Description

2-Bromo-4H,5H,6H-cyclopenta[b]thiophen-4-one (CAS: 1369353-77-4) is a high-purity brominated cyclopentathiophenone derivative with the molecular formula C₇H₅BrOS. This heterocyclic compound is characterized by its fused cyclopentene and thiophene rings, functionalized with a reactive bromine substituent and a ketone group. Its IUPAC name is 2-bromo-5,6-dihydrocyclopenta[b]thiophen-4-one, and it is supplied as a stable solid with rigorous quality control to ensure consistency for research applications. This compound is particularly valuable in organic synthesis, serving as a versatile intermediate for the development of pharmaceuticals, agrochemicals, and functional materials. Its unique structure enables participation in cross-coupling reactions, nucleophilic substitutions, and cyclization processes. Store in a cool, dry place under inert conditions to maintain optimal stability.

Properties

• CAS Number: 1369353-77-4
• Complexity: 171
• IUPAC Name: 2-bromo-5,6-dihydrocyclopenta[b]thiophen-4-one
• InChI: InChI=1S/C7H5BrOS/c8-7-3-4-5(9)1-2-6(4)10-7/h3H,1-2H2
• InChI Key: YSGWNYYXJIIWDG-UHFFFAOYSA-N
• Exact Mass: 215.92445
• Molecular Formula: C7H5BrOS
• Molecular Weight: 217.08
• SMILES: C1CC(=O)C2=C1SC(=C2)Br
• Topological: 45.3
• Monoisotopic Mass: 215.92445
• Synonyms: 2-bromo-4H,5H,6H-cyclopenta[b]thiophen-4-one, 1369353-77-4, 2-Bromo-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one, 2-bromo-5,6-dihydrocyclopenta[b]thiophen-4-one, SCHEMBL23042702, UEC35377, AKOS022689911, AT29694, CS-0433260, EN300-193501, Z1416172871

Application

2-Bromo-4H,5H,6H-cyclopenta[b]thiophen-4-one is a key building block in medicinal chemistry, particularly for the synthesis of thiophene-containing bioactive molecules. Its reactive bromine site facilitates palladium-catalyzed cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, to introduce diverse aryl or heteroaryl groups. Researchers also utilize this compound in the development of organic electronic materials, leveraging its conjugated system for optoelectronic applications. Additionally, it serves as a precursor for fused heterocycles in agrochemical research.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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