32431-84-8 | 2-Thiophenecarboxylic acid, 3-fluoro-

CAS:32431-84-8 | 2-Thiophenecarboxylic acid, 3-fluoro-,Description

3-Fluorothiophene-2-carboxylic acid is a chemical compound with the CAS Number: 32431-84-8. It has a molecular weight of 146.14and its IUPAC name is 3-fluoro-2-thiophenecarboxylic acid. It is a solid substanceand is usually stored in a dark place, sealed in dry, at 2-8°C.

Synthesis Analysis

The synthesis of 3-Fluorothiophene-2-carboxylic acid involves a reaction with n-butyllithium in tetrahydrofuran and hexane at -78℃ for 0.5 hours, followed by a reaction with N-fluorobis(benzenesulfon)imide in tetrahydrofuran and hexane at -78 - 20℃ for 10 hours.

Molecular Structure Analysis

The molecular structure of 3-Fluorothiophene-2-carboxylic acid is represented by the formula C5H3FO2S.

Physical And Chemical Properties Analysis

3-Fluorothiophene-2-carboxylic acid is a solid substance. It is usually stored in a dark place, sealed in dry, at 2-8°C. .

Scientific Research Applications

Thiophene-based analogs, including 3-Fluorothiophene-2-carboxylic acid, have been of interest to a growing number of scientists as a potential class of biologically active compounds. They play a vital role for medicinal chemists to improve advanced compounds with a variety of biological effects.

Thiophene and its derivatives are essential heterocyclic compounds and show a variety of properties and applications. They are utilized in industrial chemistry and material science as corrosion inhibitors. Thiophene-mediated molecules have a prominent role in the advancement of organic semiconductors, organic field-effect transistors (OFETs), and in the fabrication of organic light-emitting diodes (OLEDs).

Molecules with the thiophene ring system exhibit many pharmacological properties such as anticancer, anti-inflammatory, antimicrobial, antihypertensive, and anti-atherosclerotic properties.

For example, suprofen has a 2-substituted thiophene framework and is known as a nonsteroidal anti-inflammatory drug and articaine as 2,3,4-trisubstituent thiophene (3-n-propylamino-α-propionylamino-2-carbomethoxy-4-methyl-thiophene hydrochloride), is used as a voltage-gated sodium channel blocker and dental anesthetic in Europe.

The synthesis of thiophene derivatives involves various methods including the Gewald, Paal–Knorr, Fiesselmann, and Hinsberg synthesis. The Gewald is a condensation reaction between sulfur, an α-methylene carbonyl compound, and an α-cyano ester, which makes aminothiophene derivatives. The Paal–Knorr reaction is known as the condensation of 1,4-dicarbonyl compounds with phosphorus pentasulfide (P 4 S 10) as sulfurizing agents.

• Organic Semiconductors

  • Fluorinated thiophene derivatives are widely used as soluble semiconductors. These compounds have shown promise in the development of organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs).

• Pharmaceutical Applications

  • Some fluorinated thiophene derivatives represent potent selective class II histone deacetylase (HDAC) inhibitors, which are used in cancer treatment. Others act as agonists of sphingosine-1-phosphate (S1P) receptors, which are involved in immune system regulation.

• Fungicidal Properties

  • Certain fluorinated thiophene derivatives reveal fungicidal properties, making them useful in the development of new antifungal treatments.

• Anti-inflammatory and Immunoregulatory Activity

  • Some fluorinated thiophene derivatives have shown anti-inflammatory and immunoregulatory activity, suggesting potential applications in the treatment of inflammatory diseases and disorders of the immune system.

• Photochromic Compounds

  • Thiophene-substituted perfluorocyclopentenes are being investigated as thermally irreversible photochromic compounds having a high resistance to fatigue. These materials could have applications in optical data storage and other areas.

• Liquid Crystals

  • Fluorinated thiophene derivatives are used in the development of liquid crystals, which have applications in display technologies and other areas.

• Synthesis of Fluorothiophenes

  • The synthesis of fluorothiophenes involves various methods including direct fluorination of thiophene with molecular fluorine (F 2), which is not a selective process due to the extreme reactivity of molecular fluorine. For example, the reaction of thiophene 1 with fluorine at −63 °C (5 % F 2 in He) gave a mixture of 2- and 3-fluorothiophene 2 and 3 in a 2:1 ratio.
  • Another method involves the treatment of 2- (thiophene-2-yl)acetonitrile 4 with perchloryl fluoride (FClO 3) in N,N-dimethylformamide in the presence of sodium ethoxide.

• Preparation of Thiophenes with a Fluorine Atom

  • Methods for the preparation of thiophenes with a fluorine atom in the 2- and 3-position, and polyfluorothiophenes have been described. These methods are classified into functionalization of the thiophene ring and heterocyclizations.

• Synthesis of 2-Fluorobenzo[b]thiophene

  • The synthesis of 2-fluorobenzo[b]thiophene involves the successive reaction of β,β-difluoro- o -methylsulfinylstyrene 63 first with trifluoroacetic anhydride and triethylamine in dichloromethane and then with potassium carbonate.

• Transformations of Iodonium Salts

  • A more useful approach to fluorothiophenes is based on transformations of iodonium salts. 2-Thienyliodoniym salts, for example dithiophen-2-yliodonium hexafluorophosphate 39, afford 2-fluorothiophene 2 (37 %) and thiophene 1 (20 %) after treatment with potassium fluoride and heating at 172–175 °C.

• Chemical Synthesis

  • 3-Fluorothiophene-2-carboxylic acid is used in chemical synthesis. It is a white to yellow powder or crystals stored at refrigerator temperature.

• Material Science

  • Fluorinated thiophene derivatives are used in material science as they are widely used as soluble semiconductors, polymers, blue light emitting materials, and liquid crystals.

Safety And Hazards

The safety information for 3-Fluorothiophene-2-carboxylic acid indicates that it has the GHS07 pictogram and the signal word "Warning". The hazard statements include H315, H319, and H335. The precautionary statements include P261, P305, P338, and P351.

Relevant Papers The relevant papers for 3-Fluorothiophene-2-carboxylic acid are not explicitly mentioned in the search results.

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