Hangzhou Leap Chem Co., Ltd. is one of the most professional manufacturers and suppliers of thiophene-3-boronic acid丨cas 6165-69-1 in China. Welcome to wholesale bulk high quality chemical products at competitive price from our factory. If you have any enquiry about custom service, please feel free to email us.
Thiophene-3-boronic acid丨CAS 6165-69-1 Reliable Supplier
Thiophene-3-boronic acid (CAS 6165-69-1) is an organoboron compound featuring a thiophene ring substituted with a boronic acid group at the 3-position. Its heteroaromatic structure combines the chemical versatility of thiophene with the cross-coupling reactivity of the boronic acid functionality. This makes it a valuable building block in organic synthesis, particularly for constructing carbon–carbon bonds and introducing thiophene units into more complex molecular structures. As a heteroaryl boronic acid, it is especially useful in the preparation of functional aromatic compounds for pharmaceutical research, materials chemistry, and advanced chemical development.
Chemical Identifiers
| InChI | 1S/C4H5BO2S/c6-5(7)4-1-2-8-3-4/h1-3,6-7H |
| InChI Key | QNMBSXGYAQZCTN-UHFFFAOYSA-N |
| Smiles | OB(C1=CSC=C1)O |
| EC No. | 629-166-8 |
| MDL No. | MFCD00151851 |
| PubChem CID | 581760 |
Applications
Applications in Pharmaceutical and Agrochemical Intermediate Synthesis
Thiophene-3-boronic acid is used as a synthetic intermediate for introducing a thiophen-3-yl group into target molecules. Its boronic acid functionality makes it suitable for Suzuki–Miyaura cross-coupling reactions with aryl or heteroaryl halides, enabling the formation of biaryl and heterobiaryl structures. These transformations are valuable in medicinal chemistry, where thiophene-containing structures are frequently explored during the development of biologically active compounds and lead molecules. The reagent can support the preparation of substituted heteroaromatic intermediates for pharmaceutical and agrochemical research, allowing chemists to modify molecular frameworks and investigate structure–activity relationships.
Applications in Organic Synthesis and Cross-Coupling Reactions
One of the principal uses of Thiophene-3-boronic acid is Suzuki–Miyaura coupling, typically conducted with a suitable palladium catalyst and base. During the reaction, the thiophene-3-yl group is transferred to an organic coupling partner, forming a new carbon–carbon bond. This provides an efficient route to 3-substituted thiophenes and other conjugated heteroaromatic compounds. The reaction's functional-group compatibility and broad substrate scope make this building block useful for preparing structurally diverse molecules. It can also serve as a starting material for further functionalization, helping researchers develop multi-step synthetic routes to more complex thiophene derivatives.
Applications in Organic Electronics and Functional Materials
Thiophene derivatives are important structural components in organic electronic materials because their conjugated ring systems can contribute to electronic communication and molecular organization. Thiophene-3-boronic acid provides a practical route to incorporating thiophene units into extended aromatic structures through cross-coupling chemistry. The resulting compounds may be investigated as intermediates or building blocks for organic semiconductors, conjugated oligomers, functional polymers, and other materials used in organic electronic research. By coupling the thiophene ring with different aromatic or heteroaromatic partners, researchers can adjust molecular structure and explore the effects of substitution on optical, electronic, and physical properties.
Applications in Specialty Chemicals and Functional Molecules
In academic and industrial laboratories, Thiophene-3-boronic acid is useful for developing synthetic methods and preparing compound libraries containing thiophene motifs. Its defined substitution position offers a route to regioselectively functionalized products, supporting comparative studies of molecular structure and reactivity. It can also be used in reaction optimization, catalyst screening, and the preparation of reference intermediates for subsequent chemical transformations. These characteristics make it relevant to research involving heterocyclic chemistry, organometallic catalysis, and functional molecule development.
