371-14-2

Basic information

• Product Name: 4-FLUOROPHENYLHYDRAZINE
• Synonyms: 1-(4-FLUOROPHENYL)HYDRAZINE;4-FLUOROPHENYLHYDRAZINE;AKOS BBS-00006439;N-(4-Fluorophenyl)hydrazine;Hydrazine, (4-fluorophenyl)-;4-Fluorophenylhydrazin
• CAS NO: 371-14-2
• Molecular Formula: C₆H₇FN₂
• Molecular Weight: 126.13
• EINECS: 206-732-9
• Mol File: 371-14-2.mol
• Article Data: 32

Chemical Properties

• Melting Point: 36.8 °C
• Boiling Point: 227℃
• Flash Point: 91℃
• Appearance: /
• Density: 1.257
• Vapor Pressure: 0.0805mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 5.24±0.20(Predicted)
• CAS DataBase Reference: 4-FLUOROPHENYLHYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUOROPHENYLHYDRAZINE(371-14-2)
• EPA Substance Registry System: 4-FLUOROPHENYLHYDRAZINE(371-14-2)

Safety Data

• Hazardous Substances Data: 371-14-2(Hazardous Substances Data)

Usage

Description

4-FLUOROPHENYLHYDRAZINE is an organic compound with the molecular formula C6H5FN2. It is characterized by the presence of a fluorine atom attached to a phenyl ring and a hydrazine group. 4-FLUOROPHENYLHYDRAZINE is known for its reactivity and is commonly used as a building block in the synthesis of various organic molecules.

Uses

Used in Pharmaceutical Industry:
4-FLUOROPHENYLHYDRAZINE is used as a versatile reactant for the synthesis of various pharmaceutical compounds. Its unique structure allows it to participate in domino synthesis of indoles, which are important in the development of drugs targeting a wide range of medical conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-FLUOROPHENYLHYDRAZINE is used as a key intermediate in the production of various organic compounds. Its reactivity with terminal alkynes, facilitated by zinc-promoted hydrohydrazination, enables the efficient synthesis of complex molecules with potential applications in various industries.
Used in Research and Development:
4-FLUOROPHENYLHYDRAZINE is also utilized in research and development settings, where its unique properties and reactivity are harnessed to explore new synthetic pathways and develop novel compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C6H7FN2/c7-5-1-3-6(9-8)4-2-5/h1-4,9H,8H2

Upstream product

• 371-40-4 4-fluoroaniline 
• 137273-08-6 N'-(4-Fluoro-phenyl)-hydrazinecarboxylic acid 2,2,2-trichloro-ethyl ester 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 61161-10-2 N-(4-fluorophenyl)-nitramine 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 

Downstream Products

• 1549-74-2 maleic acid mono-(4-fluoro-phenylhydrazide) 
• 525-16-6 2-(4-fluoro-phenyl)-4-isopropylidene-5-methyl-2,4-dihydro-pyrazol-3-one 
• 368-22-9 salicylaldehyde-(4-fluoro-phenylhydrazone) 
• 7650-45-5 D-arabino-[2]hexosulose-bis-(4-fluoro-phenylhydrazone) 
• 576-16-9 5-fluorotryptamine 
• 399-72-4 5-fluoro-2-methyl-1H-indole 
• 125689-47-6 bis-(4-fluoro-phenyl)-antimony ⁽³⁺⁾; tris chloride 
• 137695-80-8 4-benzyl-2-(p-fluorophenyl)-3-hydroxy-2H-pyrazolo[4,3-c]isoquinolinium hydroxide 
• 462-06-6 fluorobenzene 
• 371-41-5 4-Fluorophenol 
• 220000-36-2 ethyl 2-benzoylamino-3-[(4-fluorophenyl)hydrazono]propanoate 

Relevant articles and documents

Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine

Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.

PROCESS FOR THE SYNTHESIS OF ARYL HYDRAZINES

The invention relates to a process for the synthesis of aryl hydrazinesof formula I or a salt thereof, which process comprises subjecting an arene of formula II to a coupling reaction with hydrazine or a derivative thereof, wherein the coupling reaction is conducted in the presence of a catalyst comprising palladium and a diphosphine ligand, wherein the phosphorus atoms are connected through two, three, four, or five atoms selected from car- bon, nitrogen, oxygen or iron, and in which the non-connecting phosphorus substituents are C1- C 10-alkyl or C3-C10-cycloalkyl, wherein the amount of Pd used is up to 0.5 mol-% relative to the amount of arene of formula II; and a base.

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.