13132-16-6

Basic information

• Product Name: 5-Benzyl-2-thiophenecarboxylic acid
• Synonyms: 5-Benzyl-2-thiophenecarboxylic acid;5-Benzyl-thiophene-2-carboxylic acid
• CAS NO: 13132-16-6
• Molecular Formula: C₁₂H₁₀O₂S
• Molecular Weight: 218.27
• Mol File: 13132-16-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Benzyl-2-thiophenecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Benzyl-2-thiophenecarboxylic acid(13132-16-6)
• EPA Substance Registry System: 5-Benzyl-2-thiophenecarboxylic acid(13132-16-6)

Safety Data

• Hazardous Substances Data: 13132-16-6(Hazardous Substances Data)

Upstream product

• 317335-12-9 1-(5-benzylthiophen-2-yl)ethanone 
• 527-72-0 2-thiophenylcarboxylic acid 
• 100-39-0 benzyl bromide 
• 929032-56-4 ethyl 5-benzylthiophene-2-carboxylate 
• 2810-04-0 Ethyl thiophene-2-carboxylate 
• 79505-01-4 5-(Phenylcarbonyl)thiophene-2-carboxylic acid 
• 59753-16-1 C₅H₂O₂S^(2-)*2Li⁽¹⁺⁾ 

Downstream Products

• 929032-56-4 ethyl 5-benzylthiophene-2-carboxylate 
• 929032-57-5 ethyl 5-(1,2-diphenylethyl)-2-thiophenecarboxylate 
• 86751-99-7 methyl 5-benzylthiophen-2-carboxylate 
• 5581-75-9 6-phenylhexanic acid 

Relevant articles and documents

Potent Thiophene Antagonists of Human Complement C3a Receptor with Anti-Inflammatory Activity

Structure-activity relationships for a series of small-molecule thiophenes resulted in potent and selective antagonism of human Complement C3a receptor. The compounds are about 100-fold more potent than the most reported antagonist SB290157. A new compound JR14a was among the most potent of the new antagonists in vitro, assessed by (a) inhibition of intracellular calcium release (IC50 10 nM) induced in human monocyte-derived macrophages by 100 nM C3a, (b) inhibition of β-hexosaminidase secretion (IC50 8 nM) from human LAD2 mast cells degranulated by 100 nM C3a, and (c) selectivity for human C3aR over C5aR. JR14a was metabolically stable in rat plasma and in rat liver microsomes and efficacious in rats when given orally to suppress rat paw inflammation, macrophage and mast cell activation, and histopathology induced by intraplantar paw administration of a C3aR agonist. Potent C3aR antagonists are now available for interrogating C3a receptor activation and suppressing C3aR-mediated inflammation in mammalian physiology and disease.

Generation and Synthetic Utility of Dianions Derived from Thiophencarboxylic Acids

Thiophen-2- and -3-carboxylic acid are rapidly and regioselectively metallated by lithium di-isopropylamide in tetrahydrofuran at -78 deg C.The resulting dianionic species react with a range of electrophiles to give the expected thiophencarboxylic acid homologues in good-to-excellent yields.

Formation and reactivity of dianions derived from 2- and 3-thiophencarboxylic acids

Dianions (3) and (6) can be generated in high yield from the corresponding thiophencarboxylic acids with lithium diisopropylamide and react with a number of representative electrophiles to give fair to good yields of 5-substituted-thiophen-2-carboxylic acids and 2-substituted thiophen-3-carboxylic acids respectively.