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 146.14 and its IUPAC name is 3-fluoro-2-thiophenecarboxylic acid . It is a solid substance and 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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