1346555-56-3 | 4-bromo-3-fluoro-1H-pyrazole

CAS:1346555-56-3 | 4-bromo-3-fluoro-1H-pyrazole,Description

4-Bromo-3-fluoro-1H-pyrazole is a pyrazole derivative. Pyrazoles are five-membered, π-excess heterocycles consisting of three carbon atoms and two adjacent nitrogen atoms. One nitrogen atom (N1) is pyrrole-like while the other (N2) is pyridine-like, allowing for both proton donor and acceptor properties.

Synthesis Analysis

Pyrazoles can be synthesized using various strategies such as multicomponent approach, dipolar cycloadditions, cyclocondensation of hydrazine with carbonyl system, using heterocyclic system and multicomponent approach. For instance, a silver-mediated [3 + 2] cycloaddition of N-isocyanoiminotriphenylphosphorane as “CNN” building block to terminal alkynes provides pyrazoles.

Molecular Structure Analysis

The structures of 4-chloro-1H-pyrazole and 4-fluoro-1H-pyrazole were published in 2021 and 2023, respectively. The bromo and chloro analogs are isostructural, forming trimeric H-bonding motifs, whereas the fluoro and iodo analogs form non-isostructural catemers.

Chemical Reactions Analysis

4-Bromopyrazole is reported to react with titanium tetrachloride to afford binary adducts. It’s also reported that 4-bromopyrazole inhibits the oxidative phosphorylation, the ATP -32 P exchange reaction, and energy dependent and independent calcium uptake.

Scientific Research Applications

• Synthesis of 1,4’-bipyrazoles

  • Field : Organic Chemistry 
  • Application : 4-Bromo-3-fluoro-1H-pyrazole is used as a starting material in the synthesis of 1,4’-bipyrazoles. Bipyrazoles are important compounds in organic chemistry due to their potential applications in various fields.
  • Method : The specific methods of synthesis can vary, but generally involve reactions with other organic compounds under controlled conditions.
  • Results : The outcome is the production of 1,4’-bipyrazoles, which can be used in further reactions or applications.

• Preparation of solid hexacoordinate complexes

  • Field : Coordination Chemistry
  • Application : 4-Bromo-3-fluoro-1H-pyrazole may be used in the preparation of solid hexacoordinate complexes by reaction with dimethyl- and divinyl-tindichloride.
  • Method : The specific methods of preparation can vary, but generally involve reactions with dimethyl- and divinyl-tindichloride.
  • Results : The outcome is the production of solid hexacoordinate complexes, which can be used in further reactions or applications.

• Synthesis of various pharmaceutical and biologically active compounds

  • Field : Medicinal Chemistry 
  • Application : 4-Bromo-3-fluoro-1H-pyrazole is also used in the synthesis of various pharmaceutical and biologically active compounds, including inhibitors.
  • Method : The specific methods of synthesis can vary, but generally involve reactions with other organic compounds under controlled conditions.
  • Results : The outcome is the production of various pharmaceutical and biologically active compounds, which can be used in further reactions or applications.

• Synthesis of Functionalized Pyrazoles

  • Field : Organic Chemistry
  • Application : 4-Bromo-3-fluoro-1H-pyrazole can be used in the synthesis of functionalized pyrazoles. These compounds have a wide range of applications in organic chemistry and medicinal chemistry.
  • Method : The specific methods of synthesis can vary, but generally involve reactions with other organic compounds under controlled conditions.
  • Results : The outcome is the production of functionalized pyrazoles, which can be used in further reactions or applications.

• Preparation of Polyurethanes

  • Field : Polymer Chemistry
  • Application : 4-Bromo-3-fluoro-1H-pyrazole can be used in the preparation of polyurethanes. Polyurethanes are widely used materials with applications in many areas, including coatings, adhesives, sealants, and elastomers.
  • Method : The specific methods of preparation can vary, but generally involve reactions with toluene diisocyanate (TDI) under controlled conditions.
  • Results : The outcome is the production of polyurethanes, which can be used in various applications.

• Synthesis of 1,3,4,5-Tetrasubstituted Pyrazoles

  • Field : Organic Chemistry
  • Application : 4-Bromo-3-fluoro-1H-pyrazole can be used in the synthesis of 1,3,4,5-tetrasubstituted pyrazoles. These compounds have potential applications in various fields, including medicinal chemistry.
  • Method : The specific methods of synthesis can vary, but generally involve reactions with other organic compounds under controlled conditions.
  • Results : The outcome is the production of 1,3,4,5-tetrasubstituted pyrazoles, which can be used in further reactions or applications.

• Synthesis of 1-Methyl-3-Pyridyl-5-Aryl Group

  • Field : Organic Chemistry
  • Application : 4-Bromo-3-fluoro-1H-pyrazole can be used in the synthesis of 1-methyl-3-pyridyl-5-aryl group. This group acts as a “turn on” probe for Cd 2+ ions in the presence of acetonitrile.
  • Method : The specific methods of synthesis can vary, but generally involve reactions with other organic compounds under controlled conditions.
  • Results : The outcome is the production of 1-methyl-3-pyridyl-5-aryl group, which can be used in further reactions or applications.

• Preparation of Transition Metal Chemosensors

  • Field : Analytical Chemistry
  • Application : 4-Bromo-3-fluoro-1H-pyrazole can be used in the preparation of transition metal chemosensors. These chemosensors are known for their remarkable photophysical, pH sensitivity, solvatochromic, ion detection, high quantum yields and nonlinear optical behavior.
  • Method : The specific methods of preparation can vary, but generally involve reactions with other compounds under controlled conditions.
  • Results : The outcome is the production of transition metal chemosensors, which can be used in environmental monitoring and biological imaging.

• Synthesis of 1,3,4,5-Tetrasubstituted Pyrazoles

  • Field : Organic Chemistry
  • Application : 4-Bromo-3-fluoro-1H-pyrazole can be used in the synthesis of 1,3,4,5-tetrasubstituted pyrazoles. These compounds have potential applications in various fields, including medicinal chemistry.
  • Method : The specific methods of synthesis can vary, but generally involve reactions with other organic compounds under controlled conditions.
  • Results : The outcome is the production of 1,3,4,5-tetrasubstituted pyrazoles, which can be used in further reactions or applications.

Safety And Hazards

4-Bromo-3-fluoro-1H-pyrazole is considered hazardous by the 2012 OSHA Hazard Communication Standard. It may cause harm if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation.

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