39088-65-8

Basic information

• Product Name: 4-(mercaptomethyl)benzoic acid
• Synonyms: 4-(sulfanylmethyl)benzoate
• CAS NO: 39088-65-8
• Molecular Formula: C₈H₈O₂S
• Molecular Weight: 168.2129
• EINECS: 254-286-9
• Mol File: 39088-65-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 176 °C
• Boiling Point: 336.8°Cat760mmHg
• Flash Point: 157.5°C
• Appearance: /
• Density: 1.271g/cm³
• Vapor Pressure: 4.29E-05mmHg at 25°C
• PKA: 4.20±0.10(Predicted)
• CAS DataBase Reference: 4-(mercaptomethyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(mercaptomethyl)benzoic acid(39088-65-8)
• EPA Substance Registry System: 4-(mercaptomethyl)benzoic acid(39088-65-8)

Safety Data

• Hazardous Substances Data: 39088-65-8(Hazardous Substances Data)

Usage

General Description

4-(mercaptomethyl)benzoic acid is a compound with the chemical formula C8H8O2S, possessing a molecular weight of 168.21 g/mol. It is classified as a benzoic acid derivative with a thiol group attached to the methyl group at the para position. This chemical is commonly used as a building block in the synthesis of pharmaceuticals, dyes, and agrochemicals. It has the potential to form complexes with various metals due to its thiol group, making it useful in various chemical and biological applications. Additionally, 4-(mercaptomethyl)benzoic acid can act as a weak acid, dissociating in aqueous solutions to release hydrogen ions.

InChI:InChI=1/C8H8O2S/c9-8(10)7-3-1-6(5-11)2-4-7/h1-4,11H,5H2,(H,9,10)/p-1

Upstream product

• 51776-12-6 4-(sulfanylmethyl)benzonitrile 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 1642-81-5 p-(chloromethyl)benzoic acid 
• 75472-97-8 4-(ethoxythiocarbonylthiomethyl)benzoic acid 
• 26496-94-6 Ethyl 4-(bromomethyl)benzoate 
• 263758-16-3 C₉H₁₀N₂O₂S*ClH 
• 1032290-97-3 4-tritylsulfanylmethyl-benzoic acid 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 99-94-5 p-Toluic acid 
• 383400-99-5 4-[(4-methoxy-phenyl)-diphenyl-methylsulfanylmethyl]-benzoic acid 

Downstream Products

• 142650-25-7 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoylthiomethyl)benzoic acid 
• 63684-45-7 C₁₆H₁₄O₄S₂ 
• 107167-64-6 C₄₂H₅₀O₄S₂ 
• 57624-33-6 ethyl 4-(mercaptomethyl)benzoate 
• 619-66-9 4-Carboxybenzaldehyde 
• 1057704-56-9 4-((4-chlorobenzylthio)methyl)benzoic acid 
• 1236136-49-4 4-(((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methylthio)methyl)benzoic acid 
• 132055-68-6 1,10,19,28-tetra<4-(acetylthiomethyl)benzoyl>-1,10,19,28-tetra-azacyclohexatriacontane 
• 132035-68-8 1,10,19,28-tetra<4-(mercaptomethyl)benzoyl>-1,10,19,28-tetra-azacyclohexatriacontane 
• 129018-27-5 4-(acetylthiomethyl)benzoyl chloride 
• 81509-60-6 2,5-bis-(p-bromomethylphenylmethylthiomethyl)thiophen 
• 81509-59-3 2,5-bis-(p-hydroxyphenylmethylthiomethyl)thiophen 
• 149280-80-8 4-{6-((E)-2-Methoxycarbonyl-vinyl)-5-[8-(4-methoxy-phenyl)-octyloxy]-pyridin-2-ylmethanesulfinylmethyl}-benzoic acid methyl ester 

Relevant articles and documents

Synthesis and structure-activity relationship of new cytotoxic agents targeting human glutathione-S-transferases

The 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexan-1-ol (NBDHEX, 1), a "suicide inhibitor" of the glutathione-S-transferase GSTP1-1, showed pro-apoptotic properties in tumor cells, but in vivo studies were limited by poor bioavailability and high af finity towards GSTM2-2, expressed in many noncancerous tissues. Here we describe the synthesis and biological characterization of new 1 analogs (2-40), in which the hydroxyhexyl portion at the C4-sulfur atom has been replaced with phenylcontaining moieties as well as substituted alkyl chains. Some of the new compounds displayed 10-100 times increased water-solubility (8, 11, 17, 26-28, 34, 35), and most of them showed higher GSTP1- 1 selectivity (2-20, 23-26, 31-33, 35) than 1. The presence of a phenyl ring with polar substituents is in general associated, with some exceptions (23, 24) to low cytotoxicity in osteosarcoma U-2OS cells. Differently, some alkyl derivatives possess cytotoxicity comparable (26, 34, 35) or higher (30, 32) than 1. Among the novel compounds, selected ones (26, 27, 34, and 35) deserve further investigation for their anticancer potential.

Exploring the differential recognition of DNA G-quadruplex targets by small molecules using dynamic combinatorial chemistry

Tuning affinities: Dynamic combinatorial chemistry has been employed to explore the effect of chemical modifications on the DNA G-quadruplex binding properties of anoxazole-based peptide macrocycle. Two dynamic libraries of molecules, containing cationic and carbohydrate motifs, respectively, were screened by using structurally diverse nucleic acid targets (see scheme; each colored shape represents a cation or carbohydrate). (Chemical Equation Presented).

Parallel synthesis of glycomimetic libraries: targeting a C-type lectin.

We have developed methods for the parallel synthesis of two libraries of non-carbohydrate-based analogues of mannose on a solid support. The natural product shikimic acid was used as a key building block. The ability of the compounds to block the binding of the C-type lectin MBP-A to a mannosylated surface was assessed in a high-throughput assay. Ten library members with inhibitory activities equivalent to that of alpha-methyl mannopyranoside were identified. [reaction: see text]