108321-66-0

Basic information

• Product Name: Ethanone, 2-chloro-1-phenyl-, labeled with carbon-14 (9CI)
• Synonyms: Ethanone, 2-chloro-1-phenyl-, labeled with carbon-14 (9CI)
• CAS NO: 108321-66-0
• Molecular Formula: C8H7ClO
• Molecular Weight: 0
• Mol File: 108321-66-0.mol
• Article Data: 182

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethanone, 2-chloro-1-phenyl-, labeled with carbon-14 (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 2-chloro-1-phenyl-, labeled with carbon-14 (9CI)(108321-66-0)
• EPA Substance Registry System: Ethanone, 2-chloro-1-phenyl-, labeled with carbon-14 (9CI)(108321-66-0)

Safety Data

• Hazardous Substances Data: 108321-66-0(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 98-88-4 benzoyl chloride 
• 109538-22-9 diethyl-(1,2-dichloro-vinyl)-amine 
• 107-14-2 chloroacetonitrile 
• 94-41-7 benzalacetophenone 
• 56-23-5 tetrachloromethane 
• 624-85-1 ethyl hypochlorite 
• 98-86-2 acetophenone 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 919-24-4 tetrakis(chloroacetoxy)silane 
• 71-43-2 benzene 
• 100-42-5 styrene 
• 1194-34-9 α-chlorostyrene oxide 

Downstream Products

• 1005-91-0 2-phenyl-2-(chloromethyl)oxirane 
• 115217-25-9 2-hexahydroazocin-1-yl-1-phenyl-ethanone 
• 40327-64-8 (3-furan-2-yl-oxiranyl)-phenyl-methanone 
• 193688-13-0 2-benzoylbenzothiophene-3-carboxylic acid 
• 5399-30-4 2-oxo-2-phenylethylthiocyanate 
• 15424-12-1 1a-acetyl-1-benzoyl-1a,7b-dihydro-1H-cyclopropa[c]chromen-2-one 
• 118924-96-2 8syn-methyl-8anti-phenacyl-3endo-phenylacetoxy-nortropanium; chloride 
• 81674-25-1 2-(2-hydroxy-ethylamino)-1-phenyl-ethanone 
• 22536-48-7 2-phenacylmercapto-propionic acid 
• 950-17-4 1,1-diphenyl-2-chloroethan-1-ol 
• 20228-06-2 acetic acid N'-(4-phenyl-thiazol-2-yl)-hydrazide 
• 15561-33-8 1-chloro-2-phenylpropan-2-ol 
• 109251-86-7 1-naphtyl phenacyl sulfide 
• 4937-87-5 N-hydroxy-2-oxo-2-phenylethanimidoyl chloride 

Relevant articles and documents

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Reactions of alkynylselenonium salts with tetrabutylammonium halides: Apparent umpolung of alkynyl moiety

The reactions of alkynylselenonium salts with n-Bu4NX (X = I, Br, Cl) in CH2Cl2 gave 1-halo-1-alkynes or phenacyl halide derivatives and selenide, while the reaction with F afforded a terminal alkyne and a selenoxide. Seemingly, the selenonium salts acted as alkynyl cations in the former case and as alkynyl anions in the latter case.

Design, synthesis, & biological activity of new triazole & nitro-triazole derivatives as antifungal agents

In this study two series of fluconazole derivatives bearing nitrotriazole (series A) or piperazine ethanol (series B) side chain were designed and synthesized and then docked in the active site of lanosterol 14α-demethylase enzyme (1EA1) using the Autodock 4.2 program (The scripps research institute, La Jolla, CA, USA). The structures of synthesized compound were confirmed by various methods including elemental and spectral (NMR, CHN, and Mass) analyses. Then antifungal activities of the synthesized compound were tested against several natural and clinical strains of fungi using a broth microdilution assay against several standard and clinical fungi. Nitrotriazole derivatives showed excellent and desirable antifungal activity against most of the tested fungi. Among the synthesized compounds, 5a-d and 5g, possessing nitrotriazole moiety, showed maximum antifungal activity, in particular against several fluconazole-resistant fungi.

MONOHALOMETHYLLITHIUM XCH2Li : STABILIZATION OF A POTENTIAL SYNTHETIC REAGENT

The preparation of monohalomethyllithium XCH2Li is achieved by Bromine-lithium exchange from the corresponding Bromohalomethane in the presence of one equivalent of lithium bromide at -110 degC in THF-Ether-Pentane solutions.This reagent, on coupling with various carbonyl compounds leads to halohydrins, epoxides and α-halomethyl ketones with high yields.

α-chlorination of acetophenones using 1,3-dichloro-5,5- dimethylhydantoin

A novel method for the synthesis of α-chloroacetophenones using 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) and p-toluenesulfonic acid in methanol at 30-35°C is described. Substituted acetophenones at the para position or meta position of aromatic ring give α-chloroacetophenones in high yield. However, reaction of o-nitroacetophenone does not take place under the same condition. Copyright Taylor & Francis LLC.

Water-controlled selective preparation of α-mono or α,α′-dihalo ketones: Via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin

The control of a reaction that can produce multiple products from the same starting material is a highly attractive and challenging concept in organic synthesis. An efficient protocol for the selective synthesis of α-mono or α,α′-dihalo ketones via a water-controlled three-component thiourea-catalyzed cascade reaction of unactivated alkynes, 1,3-dihalo-5,5-dimethylhydantoin and water has been developed. α-Monohaloketones were obtained in aqueous acetone at 45 °C; conversely, α,α′-dihalo ketones were formed with pure water as the sole solvent at room temperature.

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Indirect electrooxidation of halohydrins by a double mediatory system of Ru(VIII)/Ru(IV) and [Cl+]/Cl-. Optimization for the oxidation of 1,3-dichloro-2-propanol to 1,3-dichloroazcetone

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Electrophilicities of α-chlorinating agents used in organocatalysis

Kinetics of the reactions of the chlorinating agents 1a-c with π-nucleophiles have been studied to include these compounds in our comprehensive electrophilicity scale.

InCl3: A new Lewis acid catalyst for reactions with α-diazocarbonyl compounds

The use of InCl3 as a Lewis acid catalyst in diazocarbonyl S-H insertion reactions, nitrile cyclizations and addition reactions to aldehydes and ketones is described.

The Mn-catalyzed paired electrochemical facile oxychlorination of styrenes: Via the oxygen reduction reaction

Reported herein is the electrochemical engendering of chlorine radicals by a manganese catalyst with a controllable pattern, and inexpensive MgCl2 as the chlorine source. In combination with the oxygen reduction reaction, chloroacetophenones were synthesized with abundant styrene as the feedstock in good to excellent yields.

Preparation of α-Chloro Ketones from Enol Silyl Ethers with Sulfuryl Chloride Fluoride and Sulfuryl Chloride

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α-Chlorination of Aromatic Acetyl Derivatives with Benzyltrimethylammonium Dichloroiodate

Reaction of aromatic acetyl derivatives with benzyltrimethylammonium dichloroiodate in refluxing dichloroethane/methanol for several hours gave α-chloroacetyl derivatives in good yields.

A convenient and efficient synthesis of 1-aryl-2,2-dichloroethanones

1-Arylethanones are readily chlorinated with an aqueous HCl-H 2O2 system using ethanol as a cosolvent. The reaction prceeds rapidly and results in selective conversion of 1-arylethanones into 1-aryl-2,2-dichloroethanones in yields of 48-89%, depending on the nature of the substituent in the aryl group.

Efficient α-chlorination and α-bromination of carbonyl compounds using N-halosuccinimides/UHP in ionic liquid

A facile and efficient method for the α-halogenation of carbonyl compounds utilizing N-halosuccinimides (NXS) in the presence of urea-hydrogen peroxide (UHP) in [bmim]BF4 has been newly developed. Copyright Taylor & Francis Group, LLC.

Indium(I) bromide mediated coupling of α,α-dichloroketones with carbonyl compounds in aqueous media: The preparation of 2-chloro-3- hydroxypropan-1-one derivatives

Indium(I) bromide promotes the reductive coupling of α,α- dichloroketones with carbonyl compounds to the corresponding 2-chloro-3-hydroxypropan-1-one derivatives in moderate to good yields. Georg Thieme Verlag Stuttgart.

Continuous flow generation and reactions of anhydrous diazomethane using a teflon AF-2400 tube-in-tube reactor

A continuous process for generation, separation, and reactions of anhydrous diazomethane in a tube-in-tube reactor was developed. The inner tube of the reactor is made of hydrophobic, gas-permeable Teflon AF-2400. The diazomethane is formed in the inner tube and then diffuses through the permeable membrane into the outer chamber and subsequently reacts in the solution carried within. This technique allows safe and scalable reactions with dry diazomethane to be performed on a laboratory scale.

Vanadium-catalyzed chlorination under molecular oxygen

A catalytic chlorination of ketones was performed by using a vanadium catalyst in the presence of Bu4NI and AlCl3 under atmospheric molecular oxygen. This catalytic chlorination could be applied to the chlorination of alkenes to give the corresponding vic-dichlorides. AlCl3 was found to serve as both a Lewis acid and a chloride source to induce the facile chlorination. A combination of Bu4NI and AlI3 in the presence of a vanadium catalyst under atmospheric molecular oxygen induced the iodination of ketones.

A simple, mild, and efficient method for the preparation of α,α-dichloroketones with DCDMH catalyzed by ammonium chloride

New process that can selectively prepare α,α-dichloro ketones from various ketones with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) using ammonium chloride as a catalyst is reported. The effects of ammonium salts, solvents, DCDMH, and reaction temperature were investigated. Under the optimal condition, most of α,α-dichlorinated products were selectively obtained in 86-98% yield.

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Gold-catalyzed hydration of haloalkynes to α-halomethyl ketones

A general atom-economical approach for the synthesis of α-halomethyl ketones is demonstrated through hydration of a wide range of haloalkynes. Other outstanding features include excellent yields from both alkyl- and aryl-substituted haloalkynes and wide functional group tolerance. This protocol is an alternative to conventional α-halogenation of ketones.

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.

A mild, convenient, and inexpensive procedure for conversion of vinyl halides to α-haloketones

Treatment of a vinyl chloride with commercially available aqueous sodium hypochlorite solution in a 2:5 mixture of acetic acid/acetone at 0 °C for about 1 h cleanly leads to the corresponding α-chloroketone. Similarly, if a vinyl bromide is exposed to sodium hypobromite (freshly prepared from bromine and sodium hydroxide) at 0 °C in 2:5 acetic acid/acetone as solvent, an α-bromoketone is produced. This methodology has been applied to a number of vinyl chlorides and vinyl bromides, and the transformations generally proceed in high yields. The mild reaction conditions are compatible with a variety of functional groups including amides, esters, and imines.

Transition metal-catalyzed oxidations. 12 : α-Chlorination of silylenol ethers with tert-butyl hydroperoxide and TiCl2(OiPr)2

Enolsilyl ethers (4, 6, 8, 10, 12, 14) are chlorinated to the α-monochloro ketones (5, 7, 9, 11, 13, 15) with tert-butyl hydroperoxide in the presence of dichlorotitanium diisopropoxide in 69 - 92% yield. WILEY-VCH Verlag GmbH, 1999.

Straightforward Synthesis of α-Chloromethylketimines Catalyzed by Gold(I). A Clean Way to Building Blocks

α-Chloromethylketimines have been obtained through a gold-catalyzed hydroamination of aromatic and aliphatic 1-chloroalkynes with aromatic amines by using equimolar amounts of both reagents. This procedure has allowed the preparation and spectroscopic characterization of α-chloromethylketimines for the first time with a high degree of purity, complete conversion, and atom economy. The synthetic usefulness of the methodology has been demonstrated with the preparation of β-chloroamines and indoles.

Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride

Pentafluorosulfanyl chloride (SF5Cl) is the most prevalent reagent for the incorporation of SF5 group into organic compounds. However, the preparation of SF5Cl often relies on hazardous reagents and specialized apparatus. Herein, we described a safe and practical synthesis of a bench-stable and easy-to-handle solution of SF5Cl in n-hexane under gas-reagent-free conditions. The synthetic application of SF5Cl was demonstrated through the unprecedented reaction with diazo compounds. The chemoselective hydro- and chloropentafluorosulfanylations of α-diazo carbonyl compounds were developed in the presence of K3PO4 or copper catalyst, respectively. These reactions provide a direct and efficient access to various α-pentafluorosulfanyl carbonyl compounds of high value for potential applications.