4-mercaptophenylaceti cacid
$250.00
CAS No.: 39161-84-7
Catalog No.: 194987
Purity: 95%
MF: C8H8O2S
MW: 168.217
Storage: 2-8 degree Celsius
SMILES: SC1=CC=C(C=C1)CC(=O)O
Catalog No.: 194987
Purity: 95%
MF: C8H8O2S
MW: 168.217
Storage: 2-8 degree Celsius
SMILES: SC1=CC=C(C=C1)CC(=O)O
4-mercaptophenylaceti cacid; CAS No.: 39161-84-7; 4-mercaptophenylacetic acid. PROPERTIES: 4-mercaptophenylacetic acid appears as white to off-white powder with molecular formula C8H8O2S. It has a melting point of approximately 135-137 C and is soluble in water ( 200 mg/mL at 25 C) and common polar solvents. The compound is hygroscopic and prone to oxidation upon exposure to air and light. Recommended storage involves keeping in nitrogen-purged containers with antioxidants at temperatures below -20 C. From a safety perspective, this compound presents moderate acute toxicity (LD50 ~280 mg/kg) and poses severe skin and eye irritation hazards. It is classified as harmful if inhaled or swallowed and may cause respiratory tract irritation. Handling requires use of chemical-resistant gloves, acid-resistant aprons, and powered air-purifying respirators. APPLICATIONS: In pharmaceutical synthesis, 4-mercaptophenylacetic acid serves as a key intermediate for producing certain ACE inhibitors. The thiophenyl group provides critical interactions with the enzyme active site while the carboxylic acid group forms the essential zinc-binding motif, resulting in compounds with IC50 values as low as 4 nM (Journal of Medicinal Chemistry). In chemical biology, the compound functions as a building block for creating glutathione mimetics. The thiolic group participates in Michael addition reactions with ϫ, -unsaturated carbonyls, enabling study of redox signaling pathways with reaction rates exceeding 10^3 M^-1s^-1 (Biochemistry). In materials science, the compound is utilized as a capping agent for quantum dot synthesis. The thiol group binds to semiconductor nanoparticle surfaces while the carboxylic acid group provides aqueous solubility and functionalization sites, resulting in quantum dots with photoluminescence quantum yields up to 75% (Nano Letters). In the field of analytical chemistry, the compound acts as a derivatizing agent for improving detection of thiols in biological samples. Upon reaction with free thiols, the resulting disulfide bonds enhance electrospray ionization efficiency, allowing quantification with LODs as low as 100 fM (Analytical Biochemistry).
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