5740-34-1

Basic information

• Product Name: α-Mercaptobenzeneacrylic acid
• Synonyms: 2-Mercapto-3-phenylacrylic acid;2-Mercapto-3-phenylpropenoic acid;RMI-71653;α-Mercaptobenzeneacrylic acid;α-Mercapto-β-phenylacrylic acid
• CAS NO: 5740-34-1
• Molecular Formula: C₉H₈O₂S
• Molecular Weight: 180.2236
• Mol File: 5740-34-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 126-127 °C
• Boiling Point: 337.3°Cat760mmHg
• Flash Point: 157.8°C
• Appearance: /
• Density: 1.297g/cm³
• Vapor Pressure: 5.76E-11mmHg at 25°C
• Refractive Index: 1.622
• PKA: 3.01±0.10(Predicted)
• CAS DataBase Reference: α-Mercaptobenzeneacrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: α-Mercaptobenzeneacrylic acid(5740-34-1)
• EPA Substance Registry System: α-Mercaptobenzeneacrylic acid(5740-34-1)

Safety Data

• Hazardous Substances Data: 5740-34-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 29, p. 427, 1951 DOI: 10.1139/v51-051

InChI:InChI=1/C20H18N2O3/c1-12(23)13-8-9-19-18(11-13)16-6-3-7-17(16)20(21-19)14-4-2-5-15(10-14)22(24)25/h2-6,8-11,16-17,20-21H,7H2,1H3

Upstream product

• 5178-04-1 3-methyl-5-benzylidenerhodanine 
• 79788-56-0 5-(Methylamino-phenyl-methyl)-3-phenyl-2-thioxo-thiazolidin-4-one 
• 3806-42-6 5-benzylidene-2-thioxothiazolidin-4-one 
• 100727-15-9 3-Allyl-5-benzyliden-2-thioxothiazolidin-4-on 
• 100-52-7 benzaldehyde 
• 622-29-7 N-Benzylidenemethylamine 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 3806-42-6 (Z)-5-benzylidene-2-thioxothiazolidin-4-one 
• 1151944-57-8 (Z)-2-(5-benzylidene-4-oxo-2-thioxothiazolidin-3-yl)acetic acid 

Downstream Products

• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 99033-95-1 2-hydroxyimino-3-phenylpropanoic acid 
• 72772-24-8 S(+)-2-mercapto-3-phenylpropionic acid 
• 93655-62-0 α,α'-disulfanediyl-di-cinnamic acid 
• 42056-21-3 5-benzylidene-3-(4-chloro-phenyl)-2-phenyl-thiazolidin-4-one 
• 42056-22-4 5-benzylidene-3-(4-bromo-phenyl)-2-phenyl-thiazolidin-4-one 
• 104484-26-6 3-benzylidene-6-ethoxycarbonyl-1,4-oxathiin-2(3H)-one 
• 104484-36-8 (E)-2-(1-Ethoxycarbonyl-2-oxo-2-phenyl-ethylsulfanyl)-3-phenyl-acrylic acid 
• 104484-08-4 α-acetylthio-β-phenylacrylic acid 
• 104484-30-2 (Z)-2-(2-Oxo-propylsulfanyl)-3-phenyl-acrylic acid 
• 79878-53-8 5-benzylidene-2-ethoxycarbonylmethyl-2-thiazolin-4-one 
• 104484-29-9 α-(2-oxo-2-phenylethylthio)-β-phenylacrylic acid 
• 79421-53-7 2-Cyanomethyl-5-benzylidene-2-thiazolin-4-one 
• 104484-33-5 α-(1-ethoxycarbonyl-2-oxopropylthio)-β-phenylacrylic acid 

Relevant articles and documents

Structure activity relationship studies on rhodanines and derived enethiol inhibitors of metallo-β-lactamases

Metallo-β-lactamases (MBLs) enable bacterial resistance to almost all classes of β-lactam antibiotics. We report studies on enethiol containing MBL inhibitors, which were prepared by rhodanine hydrolysis. The enethiols inhibit MBLs from different subclasses. Crystallographic analyses reveal that the enethiol sulphur displaces the di-Zn(II) ion bridging ‘hydrolytic’ water. In some, but not all, cases biophysical analyses provide evidence that rhodanine/enethiol inhibition involves formation of a ternary MBL enethiol rhodanine complex. The results demonstrate how low molecular weight active site Zn(II) chelating compounds can inhibit a range of clinically relevant MBLs and provide additional evidence for the potential of rhodanines to be hydrolysed to potent inhibitors of MBL protein fold and, maybe, other metallo-enzymes, perhaps contributing to the complex biological effects of rhodanines. The results imply that any medicinal chemistry studies employing rhodanines (and related scaffolds) as inhibitors should as a matter of course include testing of their hydrolysis products.

Synthesis and antimicrobial activities of gold(I) sulfanylcarboxylates

Reaction of NaAuCl4H2O and thiodiglycol (1:3 molar ratio) with 3-(aryl)-2-sulfanylpropenoic acids, H2xspa0[x:p03-phenyl- , f03-(2-furyl)-, t03-(2-thienyl)-, o-py03-(2-pyridyl)-, Clp03-(2-chlorophenyl)- , -o-mp03- (2-methox

New structural features in triphenylphosphinesilver(I) sulfanylcarboxylates

We investigated the reactions of 1.5 : 1 : 1 mole ratio mixtures of triphenylphosphine, silver nitrate and 3-(aryl)-2-sulfanylpropenoic acids H 2xspa in chloroform/water, where in the acid nomenclature, spa = 2-sulfanylpropenoato and x = p, Clp