Acetic acid, 2-(4-mercapto-2-methylphenoxy)-, ethyl ester
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Product Description
Acetic acid, 2-(4-mercapto-2-methylphenoxy)-, ethyl ester is a complex organic compound that can be described as an ethyl acetate derivative with a 4-mercapto-2-methylphenoxy group attached to the 2-position of the acetate group. Structurally, it is known as ethyl 2-(4-mercapto-2-methylphenoxy)acetate. This molecule contains several key functional groups, including a highly nucleophilic thiol group that readily reacts with electrophiles and is prone to oxidation, forming disulfide bonds. The ester group can undergo hydrolysis under acidic or alkaline conditions, while the aryl ether bond is relatively stable. The compound features a benzene ring with a methyl group at position 2 and a mercapto group at position 4, connected to an ethyl ester moiety. It is likely a synthetic intermediate or potential impurity in the production of seladelpar, a PPARδ agonist used for treating liver diseases.
Uses
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Pharmaceutical Intermediates: The thiol and ester groups make it useful in drug synthesis, particularly as a synthetic intermediate or potential impurity in the production of seladelpar (MBX-8025), a PPARδ agonist used for treating liver diseases like primary biliary cholangitis.
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Polymer Chemistry: May act as a crosslinking agent or modifier in resins.
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Coordination Chemistry: The thiol group can bind to metals (e.g., gold, silver) for nanomaterials.
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Chemical Intermediate: Listed by chemical suppliers for use as an intermediate in the chemical industry, referenced in patent literature in the synthesis of more complex molecules.
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Impurity Profiling: Relevant in impurity profiling, analysis, or purification development in pharmaceutical manufacturing.
Potential Applications
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Materials Chemistry: Useful in surface functionalization or as a ligand in organometallic chemistry.
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Drug Scaffolding: Potential use as a ligand or drug scaffold due to its aromatic character and functional groups.
Cautions and Limitations
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Specialized Use: Likely specialized/niche/research-scale rather than large-scale industrial use.
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Stability Issues: Thiol compounds are often sensitive to oxidation and have stability issues unless stabilized.
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Patent Context: Often mentioned as a precursor rather than a final active ingredient in patent claims.
Chemical Information
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Molecular Formula: C₁₁H₁₄O₃S
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Molecular Weight: 226.29 g/mol
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CAS Number: 343322-82-7
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IUPAC Name: Ethyl 2-(2-methyl-4-sulfanylphenoxy)acetate
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SMILES Notation: CCOC(=O)COC1=C(C=C(C=C1)S)C
Structure and Classification
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Core Structure: Contains a phenoxy group (C₆H₄O) linked to an acetate ester (CH₃COO) via a two-carbon spacer.
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Substituents:
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Methyl group (-CH₃) at the 2-position of the benzene ring.
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Thiol group (-SH) at the 4-position of the benzene ring.
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Ethyl ester (-OCOCH₂CH₃) at the acetate terminus.
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Key Features:
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Phenoxy Ether Linkage: The oxygen in the phenoxy group connects the aromatic ring to the acetate chain.
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Mercapto Group: The -SH group is reactive, often participating in thiol-disulfide exchange or metal coordination.
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Ester Functionality: The ethyl ester is hydrolyzable under acidic or basic conditions, releasing ethanol and the free acid.
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Physical Properties
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State: Liquid
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Boiling Point: Not specified
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Melting Point: Not specified
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Solubility: Not specified
Safety Information
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Odor: Strong, unpleasant smell due to the thiol group.
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Irritation: Potential skin and eye irritation; handle with gloves and in a fume hood.
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Storage: Handle with care in a lab setting; standard precautions for organic esters and thiols apply (e.g., avoid inhalation, use ventilation).