1360438-72-7 | 1,2-bis(chloranyl)-4-fluoranyl-3-nitro-benzene

CAS:1360438-72-7 | 1,2-bis(chloranyl)-4-fluoranyl-3-nitro-benzene,Description

1,2-Dichloro-4-fluoro-3-nitrobenzene is an organic compound with the molecular formula C6H2Cl2FNO2. It is used as an intermediate in the synthesis of agrochemicals.

Synthesis Analysis

The synthesis of 1,2-Dichloro-4-fluoro-3-nitrobenzene can be achieved through various methods. One such method involves the nitration of 1,2-dichlorobenzene, which mainly produces 1,2-dichloro-4-nitrobenzene, along with smaller amounts of the 3-nitro isomer. It can also be prepared by chlorination of 1-chloro-4-nitrobenzene.

Molecular Structure Analysis

The molecular structure of 1,2-Dichloro-4-fluoro-3-nitrobenzene is characterized by the presence of two chlorine atoms, one fluorine atom, and a nitro group attached to a benzene ring. The exact mass of the molecule is 208.9446619 g/mol.

Chemical Reactions Analysis

The chloride groups in 1,2-Dichloro-4-fluoro-3-nitrobenzene are reactive towards nucleophiles. For instance, potassium fluoride can react with this compound to produce 2-chloro-1-fluoro-4-nitrobenzene, an intermediate in the production of herbicides.

Physical And Chemical Properties Analysis

1,2-Dichloro-4-fluoro-3-nitrobenzene has a molecular weight of 209.99 g/mol. Other computed properties include a topological polar surface area of 45.8 Ų and a complexity of 187.

Scientific Research Applications

1. Synthesis of Agrochemicals and Pharmaceuticals

• Application Summary: 1,2-Dichloro-4-fluoro-3-nitrobenzene is used as an intermediate in the synthesis of trifluoromethylpyridines (TFMP), which are key structural motifs in active agrochemical and pharmaceutical ingredients.
• Methods of Application: The compound can be prepared by the nitration of 1,2-dichlorobenzene, which mainly produces 1,2-dichloro-4-nitrobenzene, along with smaller amounts of the 3-nitro isomer. It can also be prepared by the chlorination of 1-chloro-4-nitrobenzene. One of the chlorides is reactive toward nucleophiles. For example, potassium fluoride gives 2-chloro-1-fluoro-4-nitrobenzene, an intermediate in the production of herbicides. With ammonia, one obtains 2-chloro-4-nitroaniline, a precursor to diazo dyes.
• Results or Outcomes: The major use of TFMP derivatives is in the protection of crops from pests. More than 20 new TFMP-containing agrochemicals have acquired ISO common names. Several TFMP derivatives are also used in the pharmaceutical and veterinary industries; five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials.

2. Detection and Determination of Pyridine Compounds

• Application Summary: 1,2-Dichloro-4-fluoro-5-Nitrobenzene (DFNB) is used as a reagent for the detection and determination of nicotinic acid, nicotinamide, and other pyridine compounds.
• Methods of Application: The specific methods of application would depend on the exact experimental setup and the specific pyridine compounds being analyzed. Typically, the compound would be used in a colorimetric or spectrophotometric assay.
• Results or Outcomes: The results would depend on the specific experiment, but generally, this application allows for the detection and quantification of pyridine compounds.

3. Synthesis of Ciprofloxacin

• Application Summary: 1,2-Dichloro-4-nitrobenzene is used as an organic intermediate for the synthetic preparation of ciprofloxacin, a commonly used antibiotic.
• Methods of Application: The specific synthetic pathway would depend on the exact experimental conditions, but generally, the compound would be used in a multi-step synthesis involving various other reagents and catalysts.
• Results or Outcomes: The result of this application is the synthesis of ciprofloxacin, a widely used antibiotic.

4. Combinatorial Solid-Phase Synthesis of Bis-Heterocyclic Compounds

• Application Summary: 1,2-Dichloro-4-fluoro-5-nitrobenzene may be used in the combinatorial solid-phase synthesis of bis-heterocyclic compounds.
• Methods of Application: The compound is used in a solid-phase synthesis, a method that allows for the rapid synthesis of a large number of different compounds in parallel.
• Results or Outcomes: The result of this application is the synthesis of a library of bis-heterocyclic compounds, which can be used for various purposes such as drug discovery.

5. Electrophilic Aromatic Substitution

• Application Summary: 1,2-Dichloro-4-fluoro-3-nitrobenzene is used in electrophilic aromatic substitution reactions. These reactions are fundamental in organic chemistry and are used to introduce functional groups onto aromatic rings.
• Methods of Application: The specific methods of application would depend on the exact experimental setup and the specific functional groups being introduced. Typically, the compound would be used in a reaction with an electrophile, which would replace one of the hydrogen atoms on the aromatic ring.
• Results or Outcomes: The results would depend on the specific experiment, but generally, this application allows for the introduction of various functional groups onto the aromatic ring.

6. Synthesis of Dyes

• Application Summary: 1,2-Dichloro-4-fluoro-3-nitrobenzene can be used in the synthesis of diazo dyes.
• Methods of Application: The compound can react with ammonia to form 2-chloro-4-nitroaniline, a precursor to diazo dyes.
• Results or Outcomes: The result of this application is the synthesis of various diazo dyes, which are used for coloring textiles, leather, and paper.

Safety And Hazards

1,2-Dichloro-4-fluoro-3-nitrobenzene is toxic to aquatic organisms and may cause long-term effects in the aquatic environment. It is strongly advised not to let the chemical enter into the environment.

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