5-Acetylthiophene-2-carboxylic acid
[CAS# 4066-41-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: 5-Acetylthiophene-2-carboxylic acid
• Synonyms: 5-Acetyl-2-thiophenecarboxylic acid
• Molecular Formula: C₇H₆O₃S
• Molecular Weight: 170.19
• CAS Registry Number: 4066-41-5
• EC Number: 609-857-0
• SMILES: CC(=O)C1=CC=C(S1)C(=O)O

Properties

• Density: 1.383
• Melting point: 204-205 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

5-Acetylthiophene-2-carboxylic acid is an important compound in organic chemistry known for its unique structure and diverse applications. The molecule features a thiophene ring substituted with an acetyl group and a carboxylic acid, which gives it unique chemical properties that make it valuable in various fields.

The compound was first synthesized in the early 20th century when researchers were exploring the reactivity and derivatives of thiophene. The interest in thiophene and its derivatives stems from their importance in the development of dyes, pharmaceuticals, and agrochemicals. The synthesis of 5-acetylthiophene-2-carboxylic acid involves the acetylation of thiophene-2-carboxylic acid to form this functionalized derivative. Its discovery has opened up new avenues for research, especially in the synthesis of complex organic molecules.

5-Acetylthiophene-2-carboxylic acid is a key building block in organic synthesis. Its functional groups allow for further derivatization and can be used to create more complex molecules. Chemists have utilized this compound in various synthetic pathways to develop new drugs and agrochemicals.

The compound shows potential in medicinal chemistry and its biological activity is being explored. Its structure may contribute to pharmacological properties, thereby studying its efficacy against various diseases. Therefore, it can serve as a lead compound in drug discovery efforts.

Due to its unique thiophene structure, 5-acetylthiophene-2-carboxylic acid is also used in dyes and pigments. The thiophene ring can impart desirable color properties, making it suitable for use in the textile and coating industries.

In materials science, the properties of this compound are studied for potential applications in the manufacture of conductive polymers and organic electronic devices. Incorporating thiophene derivatives into materials can enhance their electrical properties, paving the way for innovative technological applications.

References

2021. Photo-induced deep aerobic oxidation of alkyl aromatics. Science China Chemistry, 64(6).
DOI: 10.1007/s11426-021-1032-7

2011. Enthalpy of formation of thiophene derivatives. Chemistry of Heterocyclic Compounds, 47(2).
DOI: 10.1007/s10593-011-0668-5

1984. Thienyl-2-acetic acid as a synthetic agent for the preparation of macrocyclic compounds containing a thiophene ring. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 33(1).
DOI: 10.1007/bf00956249