 values of 2.69 μM and 3.31 μM for EqBuChE, respectively). All the test compounds displayed excellent antioxidant activity (reduction percentage of DPPH values for compounds (62) and (63) were 85.67% and 84.49%, respectively at 100 μM concentration). Compounds (62) and (63) conferred specific copper ion chelating property in metal chelation study. Molecular docking studies of compounds (62) and (63) indicate strong interactions within the active sites of both the ChE enzymes. Besides that, these compounds also exhibited significant in silico drug-like pharmacokinetic properties. Thus, taken together, they can serve as a starting point in the designing of multifunctional ligands in pursuit of potential anti-AD agents that might further prevent the progression of ADs. Communicated by Ramaswamy H. Sarma.