2-Thiophenecarbonyl chloride
[CAS# 5271-67-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic acid halide
• Name: 2-Thiophenecarbonyl chloride
• Synonyms: Thiophene-2-carbonyl chloride
• Molecular Formula: C₅H₃ClOS
• Molecular Weight: 146.59
• CAS Registry Number: 5271-67-0
• EC Number: 226-092-4
• SMILES: C1=CSC(=C1)C(=O)Cl

Properties

• Density: 1.372 g/mL (Expl.)
• Boiling point: 206-208 ºC (Expl.)
• Refractive index: 1.59 (Expl.)
• Flash point: 90 ºC (Expl.)

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - single exposure	STOT SE	1	H335
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	4	H302

• Transport Information: UN 3265

Discovory and Applicatios

2-Thiophenecarbonyl chloride (C7H5ClO) is an organic compound that consists of a thiophene ring attached to a carbonyl chloride group. It is an important intermediate in the synthesis of various chemical compounds and has broad applications in organic synthesis and industrial chemistry. The discovery of 2-thiophenecarbonyl chloride was part of ongoing efforts in the mid-20th century to explore the reactivity and potential of thiophene derivatives, particularly those with electrophilic functional groups like acyl chlorides. Its ability to form derivatives with various functional groups has made it valuable in both academic research and industrial applications.

The discovery of 2-thiophenecarbonyl chloride can be traced back to the development of techniques for the chlorination of thiophene derivatives. Researchers were particularly interested in how functional groups could be introduced onto the thiophene ring, as these derivatives could exhibit enhanced reactivity and serve as versatile building blocks for more complex molecules. Over time, 2-thiophenecarbonyl chloride was recognized as an important reagent for introducing a carbonyl group to thiophene-based molecules, and its applications have been expanded into diverse areas of chemical research.

One of the primary applications of 2-thiophenecarbonyl chloride is in organic synthesis, where it is used as an acylating agent. The carbonyl chloride group is highly electrophilic, making it reactive toward nucleophilic compounds. This property allows it to form carbon-carbon bonds with a wide variety of nucleophiles, such as alcohols, amines, and other thiophene derivatives. The resulting products are valuable intermediates for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals.

In addition to its role as an acylating agent, 2-thiophenecarbonyl chloride has been employed in the synthesis of thiophene-based heterocycles. These heterocyclic compounds are of significant interest due to their diverse biological activities, including antimicrobial, anticancer, and anti-inflammatory properties. By introducing the carbonyl group into the thiophene ring structure, 2-thiophenecarbonyl chloride enables the creation of molecules with improved solubility, bioavailability, and biological efficacy. This has led to its use in the development of new drug candidates and agrochemicals.

The reactivity of 2-thiophenecarbonyl chloride also makes it a useful tool in materials science. Thiophene derivatives, including those modified with carbonyl groups, are often used in the preparation of conductive polymers, which have applications in electronics, sensors, and energy storage devices. These conductive materials benefit from the unique electronic properties of the thiophene ring, and the incorporation of functional groups like carbonyl enhances their performance in various applications, including organic photovoltaics and organic light-emitting diodes (OLEDs).

In the pharmaceutical industry, 2-thiophenecarbonyl chloride is used to synthesize various bioactive molecules. It is particularly valuable in the synthesis of compounds with potential anticancer, antimicrobial, and anti-inflammatory properties. The carbonyl chloride group allows for the introduction of additional functional groups that can modulate the activity of the resulting compounds, making them more potent or selective for specific biological targets. This has made 2-thiophenecarbonyl chloride a key reagent in the development of therapeutic agents.

In summary, 2-thiophenecarbonyl chloride is an important chemical substance that plays a key role in organic synthesis, materials science, and pharmaceutical development. Its discovery and application have enabled the creation of a wide range of thiophene-based compounds with enhanced reactivity and biological activity. From its use as an acylating agent in the synthesis of complex organic molecules to its role in the development of new drugs and materials, 2-thiophenecarbonyl chloride continues to be a valuable tool in both academic and industrial chemistry.