2924-16-5 | 3-Fluorophenylhydrazine hydrochloride

CAS:2924-16-5 | 3-Fluorophenylhydrazine hydrochloride,Description

(3-Fluorophenyl)hydrazine hydrochloride is not directly mentioned in the provided papers, but it is related to the chemical class of hydrazine derivatives. These compounds are known for their applications in the synthesis of pharmaceuticals, pesticides, and energetic materials. They are characterized by the presence of a hydrazine group (-NH-NH2) attached to an aromatic ring that in this case would be a phenyl ring with a fluorine substituent.

Synthesis Analysis

The synthesis of hydrazine derivatives can be complex, involving multiple steps such as acylation, chlorination, diazotization, and reduction reactions. For instance, the synthesis of 4-chloro-2-fluorophenylhydrazine, a compound similar to (3-fluorophenyl)hydrazine, involves starting with 2-fluoroaniline, which undergoes acylation and chlorination, followed by hydrolysis and diazotization, and finally reduction to yield the target hydrazine derivative.

Molecular Structure Analysis

The molecular structure of hydrazine derivatives is typically confirmed using various spectroscopic techniques such as IR, 1H NMR, 13C NMR, and sometimes crystallographic studies. These methods provide detailed information about the molecular framework and the nature of substituents on the aromatic ring.

Chemical Reactions Analysis

Hydrazine derivatives can participate in various chemical reactions due to their reactive hydrazine group. They can be used as precursors for the synthesis of high-performance energetic materials, as seen in the synthesis of 1,2-bis(2,4,6-trinitrophenyl) hydrazine, which is a precursor for hexanitrazobenzene. They can also react with different reagents to form a variety of structurally isomeric compounds, as demonstrated by the reactions of (di-tert1-butylfluorosilyl)hydrazine with chlorosilanes and lithiated compounds.

Physical and Chemical Properties Analysis

The physical properties such as melting points and yields of hydrazine derivatives are determined after synthesis. For example, 4-chloro-2-fluorophenylhydrazine has a melting point range of 59-60°C and a high yield, indicating the effectiveness of the synthesis method. The chemical properties, including reactivity and potential biological activity, are assessed through computational studies and biological testing. Some hydrazine derivatives exhibit antimicrobial activity and can influence cell proliferation, which is significant for pharmaceutical applications.

Scientific Research Applications

• Fluorescent Probing and Detection : (3-Fluorophenyl)hydrazine hydrochloride and related compounds have been utilized in the development of fluorescent probes. For instance, Zhu et al. (2019) designed a ratiometric fluorescent probe for N2H4 detection, showcasing low cytotoxicity and high sensitivity, suitable for environmental and cellular applications (Zhu et al., 2019). Another study by Wu et al. (2019) developed a quinoline-derived probe for hydrazine detection with a large emission shift, demonstrating its potential in environmental and biological sample analysis (Wu et al., 2019).
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• Cytotoxic and Antioxidant Evaluation : A study by Journals Iosr et al. (2015) involved synthesizing new heterocyclic compounds, including those derived from (3-Fluorophenyl)hydrazine, to evaluate their cytotoxic and antioxidant activities, indicating its relevance in pharmaceutical research (Journals Iosr et al., 2015).
• Antimicrobial Activity : Dinnimath et al. (2011) synthesized 3-chloro-4-fluoro phenyl hydrazine and its derivatives to screen for antimicrobial activities, demonstrating the potential use of these compounds in developing new antimicrobial agents (Dinnimath et al., 2011).
• Fluorescent Labeling in Chromatography : Tsuruta et al. (1993) explored the use of benzohydrazide derivatives, related to (3-Fluorophenyl)hydrazine, as fluorescent labeling reagents in high-performance liquid chromatography (HPLC), indicating its analytical applications (Tsuruta et al., 1993).
• Environmental and Biological Monitoring : Various studies have highlighted the application of (3-Fluorophenyl)hydrazine-related compounds in environmental and biological monitoring. For example, a study by Nguyen et al. (2018) reviewed the development of fluorescent probes for hydrazine, emphasizing their importance in monitoring environmental and health hazards (Nguyen et al., 2018).
• Medicinal Chemistry : Surmont et al. (2010) described a new synthesis method for fluorinated pyrazoles using (3-Fluorophenyl)hydrazine-related compounds, underlining the significance of these compounds in medicinal chemistry applications (Surmont et al., 2010).

Safety And Hazards

“(3-Fluorophenyl)hydrazine hydrochloride” is toxic if swallowed, in contact with skin, or if inhaled. It causes skin irritation, serious eye irritation, and may cause respiratory irritation.

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