18330-64-8

Basic information

• Product Name: 4-amino-3-thiocyanatobenzoic acid
• Synonyms: 4-amino-3-thiocyanatobenzoic acid
• CAS NO: 18330-64-8
• Molecular Formula: C₈H₆N₂O₂S
• Molecular Weight: 194
• Mol File: 18330-64-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 397.6°C at 760 mmHg
• Flash Point: 194.3°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 4.91E-07mmHg at 25°C
• Refractive Index: 1.692
• CAS DataBase Reference: 4-amino-3-thiocyanatobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-3-thiocyanatobenzoic acid(18330-64-8)
• EPA Substance Registry System: 4-amino-3-thiocyanatobenzoic acid(18330-64-8)

Safety Data

• Hazardous Substances Data: 18330-64-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6N2O2S/c9-4-13-7-3-5(8(11)12)1-2-6(7)10/h1-3H,10H2,(H,11,12)

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 150-13-0 4-amino-benzoic acid 
• 333-20-0 potassium thioacyanate 
• 540-72-7 sodium thiocyanide 

Downstream Products

• 14543-45-4 4-amino-3-mercaptobenzoic acid 
• 1370024-75-1 2-(2-chlorophenyl)-3-(4-methylphenyl)-2,3-dihydroimidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 1370409-59-8 2-(2-chlorophenyl)-3-(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 1370025-25-4 2-(2-chlorophenyl)-3-[4-(methylsulfanyl) phenyl]-2,3-dihydroimidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 1370024-54-6 2-(4-methoxyphenyl)-3-(4-methylphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 1280582-32-2 2,3-bis(4-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 1370409-52-1 2-(4-methoxyphenyl)-3-[4-(methylsulfanyl) phenyl]imidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 1370024-36-4 2-(2,4-dichlorophenyl)-3-(4-methylphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 1370409-53-2 2-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)imidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 1370023-99-6 2-(2,4-dichlorophenyl)-3-[4-(methylsulfanyl)phenyl]imidazo[2,1-b][1,3]benzothiazole-7-carboxylic acid 
• 93-85-6 2-aminobenzothiazole-6-carboxylic acid 
• 6285-57-0 2-amino-6-nitrobenzothiazole 
• 1370409-55-4 2-(4-methoxyphenyl)-3-[4-(methylsulfanyl)phenyl]-7-nitroimidazo[2,1b][1,3] benzothiazole 
• 1370409-54-3 2-(2,4-dichlorophenyl)-3-(4-methylphenyl)-7-nitroimidazo[2,1-b][1,3]benzothiazole 

Relevant articles and documents

Synthesis and preliminary in-vitro cytotoxic activity of novel substituted diaryl-imidazo [2, 1, b]-benzothiazole derivatives

A novel series of substituted diaryl imidazo[2, 1-b]benzothiazole derivatives (8a-y) were synthesized by condensation reaction between 2-amino benzothiazole derivatives (3a-g) and substituted a-bromo-1, 2-(substituted) diaryl-1-ethanones (7a-i). The structures of the synthesized compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopical data. The compounds (8a-y) were evaluated for their in-vitro cytotoxic activity on murine (B16F10) and human (MCF-7) cancer cells by using MTT assay. From the in vitro studies compounds 8p, 8u and 8y were found most effective with an IC50 range of 0.56-27.50 μM in MCF-7 and 2.57-36.54 μM in B16F10 cells.

Dibenzothiazoles as novel amyloid-imaging agents

Novel dibenzothiazole derivatives were synthesized and evaluated as amyloid-imaging agents. In vitro quantitative binding studies using AD brain tissue homogenates showed that the dibenzothiazole derivatives displayed high binding affinities with Ki values in the nanomolar range (6.8-36 nM). These derivatives are relatively lipophilic with partition coefficients (logP oct) in the range of 1.25-3.05. Preliminary structure-activity relationship studies indicated dibenzothiazole derivatives bearing electron-donating groups exhibited higher binding affinities than those bearing electron-withdrawing groups. A lead compound was selected for its high binding affinity and radiolabeled with [125I] through direct radioiodination using sodium [125I] iodide in the presence of Chloramine T. The radioligand (4-[2,6′]dibenzothiazolyl-2′-yl-2-[125I]-phenylamine) displayed moderate lipophilicity (logP oct, 2.70), very good brain uptake (3.71 ± 0.63% ID/g at 2 min after iv injection in mice), and rapid washout from normal brains (0.78% and 0.43% ID/g at 30 and 60 min, respectively). These studies indicated that lipophilic dibenzothiazole derivatives represent a promising pharmacophore for the development of novel amyloid-imaging agents for potential application in Alzheimer's disease and related neurodegenerative disorders.

An improved preparation of 4-amino-3-mercaptobenzoic acid

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