386704-12-7 | 6-(TRIFLUOROMETHYL)PYRIDINE-3-CARBOXALDEHYDE

CAS:386704-12-7 | 6-(TRIFLUOROMETHYL)PYRIDINE-3-CARBOXALDEHYDE,Description

6-(Trifluoromethyl)pyridine-3-carboxaldehyde, also known as 6-(Trifluoromethyl)nicotinaldehyde, is a laboratory chemical . It has the empirical formula C7H4F3NO and a molecular weight of 175.11 .

Synthesis Analysis

The synthesis of 6-(Trifluoromethyl)pyridine-3-carboxaldehyde involves several steps . Under nitrogen protection, 1 eq of 2-trifluoromethyl-5-bromopyridine is added to a reaction vessel and dissolved with an organic solvent. The temperature is controlled to be between -20 and 10°C, and a stabilizer is added. Then, a butyl lithium n-hexane solution is added dropwise while stirring. After adding dimethyl formamide, the temperature is allowed to rise naturally, and the mixture is stirred overnight. The crude product is then purified by recrystallization .

Molecular Structure Analysis

The molecular structure of 6-(Trifluoromethyl)pyridine-3-carboxaldehyde can be represented by the SMILES string [H]C(=O)c1ccc(nc1)C(F)(F)F . The InChI key for this compound is MRPAGRCGPAXOGS-UHFFFAOYSA-N .

Chemical Reactions Analysis

6-(Trifluoromethyl)pyridine-3-carboxaldehyde has been used in the synthesis of a series of potent and selective inhibitors of aldosterone synthase (CYP11B2). The key synthetic step in this process was a Wittig reaction using various heterocyclic aldehydes .

Physical And Chemical Properties Analysis

6-(Trifluoromethyl)pyridine-3-carboxaldehyde is a solid with a melting point of 52-56°C . It should be stored at a temperature of 2-8°C .

Scientific Research Applications

• Agrochemical Industry

  • Summary of Application : TFMP derivatives are widely used in the agrochemical industry for the protection of crops from pests . The major use of TFMP derivatives is in the protection of crops from pests .
  • Methods of Application : The synthesis of TFMP derivatives is generally achieved via two main methods: one involving an exchange between chlorine and fluorine atoms using trichloromethyl-pyridine. The second method relies on the assembly of pyridine from a trifluoromethyl-containing building block .
  • Results or Outcomes : More than 20 new TFMP-containing agrochemicals have acquired ISO common names .

• Pharmaceutical Industry

  • Summary of Application : Several TFMP derivatives are 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 .
  • Methods of Application : Similar to the agrochemical industry, the synthesis of TFMP derivatives in the pharmaceutical industry is achieved via the methods mentioned above .
  • 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 .

• Manufacturing of Crop-Protection Products

  • Summary of Application : 2,3-dichloro-5-(trifluoromethyl) pyridine (2,3,5-DCTF), a derivative of TFMP, is used in the production of several crop-protection products .
  • 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 : Of all the TFMP derivatives, 2,3,5-DCTF is in highest demand for the production of crop-protection products .

• Functional Materials

  • Summary of Application : Many recent advances in the functional materials fields have been made possible by the development of organic compounds containing fluorine .
  • Methods of Application : The synthesis of TFMP derivatives in the functional materials industry is achieved via the methods mentioned above .
  • Results or Outcomes : As the number of applications for these compounds continues to grow, the development of fluorinated organic chemicals is becoming an increasingly important research topic .

• Pesticides

  • 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 . In the crop protection industry, more than 50% of the pesticides launched in the last two decades have been fluorinated .
  • Methods of Application : The researchers explain that this is generally achieved via two main methods: one involving an exchange between chlorine and fluorine atoms using trichloromethyl-pyridine. The second method relies on the assembly of pyridine from a trifluoromethyl-containing building block .
  • Results or Outcomes : Around 40% of all fluorine-containing pesticides currently on the market contain a trifluoromethyl group, making these compounds an important subgroup of fluorinated compounds .

• Development of Novel Biological Properties

  • Summary of Application : To develop compounds with unique biological properties, hydrogen is commonly replaced with fluorine .
  • Methods of Application : The synthesis of TFMP derivatives in the development of novel biological properties is achieved via the methods mentioned above .
  • 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 .

Safety And Hazards

This chemical is considered hazardous according to the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It is toxic if swallowed, causes skin irritation, serious eye irritation, may cause an allergic skin reaction, and may cause respiratory irritation . It should be handled with appropriate personal protective equipment, including a dust mask type N95 (US), eyeshields, and gloves .

Future Directions

While specific future directions for 6-(Trifluoromethyl)pyridine-3-carboxaldehyde are not provided in the search results, its use in the synthesis of potential Alzheimer’s treatment agents suggests it may have future applications in medicinal chemistry .

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