1214383-87-5 | 3-Bromo-6-hydroxy-2-(trifluoromethyl)pyridine

CAS:1214383-87-5 | 3-Bromo-6-hydroxy-2-(trifluoromethyl)pyridine,Description

3-Bromo-6-hydroxy-2-(trifluoromethyl)pyridine is a chemical compound with the CAS Number: 1214383-87-5. It has a molecular weight of 242.

Synthesis Analysis

The synthesis of substituted pyridines with diverse functional groups has been reported via the remodeling of (Aza)indole/Benzofuran skeletons. A ring cleavage methodology reaction for the synthesis of 2-alkyl/aryl 3-electron-withdrawing groups (esters, sulfones, and phosphonates) 5-aminoaryl/phenol pyridines via the remodeling of 3-formyl (aza)indoles/benzofurans has been reported.

Molecular Structure Analysis

The molecular formula of 3-Bromo-6-hydroxy-2-(trifluoromethyl)pyridine is C6H3BrF3NO. The InChI code is 1S/C6H3BrF3NO/c7-3-1-2-4 (12)11-5 (3)6 (8,9)10/h1-2H, (H,11,12).

Chemical Reactions Analysis

The major use of trifluoromethylpyridine (TFMP) derivatives is in the protection of crops from pests. More than 20 new TFMP-containing agrochemicals have acquired ISO common names.

Physical And Chemical Properties Analysis

The molecular weight of 3-Bromo-6-hydroxy-2-(trifluoromethyl)pyridine is 241.99 g/mol. It has a Hydrogen Bond Donor Count of 1 and a Hydrogen Bond Acceptor Count of 4. The compound has a Rotatable Bond Count of 0. The Exact Mass is 240.93501 g/moland the Monoisotopic Mass is also 240.93501 g/mol. The Topological Polar Surface Area is 29.1 Ų.

Scientific Research Applications

• Pharmaceutical Industry

  • Summary of Application : Several TFMP derivatives are used in the pharmaceutical industry. Five pharmaceutical products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials.
  • Methods of Application : The methods of application in the pharmaceutical industry can vary greatly depending on the specific drug and its intended use.
  • Results or Outcomes : The biological activities of TFMP derivatives are thought to be due to the combination of the unique physicochemical properties of the fluorine atom and the unique characteristics of the pyridine moiety.

• Synthesis of Crop-Protection Products

  • Summary of Application : Among TFMP derivatives, 2,3-dichloro-5-(trifluoromethyl)pyridine (2,3,5-DCTF), which is used as a chemical intermediate for the synthesis of several crop-protection products, is in the highest demand.
  • Methods of Application : 2,3,5-DCTF can be obtained by direct chlorination and fluorination of 3-picoline and followed by aromatic nuclear chlorination of the pyridine ring.
  • Results or Outcomes : Various methods of synthesizing 2,3,5-DCTF have been reported.

• Synthesis of Metal-Organic Frameworks (MOFs)

  • Summary of Application : TFMP derivatives can be used in the synthesis of metal-organic frameworks (MOFs), which are compounds consisting of metal ions or clusters coordinated to organic ligands.
  • Methods of Application : The specific methods of application can vary depending on the specific MOF being synthesized.
  • Results or Outcomes : The resulting MOFs can have a wide range of applications, including gas storage, separation, and catalysis.

• Preparation of (Trifluoromethyl)pyridyllithiums

  • Summary of Application : TFMP derivatives can be used in the preparation of (trifluoromethyl)pyridyllithiums via metalation reaction.
  • Methods of Application : The specific methods of application can vary depending on the specific (trifluoromethyl)pyridyllithium being synthesized.
  • Results or Outcomes : The resulting (trifluoromethyl)pyridyllithiums can be used as intermediates in various organic reactions.

• Synthesis of Methiodide Salts

  • Summary of Application : TFMP derivatives can be used in the synthesis of methiodide salts.
  • Methods of Application : The specific methods of application can vary depending on the specific methiodide salt being synthesized.
  • Results or Outcomes : The resulting methiodide salts can have various applications in organic synthesis.

• Development of Agrochemical and Pharmaceutical Compounds

  • Summary of Application : TFMP and its intermediates have gained a fundamental role as key structural ingredients for the development of many agrochemical and pharmaceutical compounds.
  • Methods of Application : The methods of application in the agrochemical and pharmaceutical industries can vary greatly depending on the specific compound and its intended use.
  • Results or Outcomes : The demand for TFMP derivatives has been increasing steadily in the last 30 years.

• Manufacturing TFMPs to Meet a Steady Growth in Demand

  • Summary of Application : The demand for TFMP derivatives has been increasing steadily in the last 30 years.
  • Methods of Application : TFMP intermediates are generally manufactured via two main methods: one involving an exchange between chlorine and fluorine atoms using trichloromethyl-pyridine, and the other relies on the assembly of pyridine from a trifluoromethyl-containing building block.
  • Results or Outcomes : Whether TFMP intermediates are manufactured using the direct fluorination method or the building-block method, depends largely on the identity of the desired target compound.

• Organic Synthesis Intermediate

  • Summary of Application : “2-Hydroxy-6-trifluoromethylpyridine” is a common organic synthesis intermediate.
  • Methods of Application : It often participates in subsequent transformations in its enol form, but it can also obtain a methoxy product with the pyridine ring structure preserved under the protection of iodomethane.
  • Results or Outcomes : The methoxy product can be used as an intermediate in various organic reactions.

Safety And Hazards

The compound has been assigned the GHS07 pictogram and the signal word "Warning". Hazard statements include H302, H315, H319, H335. Precautionary statements include P261, P271, P280, P302, P304, P305, P313, P332, P337, P338, P340, P351, P352.

Future Directions

The development of organic compounds containing fluorine has led to many recent advances in the agrochemical, pharmaceutical, and functional materials fields. It is expected that many novel applications of TFMP will be discovered in the future.

More Information