39086-61-8

Basic information

• Product Name: 2-chloro-N-ethylacetanilide
• Synonyms: 2-chloro-N-ethylacetanilide;Chloro-N-ethyl-N-phenylacetamide;2-chloro-N-ethyl-N-phenyl-ethanamide;Acetamide, 2-chloro-N-ethyl-N-phenyl-;Alpha-chloro-N-ethyl acetanilide
• CAS NO: 39086-61-8
• Molecular Formula: C₁₀H₁₂ClNO
• Molecular Weight: 197.66138
• EINECS: 254-283-2
• Mol File: 39086-61-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 35 °C
• Boiling Point: 280.1°Cat760mmHg
• Flash Point: 123.2°C
• Appearance: /
• Density: 1.169g/cm³
• Vapor Pressure: 0.00386mmHg at 25°C
• Refractive Index: 1.561
• PKA: 0.36±0.50(Predicted)
• CAS DataBase Reference: 2-chloro-N-ethylacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-N-ethylacetanilide(39086-61-8)
• EPA Substance Registry System: 2-chloro-N-ethylacetanilide(39086-61-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 39086-61-8(Hazardous Substances Data)

Usage

General Description

2-chloro-N-ethylacetanilide is a chemical compound that falls in the category of anilides, known for their primary usage in organic synthesis and production of dyes. The scientific formula for this compound is C10H12ClNO. It is characterized by the presence of a chlorine atom, which is indicative of its potential reactivity. Like all chemicals, it must be handled with care and proper safety measures should be adhered to avoid health hazards. Generally, it appears as a crystalline solid and it is commonly used in the creation of other complex compounds in pharmaceuticals and chemistry research.

InChI:InChI=1/C10H12ClNO/c1-2-12(10(13)8-11)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

Upstream product

• 103-69-5 N-ethyl-N-phenylamine 
• 79-04-9 chloroacetyl chloride 
• 79-11-8 chloroacetic acid 
• 4348-19-0 N-ethylaniline hydrochloride 

Downstream Products

• 108985-23-5 1-oxa-spiro[2.5]octane-2-carboxylic acid-(N-ethyl-anilide) 
• 100609-03-8 α,β-epoxy-isovaleric acid-(N-ethyl-anilide) 
• 46892-89-1 N-ethyl-2-morpholin-4-yl-N-phenyl-acetamide 
• 107348-02-7 Diethyl-dithiocarbamic acid (ethyl-phenyl-carbamoyl)-methyl ester 
• 99275-60-2 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-N-ethyl-N-phenyl-acetamide 
• 120508-35-2 2-Chloro-N-ethyl-N-phenyl-thioacetamide 
• 66325-67-5 diethyl (2-(ethyl(phenyl)amino)-2-oxoethyl)phosphonate 
• 529-65-7 N-ethylacetanilide 
• 103-69-5 N-ethyl-N-phenylamine 
• 1243284-06-1 2-[(2R,6R,11R)-8-hydroxy-6,11-dimethyl-1,4,5,6-tetrahydro-2,6-methano-3-benzazocin-3(2H)-yl]-N-ethyl-N-phenylacetamide 
• 226952-92-7 6-chloro-N-ethyl-8,9-dihydro-9-methyl-8-oxo-2-phenyl-N-phenyl-7H-purin-7-acetamide 
• 99275-66-8 4-Hydroxy-1-oxo-1,2-dihydro-isoquinoline-3-carboxylic acid ethyl-phenyl-amide 
• 103148-97-6 N-Ethyl-2-(triphenylphosphoranyliden)acetanilid 
• 103149-04-8 N-Ethyl-2,3-butadienanilid 

Relevant articles and documents

Palladium-catalyzed olefination of aryl/alkyl halides with trimethylsilyldiazomethane via carbene migratory insertion

The direct olefination of aryl/alkyl halides with trimethylsilyldiazomethane (TMSD) as a C1- or C2-unit was achieved successfully via a metal carbene migratory insertion process, which offered a new access to afford (E)-vinyl silanes and (E)-silyl-substituted α,β-unsaturated amides in good yields and high chemoselectivity.

Anti-proliferative activity, molecular modeling studies and interaction with calf thymus DNA of novel ciprofloxacin analogues

Abstract: In our pursuit to expand new potential anticancer leads, a series of eighteen novel 1-cyclopropyl-6-fluoro-4-oxo-7-(4-substituted piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid analogues have been synthesized, characterized and evaluated anti-proliferative activity against five human cancer cell lines such as A549 (lung cancer), Mia Paca (pancreatic cancer), HeLa (cervical cancer), MDA MB-231 (breast cancer), MCF-7 (breast cancer) and normal embryonic kidney?cell line (HEK) were carried out using MTT assay. Few of the synthesized analogues exhibited potent anticancer activity against the cancer cell lines at a lower concentration. The synthesized compounds showed the less toxic effect on normal human embryonic kidney?cell line (HEK) compared with doxorubicin. Noticeably, compound 3o exhibited potent activity against all five cancer cell lines compared with ciprofloxacin. Further study exposed that compound 3o could competently intercalate into calf thymus DNA to form 3o-DNA complex which might block DNA replication to apply anti-proliferative activity. Docking simulation studies supported by molecular interactions with DNA type II topoisomerase. These derivates can become lead structures for the development of potential anticancer drugs. Graphical Abstract: Eighteen CP analogues were synthesized and evaluated for anti-proliferative activity. The interactions with DNA topoisomerase II were supported by molecular docking studies. 3o showed promising anticancer activity than CP against MCF7 cell line and interaction with calf thymus DNA was studied by fluorescence spectroscopy.[Figure not available: see fulltext.].

Electrochemical reduction of 2-chloro-N-phenylacetamides at carbon and silver cathodes in dimethylformamide

Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the direct electrochemical reduction of 2-chloro-N-methyl-N-phenylacetamide (1a), 2-chloro-N-ethyl-N-phenylacetamide (1b), and 2-chloro-N-phenylacetamide (1c) at carbon and silver cathodes, as well as the catalytic reduction of these compounds by electrogenerated nickel(I) salen, in dimethylformamide (DMF) containing 0.050 M tetramethylammonium tetrafluoroborate (TMABF4). Cyclic voltammograms for reduction of 1a and 1b show a single irreversible cathodic peak for cleavage of the carbon-chlorine bond, but two irreversible cathodic peaks are observed in cyclic voltammograms for reduction of 1c. Controlled-potential reduction of 1a and 1b gives mixtures of dechlorinated amide and N-alkyl-N-phenylaniline, whereas bulk electrolyses of 1c afford N-phenylacetamide in almost quantitative yield. In addition, bulk electrolyses of 1a and 1b result in the formation of very small amounts of dimeric species that arise from coupling of the radical intermediate formed by one-electron cleavage of the carbon-chlorine bond. On the basis of the coulometric n values and product distributions, together with computations based on density functional theory, we propose mechanistic pictures for the reduction of 1a and 1b that involve radical intermediates, whereas reduction of 1c involves carbanion intermediates.