3460-04-6

Basic information

• Product Name: 3-CHLORO-N-PHENYLPROPANAMIDE
• Synonyms: 3-CHLOROPROPIONANILIDE;3-CHLORO-N-PHENYLPROPANAMIDE;3-CHLORO-N-PHENYL-PROPIONAMIDE;3-Chloro-N-phenylpropionamide 3-Chloropropionanilide;Propanamide, 3-chloro-N-phenyl-
• CAS NO: 3460-04-6
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• Mol File: 3460-04-6.mol
• Article Data: 38

Chemical Properties

• Melting Point: 119.5-120.5 °C
• Boiling Point: 360.2 °C at 760 mmHg
• Flash Point: 171.7 °C
• Appearance: /
• Density: 1.22 g/cm³
• Vapor Pressure: 2.25E-05mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 14.20±0.70(Predicted)
• CAS DataBase Reference: 3-CHLORO-N-PHENYLPROPANAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-N-PHENYLPROPANAMIDE(3460-04-6)
• EPA Substance Registry System: 3-CHLORO-N-PHENYLPROPANAMIDE(3460-04-6)

Safety Data

• Hazardous Substances Data: 3460-04-6(Hazardous Substances Data)

Usage

General Description

3-Chloro-N-phenylpropanamide is a chemical compound with the formula C9H10ClNO. It is a white to off-white crystalline solid with a molecular weight of 185.63 g/mol. 3-CHLORO-N-PHENYLPROPANAMIDE is commonly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It has a wide range of applications in the pharmaceutical and chemical industries, including as an intermediate in the production of drugs and as a reagent in organic synthesis. 3-Chloro-N-phenylpropanamide is also known to have some biological activity and may have potential therapeutic uses, although further research is needed to fully understand its medicinal properties.

InChI:InChI=1/C9H10ClNO/c10-7-6-9(12)11-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)

Upstream product

• 802294-64-0 propionic acid 
• 62-53-3 aniline 
• 19565-19-6 3-chloropropionylisothiocyanate 
• 625-36-5 2-chloropropionyl chloride 

Downstream Products

• 6833-29-0 N-phenyl pentanethioamide 
• 895250-80-3 C₁₂H₁₃N₃O 
• 1125436-62-5 C₁₁H₁₂N₄O 
• 4497-03-4 3-(morpholin-4-yl)-N-phenylpropanamide 
• 54197-66-9 3,4-dihydro-6-hydroxy-2(1H)-quinolinone 

Relevant articles and documents

Synthesis, in silico Study and Antileishmanial Evaluation of New Selenides Derived from 7-Chloro-quinoline and N-Phenylacetamides

This study describes a virtual screening performed for two series of selenides (28 compounds), derived from N-phenylacetamides chlorides and 7-chloro-quinoline, to determine their potential for leishmanicidal activity against Leishmania amazonensis and Leishmania donovani. Seven compounds were predicted as potential leishmanicides; therefore, they were synthesized from elemental selenium, as a precursor for the production of NaHSe, and subsequent reactions with 4,7-dichloro-quinoline and N-phenylacetamides chlorides were performed. The compounds were characterized by infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), and sent for in vitro cytotoxicity tests against L. amazonensis and were found to be active and selective, and two compounds presented half-maximal inhibitory concentrations (IC50) of 5.67 and 10.81 μg mL-1. They also presented good interaction energies in the docking study, suggesting that may exert their effects by inhibiting the N-myristoyltransferase and O-acetylserine sulfhydrylase enzymes in parasites.

Synthesis and Exploration of Abscisic Acid Receptor Agonists Against Dought Stress by Adding Constraint to a Tetrahydroquinoline-Based Lead Structure

New oxotetrahydroquinolinyl- and oxindolinyl sulfonamides interacting with RCAR/(PYR/PYL) receptor proteins were identified as lead structures against drought stress in crops starting from protein docking studies of a sulfonamide lead structure, followed by in-depth SAR studies. Optimized five to six step synthetic approaches via substituted amino oxo-tetrahydro-quinolines and amino oxo-indolines as essential intermediates gave access to the envisaged oxo-tetrahydroquinolinyl and oxindolinyl sulfonamides. Whilst oxo-tetrahydroquinolinyl sulfonamides with additional carbon substituents or spiro-cycloalkyl groups exhibited only low to moderate target affinities, the corresponding spiro-oxindolinyl and oxo-tetrahydroquinolinyl sulfonamides carrying optimized N-substituents revealed strong interactions with RCAR/(PYR/PYL) receptor proteins in Arabidopsis thaliana. Remarkably, the in vitro activity observed for these new compounds was on the same level as observed for the naturally occurring plant hormone in line with strong efficacy against drought stress in-vivo (canola and wheat as broad-acre crops).

Demonstration of in Vitro Resurrection of Aged Acetylcholinesterase after Exposure to Organophosphorus Chemical Nerve Agents

After the inhibition of acetylcholinesterase (AChE) by organophosphorus (OP) nerve agents, a dealkylation reaction of the phosphylated serine, referred to as aging, can occur. When aged, known reactivators of OP-inhibited AChE are no longer effective. Realkylation of aged AChE may provide a route to reversing aging. We designed and synthesized a library of quinone methide precursors (QMPs) as proposed realkylators of aged AChE. Our lead compound (C8) from an in vitro screen successfully resurrected 32.7 and 20.4% of the activity of methylphosphonate-aged and isopropyl phosphate-aged electric-eel AChE, respectively, after 4 days. C8 displays properties of both resurrection (recovery from the aged to the native state) and reactivation (recovery from the inhibited to the native state). Resurrection of methylphosphonate-aged AChE by C8 was significantly pH-dependent, recovering 21% of activity at 4 mM and pH 9 after only 1 day. C8 is also effective against isopropyl phosphate-aged human AChE.