4-Hydroxylthiocoumarin

• CAS: 16854-67-4
• Catalog Number: ACM16854674
• Category: Main Products
• Molecular Weight: 178.21
• Molecular Formula: C9H6O2S
• Synonyms: 4-hydroxy-1-thiocoumarin; 4-hydroxythiocoumarun; 1-thio-4-hydroxycoumarin; 4-Hydroxythiocoumarin; 4-hydroxy-2H-1-benzothiopyran-2-one
• IUPAC Name: 2-hydroxythiochromen-4-one
• Boiling Point: 307.4ºC at 760 mmHg
• Flash Point: 139.7ºC
• Density: 1.478 g/cm³
• Exact Mass: 178.00900

Case Study

4-Hydroxy-1-Thiocoumarin for the Synthesis of 1-Thiocoumarin Derivatives

Mokrov, G. V., et al. Medicinal Chemistry Research, 2019, 28, 1901-1911.

Using the GABA pharmacophore and the corresponding heterocyclic moiety, a group of novel 4-GABA-3-nitrocoumarines, 1-thiocoumarines, quinolone-2-ones and their derivatives were designed as potential anticonvulsants. In the synthetic route, starting from 4-hydroxy-1-thiocoumarin (10) to produce 4-hydroxy-3-nitro-1-thiocoumarin (11) followed by 3-nitro-4-chloro-1-thiocoumarin (5) in sequential steps.
· Synthesis of 4-Hydroxy-3-nitro-1-thioumarin (11)
Added 19.8 mmol (1.4 ml) of 65% nitric acid together with 19.8 mmol (1.14 ml) of 96% sulfuric acid to an 80 ml glacial acetic acid suspension containing 18 mmol (3.21 g) of 4-hydroxy-1-thiocoumarin 10. For three hours the mixture remained stirred at room temperature. After filtering the precipitate, washed it twice using 10 ml of distilled water then dissolved it in hot toluene before filtering it through activated carbon and evaporating it to dryness resulting in 3.78 g of yellow powder as product with a yield of 92%.
· Synthesis of 3-Nitro-4-chloro-1-thiocoumarin (5)
0.373 ml of phosphoryl chloride (4 mmol) was combined with 2.5 ml of dimethylformamide and then stirred for 30 minutes. Then, 4 mmol (0.89 g) of 4-hydroxy-3-nitrothiocoumarin (11) in 9.6 ml of dimethylformamide was added to this solution, and the mixture was stirred for 2 hours. The process continued by adding 40 ml of cold water which caused the product to precipitate then the product was filtered and washed three times using 10 ml of distilled water before being recrystallized with 10 ml of ethanol which produced 0.85 g of dark yellow crystals with an 88% yield.

4-Hydroxy-1-Thiocoumarin for The Synthesis of Spiroindole-Linked Fused Pyrans

Mondal, Nurabul, et al. ChemistrySelect, 2024, 9(37), e202402549.

This work reported a visible light-mediated, catalyst-free, multicomponent reaction involving indigo, malononitrile or ethyl 2-cyanoacetate and cyclic 1,3-dicarbonyl compounds such as 4-hydroxy-1-thiocoumarin as starting materials to generate the corresponding spiroindole-linked fused pyrans.
Synthesis of Spirooxindole-Pyrans
· In a 4.0 mL glass vial equipped with a polypropylene screw cap and septum, 0.5 mmol (33 mg) of malononitrile (3a) and 0.5 mmol (74 mg) of isatin (2a) were dissolved in a 1:1 solution of ethanol and water (2 mL). To this mixture, 0.5 mmol of 4-hydroxy-1-thiocoumarin (5) was added. The resulting solution was continuously stirred under the light of two 30 W white LED bulbs. The reaction's progress was monitored using TLC with a solvent system of 50% ethyl acetate/hexane. Once the reaction was complete, the mixture was filtered through filter paper, and the crude product was purified by washing with ethanol, followed by drying in a hot air oven.
· The reaction of 4-hydroxy-1-thiocoumarin with malononitrile and indigo yielded the spiroindole-linked thiocoumarin-fused pyran 6a in a 91% yield. Employing this method, then synthesized a series of spirooxindoles 6b-6i by altering isatin derivatives while maintaining constant conditions. In each case, the three-component products 6b-6i were obtained in excellent yields ranging from 86% to 92%. Substituting ethyl-2-cyanoacetate 3b for malononitrile 3a resulted in the expected product 6j with a yield of 73%. Isatin derivatives featuring an electron-donating 5-OCH3 group and an electron-withdrawing 5-NO2 group produced products 6k and 6l with yields of 72% and 78%, respectively.

Custom Q&A

What is the molecular formula of 4-Hydroxylthiocoumarin?

The molecular formula of 4-Hydroxylthiocoumarin is C9H6O2S.

What is the molecular weight of 4-Hydroxylthiocoumarin?

The molecular weight of 4-Hydroxylthiocoumarin is 178.21 g/mol.

What are some synonyms for 4-Hydroxylthiocoumarin?

Some synonyms for 4-Hydroxylthiocoumarin are 4-hydroxy-2H-thiochromen-2-one, 2-hydroxythiochromen-4-one, and 2-Hydroxy-4H-1-benzothiopyran-4-one.

When was 4-Hydroxylthiocoumarin created?

4-Hydroxylthiocoumarin was created on July 8, 2005.

What is the InChIKey of 4-Hydroxylthiocoumarin?

The InChIKey of 4-Hydroxylthiocoumarin is OSIDMAJZERBPOJ-UHFFFAOYSA-N.

How many hydrogen bond donor counts does 4-Hydroxylthiocoumarin have?

4-Hydroxylthiocoumarin has 1 hydrogen bond donor count.

What is the topological polar surface area of 4-Hydroxylthiocoumarin?

The topological polar surface area of 4-Hydroxylthiocoumarin is 62.6 Å2.

How many defined atom stereocenter counts does 4-Hydroxylthiocoumarin have?

4-Hydroxylthiocoumarin has 0 defined atom stereocenter counts.

Is the compound of 4-Hydroxylthiocoumarin canonicalized?

Yes, the compound of 4-Hydroxylthiocoumarin is canonicalized.

What is the exact mass of 4-Hydroxylthiocoumarin?

The exact mass of 4-Hydroxylthiocoumarin is 178.00885060 g/mol.