2153-11-9

Basic information

• Product Name: 2'-CHLORO-4-HYDROXYACETANILIDE
• Synonyms: 2'-CHLORO-4-HYDROXYACETANILIDE;2-CHLORO-N-(4-HYDROXYPHENYL)ACETAMIDE;AURORA KA-3271;2-chloro-N-(4-hydroxyphenyl)ethanamide
• CAS NO: 2153-11-9
• Molecular Formula: C₈H₈ClNO₂
• Molecular Weight: 185.61
• Mol File: 2153-11-9.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 419.4 °C at 760 mmHg
• Flash Point: 207.4 °C
• Appearance: /
• Density: 1.402 g/cm³
• Vapor Pressure: 1.26E-07mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: 2'-CHLORO-4-HYDROXYACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-CHLORO-4-HYDROXYACETANILIDE(2153-11-9)
• EPA Substance Registry System: 2'-CHLORO-4-HYDROXYACETANILIDE(2153-11-9)

Safety Data

• Hazardous Substances Data: 2153-11-9(Hazardous Substances Data)

Usage

Uses

4-(Chloroacetamido)phenol, is a building block used in the synthesis of various compounds such as synthesis of novel thiazolidinedione derivatives as irreversible allosteric IKK-β modulators

InChI:InChI=1/C8H8ClNO2/c9-5-8(12)10-6-1-3-7(11)4-2-6/h1-4,11H,5H2,(H,10,12)

Upstream product

• 123-30-8 4-amino-phenol 
• 541-88-8 Chloroacetic anhydride 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 87439-75-6 N-(4-Hydroxy-phenyl)-2-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetamide 
• 1214879-92-1 6-amino-7-cyano-N-(4-hydroxyphenyl)-2,3-dihydro-1H-pyrrolizine-5-carboxamide 
• 1412441-89-4 2-(2-(4-(dimethylamino)benzylidene)hydrazinyl)-N-(4-hydroxyphenyl)acetamide 
• 1412441-99-6 2-(3-(2,4-dichlorophenoxy)-2-(4-(dimethylamino)phenyl)-4-oxoazetidin-1-ylamino)-N-(4-hydroxyphenyl)acetamide 
• 1552323-04-2 N-(4-allyloxyphenyl)-2-(2,3-dihydroxypropylthio)acetamide 
• 1552323-03-1 methyl 3-(2-(4-allyloxyphenylamino)-2-oxoethylthio)propanoate 
• 1552322-93-6 N-(4-allyloxyphenyl)-2-(4-bromophenylthio)acetamide 
• 1552323-06-4 C₄₉H₅₆N₄O₈S₄ 
• 1552323-05-3 2-chloro-N-(4-(3-(2,3-dihydroxypropylthio)propoxy)phenyl)acetamide 
• 1552322-94-7 methyl 3-(3-(4-(2-chloroacetamido)phenoxy)propylthio)propanoate 
• 177206-64-3 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-N-(4-hydroxyphenyl)acetamide 
• 182502-68-7 SCP-1 

Relevant articles and documents

Design, synthesis and biological evaluation of novel thiazolidinedione derivatives as irreversible allosteric IKK-β modulators

The kinase known as IKK-β activates NF-κB signaling pathway leading to expression of several genes contributing to inflammation, immune response, and cell proliferation. Modulation of IKK-β kinase activity could be useful for treatment and management of such diseases. Starting from a discovered weakly active hit compound, twenty four thiazolidinedione-scaffold based chemical entities belonging to five series have been designed, synthesized and evaluated as potential IKK-β modulators. Among them, compounds 6q, 6r and 6u showed low micromolar IC50 values while compounds 6v, 6w, and 6x elicited submicromolar IC50 values equal to 0.4, 0.7 and 0.9 μM respectively. These submicromolar IC50 values are 243, 139 and 105 folds the value of the reported IC50 of the starting hit compound. Kinetic study of compounds 6v and 6w confirmed this class of modulators as irreversible inhibitors. LPS-treated RAW 264.7 macrophages proved the anti-inflammatory activity of compounds 6q and 6v. Assay of hERG inhibition demonstrated a safe profile of compound 6q suggesting it as a lead for further development of IKK-β modulators.

Antidiabetic compounds

Compounds for the treatment of hyperglycemia and/or diabetes are provided. The compounds, which inhibit the enzyme dipeptidyl peptidase (DPP-4), are based on the structure where X may be present or absent an may be OH, Ar is an aryl group; and n ranges from 0 to 5.

Thiazolidine-2,4-dione-based irreversible allosteric IKK-β kinase inhibitors: Optimization into in vivo active anti-inflammatory agents

Selective kinase inhibitors development is a cumbersome task because of ATP binding sites similarities across kinases. On contrast, irreversible allosteric covalent inhibition offers opportunity to develop novel selective kinase inhibitors. Previously, we

Substituted-3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and Stimulator for Interferon Genes (STING) modulators as cancer immunotherapeutics

Substituted-3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and related compounds, which are useful as inhibitors of ENPP1; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the ENPP1.