34006-49-0

Usage

Uses

Used in Pharmaceutical Industry:
2-chloro-4-nitroacetophenone is used as a synthetic intermediate for the preparation of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 2-chloro-4-nitroacetophenone serves as a valuable compound for understanding the reactivity and properties of substituted acetophenones. It can be used to study the effects of different substituents on the chemical behavior of acetophenone derivatives.
Used in the Synthesis of Cytotoxic Compounds:
2-chloro-4-nitroacetophenone is used as a reagent in the preparation of tetrahydropyrrolo[3,2-c]azepin-4-ones, which are known for their cytotoxic properties. These compounds have potential applications in the development of anticancer drugs, making 2-chloro-4-nitroacetophenone an important compound in the fight against cancer.

InChI:InChI=1/C8H6ClNO3/c9-5-8(11)6-1-3-7(4-2-6)10(12)13/h1-4H,5H2

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 122-04-3 4-nitro-benzoyl chloride 
• 100-19-6 (4-nitrophenyl)ethanone 
• 100-13-0 4-nitrostyrene 
• 73805-24-0 α-chloro-p-nitrostyrene oxide 
• 4203-31-0 2-diazo-1-(4-nitrophenyl)ethanone 
• 99-81-0 4-Nitrophenacyl bromide 
• 54075-25-1 4-nitro-α-(trichloromethyl)benzyl alcohol 
• 67-56-1 methanol 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 6531-13-1 1-[4-nitrophenyl]-1-ethanol 
• 110944-98-4 2-iodo-1-(4-nitrophenyl)ethanone 

Downstream Products

• 65921-30-4 2-(4-nitrophenyl)-2-oxoethyl acetate 
• 21427-72-5 7-chloro-2-(4-nitro-phenyl)-3H-pyrido[2,3-b][1,4]thiazine 
• 119730-17-5 6-methyl-2-((2-(4-nitrophenyl)-2-oxoethyl)thio)pyrimidin-4(3H)-one 
• 102183-91-5 4-(4-nitrophenyl)-N-phenyl-1,3-thiazol-2-amine 
• 102183-93-7 2-imino-4-(4-nitrophenyl)-3-phenyl-2,3-dihydrothiazole 
• 2104-09-8 4-(4-nitro-phenyl)-thiazol-2-ylamine 
• 1253787-98-2 2-morpholino-2-(cyclohexen-1-yl)-4'-nitroacetophenone 
• 1434751-60-6 2-benzoyl-4-(4-nitrophenyl)-1-phenylbut-2-ene-1,4-dione 
• 1444827-58-0 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 119730-71-1 3-(4-nitrophenyl)-7-methyl-5H-thiazolo<3,2-a>pyrimidin-5-one 
• 119730-75-5 3-(4-nitrophenyl)-5H-thiazolo<3,2-a>pyrimidin-5-one 
• 119730-63-1 2-(4-nitrobenzoylmethylene)-2,3-dihydropyrimidin-4(1H)-one 
• 6388-74-5 (S)-2-(4-nitrophenyl)oxirane 
• 131213-57-5 2'-imino-4-(4-nitro-phenyl)-[2,3']bithiazolyl-4'-one 

Relevant academic research and scientific papers

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.

Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source

An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.

Cascade Trisulfur Radical Anion (S3?-) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles

Trisulfur radical anion (S3?-) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3?- is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C-S and N-S bonds via S3?- addition and electron detosylation under mild conditions.

Facile and efficient preparation of α-halomethyl ketones from α-diazo ketones catalyzed by iron(III) halides and silica gel

An efficient and mild method for the synthesis of α-halomethyl ketones from α-diazo ketones was developed using ferric chloride or bromide as the halogen source and silica gel as the hydrogen source, with good to excellent yields.

Systematic Synthesis of Diphenyl-Substituted Carotenoids as Molecular Wires

A general method for the construction of diphenyl-substituted carotenoids has been developed through the stereoselective synthesis of dienyl sulfones with a phenyl substituent. Systematic synthetic pathways to the dienyl sulfones were delineated starting from readily available acetophenones with para-substituent X of various electronic natures, which provided the carotenoids with diverse physicochemical characteristics. The sulfone olefination method together with the Ramberg–B?cklund reaction produced a 9,9′-cis-10,10′-diphenylcarotene and all-trans-9,9′-diphenylcarotenes. Conductance measurements of the all-trans carotenoids by the scanning tunnelling microscopy break-junction method revealed a positional effect of the phenyl groups as well as a polar effect of the phenyl substituent X according to the electronic nature.

Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane

A configurationally simple and robust semibatch apparatus for the in situ on-demand generation of anhydrous solutions of diazomethane (CH2N2) avoiding distillation methods is presented. Diazomethane is produced by base-mediated decomposition of commercially available Diazald within a semipermeable Teflon AF-2400 tubing and subsequently selectively separated from the tubing into a solvent- and substrate-filled flask (tube-in-flask reactor). Reactions with CH2N2 can therefore be performed directly in the flask without dangerous and labor-intensive purification operations or exposure of the operator to CH2N2. The reactor has been employed for the methylation of carboxylic acids, the synthesis of α-chloro ketones and pyrazoles, and palladium-catalyzed cyclopropanation reactions on laboratory scale. The implementation of in-line FTIR technology allowed monitoring of the CH2N2 generation and its consumption. In addition, larger scales (1.8 g diazomethane per hour) could be obtained via parallelization (numbering up) by simply wrapping several membrane tubings into the flask.

High-yielding aqueous synthesis of chloroacetophenones and aroyl chlorohydrins

The use of large amounts of volatile organic solvents in industrial chemical processes contributes to widespread environmental pollution. To help solve this problem, water and a phase transfer catalyst were used to replace organic solvents in the transformations of bromoacetophenones into chloroacetophenones and aroyl epoxides into aroyl chlorohydrins. The reactions were promoted by sulfonyl chlorides and gave quantitative or close to quantitative yields. Notably, chromatographic purification, which is laborious and consumes large amounts of organic solvents, was not needed. These two processes have opened a green and cost-effective channel to prepare the chemical intermediates chloroacetophenones and aroyl chlorohydrins. The reaction mechanisms are discussed based on control experiments.

Experimental study on the reaction pathway of α-haloacetophenones with NaOMe: Examination of bifurcation mechanism

The reaction of PhCOCH2Br and NaOMe in MeOH gave PhCOCH 2OH as the major product and PhCOCH2OMe as the minor product. Substituent effects on the reactivity and product selectivity revealed that an electron-withdrawing substituent on the phenyl ring enhanced the overall reactivity and gave more alcohol than ether. It was indicated that the alcohol was formed via carbonyl addition-epoxidation, whereas the ether was formed by direct substitution. Substituent effects on the reaction rates, as well as the effects of NaOMe concentration on the rate and product ratio for both reactions of PhCOCH2Br and PhCOCH2CI are in line with the mechanism that the alcohol and ether products were formed via two independent and concurrent routes, carbonyl addition and a-carbon attack, respectively, and thus the reaction mechanism could be different from the bifurcation mechanism previously predicted for the reaction of PhCOCH2Br by a simulation study in the gas phase.

Direct conversion of alcohols to α-chloro aldehydes and α-chloro ketones

Direct conversion of primary and secondary alcohols into the corresponding α-chloro aldehydes and α-chloro ketones using trichloroisocyanuric acid, serving both as stoichiometric oxidant and α-halogenating reagent, is reported. For primary alcohols, TEMPO has to be added as an oxidation catalyst, and for the transformation of secondary alcohols (TEMPO-free protocol), MeOH as an additive is essential to promote chlorination of the intermediary ketones.