21262-52-2

Basic information

• Product Name: 2'-CHLOROPROPIONANILIDE
• Synonyms: 2'-CHLOROPROPIONANILIDE;N-Phenyl-2-chloro-2-methylacetamide;N-Phenyl-2-chloropropionamide;2-chloro-N-phenylpropanamide(SALTDATA: FREE);NSC99819;T0517-5848
• CAS NO: 21262-52-2
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.6348
• Mol File: 21262-52-2.mol

Chemical Properties

• Boiling Point: 340.232 °C at 760 mmHg
• Flash Point: 159.567 °C
• Appearance: /
• Density: 1.218 g/cm³
• Vapor Pressure: 8.72E-05mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 2'-CHLOROPROPIONANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-CHLOROPROPIONANILIDE(21262-52-2)
• EPA Substance Registry System: 2'-CHLOROPROPIONANILIDE(21262-52-2)

Safety Data

• Hazardous Substances Data: 21262-52-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2'-Chloropropionanilide is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs and medications.
Used in Agrochemical Industry:
2'-Chloropropionanilide is used as an active ingredient in the production of insecticides and miticides. Its insecticidal and acaricidal properties make it an effective solution for controlling pests in agricultural settings.
Used in Fine Chemicals and Dyes Industry:
2'-Chloropropionanilide is used as a precursor for the synthesis of various fine chemicals and dyes. Its versatility in chemical reactions allows it to be a valuable component in the creation of a wide range of products.
Safety Precautions:
It is important to handle 2'-Chloropropionanilide with care, as it is considered harmful if swallowed, inhaled, or if it comes into contact with skin. Proper safety measures should be taken to minimize exposure and ensure the safe use of this chemical compound.

InChI:InChI=1/C9H10ClNO/c1-7(10)9(12)11-8-5-3-2-4-6-8/h2-7H,1H3,(H,11,12)

Upstream product

• 7623-09-8 2-chloropropionyl chloride 
• 62-53-3 aniline 
• 103-84-4 Acetanilid 
• 10026-13-8 phosphorus pentachloride 
• 106942-22-7 lactanilide 
• 71-43-2 benzene 
• 67097-66-9 N-chloro-propionanilide 
• 598-78-7 (R,S)-2-chloropropionic acid 
• 42308-20-3 2-bromopropionanilide 
• 19103-79-8 2-chloro-propionyl isothiocyanate 

Downstream Products

• 21262-08-8 N-(4-bromophenyl)-2-chloropropanamide 
• 81931-33-1 N-phenyl-2-pyrrolidinyl-propionamide 
• 131859-61-5 2-(6-Methoxy-2,2-dimethyl-4-oxo-chroman-7-yloxy)-N-phenyl-propionamide 
• 131859-59-1 2-(2,2-Dimethyl-4-oxo-chroman-7-yloxy)-N-phenyl-propionamide 
• 125506-46-9 diethyl (1-oxo-1-(phenyl-amino)propan-2-yl)phosphonate 
• 596808-18-3 2-(2-chloropyridin-3-yloxy)-N-phenylpropionamide 
• 102879-24-3 2-methyl-N-phenylaziridine 
• 16955-09-2 2-anilino-1-propanol 
• 622-80-0 N-propylaniline 
• 768-52-5 N-Isopropylaniline 
• 6288-14-8 2-(acetyloxy)-N-phenylpropanamide 
• 1570275-40-9 2-methyl-N,4,4-triphenylbutanamide 
• 1048970-82-6 N-phenyl-2-[(2-hydroxyethyl)thio]propanamide 
• 104657-00-3 1-[4-N-(α-chloro-α-methylacetyl)aminophenyl]-2-chloropropanone 

Relevant articles and documents

Optimization of bifunctional piperidinamide derivatives as σ1R Antagonists/MOR agonists for treating neuropathic pain

Here, we describe the optimization, synthesis, and associated pharmacological analgesic activities of a new series of bifunctional piperidinamide derivatives as sigma-1 receptor (σ1R) antagonists and mu opioid receptor (MOR) agonists. The new compounds were evaluated in vitro in σ1R and MOR binding assays. The most promising compound 114 (also called HKC-126), showed superior affinities for σ1R and MOR and good selectivity to additional receptors related to pain. Compound 114 showed powerful dose-dependent analgesic effects in the acetic acid writhing test, formalin test, hot plate test, and chronic constriction injury (CCI) neuropathic pain model. In contrast to an equianalgesic dose of fentanyl, compound 114 produced fewer opioid-like side effects, such as reward liability, respiratory depression, physical dependence, and sedation. Lastly, the pharmacokinetic properties of this drug were also acceptable, and these results suggest that compound 114, as a mixed σ1R/MOR ligand, has potential for treating neuropathic pain.

Regioselective Thermal [3+2]-Dipolar Cycloadditions of α-Diazoacetates with α-Sulfenyl/Sulfinyl/Sulfonyl-β-Chloroacrylamide Derivatives to Form Densely Functionalised Pyrazoles

Highly regioselective synthetic methodology leading to densely functionalised C(3), C(4) and C(5) substituted pyrazoles 10a–q, 14a-i and 16a–g via thermal [3+2]-dipolar cycloaddition, of α-diazoacetates and α-thio-β-chloroacrylamides, at the sulfide, sulfoxide and sulfone levels of oxidation, is described. This method allows access to C(4)-sulfenyl or sulfonyl pyrazoles, through migration of the sulfur substituent at the sulfide and sulfone oxidation levels, while elimination of the sulfinyl group leading to 3,5-disubstituted pyrazoles, is observed. While the sulfide migration is readily rationalised, the carbon to carbon 1,2-sulfonyl migration is unprecedented and mechanistically intriguing. The synthetically versatile generation of densely functionalised pyrazoles containing substituents amenable to further modification offers advantages over alternative synthetic routes. Isolation of the N-alkylated pyrazoles 11a and 12a as by-products from the cycloaddition through further reaction of the pyrazoles 10 with excess α-diazoacetate, proved useful in rationalising the tautomeric behaviour evident in the NMR spectra of the pyrazoles, with the position of tautomeric equilibrium influenced by solvent and substituents.

Inhibitory Effects of New Mercapto Xanthine Derivatives in Human mcf7 and k562 Cancer Cell Lines

A series of new 2-methyl-2-[(1,3-Diethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)thio]-N- substituted arylacetamides were synthesized. The antitumor activity of these purine based compounds were evaluated on breast cancer (MCF7) and leukemic cancer (K562) cell lines via cell viability assay utilizing the tetrazolium dye 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). These results were substantiated using computer docking experiments (LigandFit docking engine and PMF scoring function) which predict that the antitumor activity of these new compounds may be attributable to their abilities to effectively bind and block oncogenic tyrosine kinases, particularly bcr/abl.

Dichloromethane as a chlorination reagent for α-bromocarbonyl compounds in the presence of a copper catalyst

We found that dichloromethane is a powerful chlorinating reagent for the congested 3° and 2° Csp3Br bond of α-bromocarbonyl amides, esters, and ketones. In the presence of an appropriate copper complex as a catalyst, the desired chlorination occurred within an hour. Control experiments revealed that in situ-generated CuCl2 is a key chlorinating agent that reacts with the 3° or 2° alkyl radicals generated by the reaction between an α-bromocarbonyl compound and a Cu(I) salt.

Acetobenzylamide piperazine derivative and application thereof as cranial nerve protective agent

The invention discloses an acetobenzylamide piperazine derivative and an application thereof as a cranial nerve protective agent. Pharmacological experiments verify that the compound disclosed by the invention shows an obvious effect against glutamic acid-induced neuron exitotoxicity in vitro and obvious anti-anoxia activity in a mouse, and a herg test further shows that the compound disclosed by the invention does not have the risk of cardiotoxicity. Therefore, the compound disclosed by the invention has the advantages of being high in activity, less in side effect and good in druggability. The compound and a medicinal preparation thereof have a good curative effect for treating cranial nerve injury diseases, for example, stroke and related diseases and do not have the risk of cardiotoxicity. The acetobenzylamide piperazine derivative is a free alkali or salt of a compound with a chemical structural formula shown in the description.

Friedel-crafts alkylation of N-(2-chloropropionyl)aniline and the generation mechanism of byproducts

The cyclization of N-(2-chloropropionyl)aniline to 3-methylindolin-2-one through Friedel-Crafts alkylation was studied. It was found that N-phenylacrylamide (12.6%) and 3,4-dihydro-2(1H)-quinolinone (1.5%) as main byproducts were obtained. On the basis of the mechanism of Friedel-Crafts alkylation, the generation mechanisms of these two compounds were proposed.

GPR17-MODULATING COMPOUNDS, DIAGNOSTIC AND THERAPEUTIC USES THEREOF

Disclosed are compounds able to modulate the activity of the GPR17 receptor in a highly specific way, which are useful in the treatment and diagnosis of diseases or dysfunctions involving the activation of said receptor. In particular, the compounds according to the invention can be used for neuroprotective and/or reparatory purposes, in cerebral, cardiac and renal ischaemia, in cerebral trauma, in chronic neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), and in demyelinating diseases such as multiple sclerosis.

Visible light photoredox-catalysed intermolecular radical addition of α-halo amides to olefins

We present α-chloro amides as a new class of α-acetyl radical precursors, which undergo a tin-free, photoredox-catalysed intermolecular α-alkylation with various olefins exclusively in an anti-Markovnikov fashion. The reaction represents a reductive atom

In silico and experimental identification of non ulcerogenic antiinflammatory agents: 3-Thio substituted-4,5-diaryl-4H-1,2,4-triazoles

A new series of 4,5 diaryl-1,2,4-triazole-3-thione substituted carboxamides have been designed, synthesized and tested for their analgesic and antiinflammatory potential. All the tested compounds exhibit antiinflammatory activity comparable to that of standard drugs rofecoxib and diclofenac. Some compounds demonstrate significant analgesic activity in contrast to reference drugs. Compound 9c has emerged as a highly potent lead compound. Ulcerogenic studies of synthesized compounds and rofecoxib show nil or negligible ulcerogenic effect compared to diclofenac. In silico analysis (docking studies) of the most active compound 9c has revealed hypothetical binding mode of the target compound to the cyclooxygenase isoenzyme (COX-2). Docking study has anticipated stereoselective binding mode for the most active compound 9c.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATION

The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of inflammation may he formulated for oral buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of Type II diabetes, Type I diabetes, insulin resistance, cardiovascular disease, arrhythmia, atherosclerosis, coronary artery disease, hypertriglyceridemia, dyslipidemia, retinopathy, nephropathy, neuropathy, macular adema, arthritis, osteoarthritis, rheumatoid arthritis, inflammatory bowel syndrome, neudegeneration, Alzheimer's disease, Huntington's disease. Ulcerative colitis, Crohn's disease. Multiple Sclerosis, muscular dystropthy, metabolic syndrome, fatty liver, bone diseases, inflammatory diseases.