1016-78-0

Basic information

• Product Name: (3-Chlorophenyl)(phenyl)methanone
• Synonyms: Benzophenone, 3-chloro-;LABOTEST-BB LT00159867;M-CHLOROBENZOPHENONE;(3-CHLOROPHENYL)(PHENYL)METHANONE;3-CHLOROBENZOPHENONE;3-CHLOROBENZOPHENONE 97%;3-Chlorobenzophenone, 99+%;3-CHLOROBENZOPHENONE=99.0%
• CAS NO: 1016-78-0
• Molecular Formula: C₁₃H₉ClO
• Molecular Weight: 216.66
• EINECS: 213-809-0
• Product Categories: Aromatic Benzophenones & Derivatives (substituted)
• Mol File: 1016-78-0.mol
• Article Data: 85

Chemical Properties

• Melting Point: 85-87 °C(lit.)
• Boiling Point: 332°C(lit.)
• Flash Point: 178.3 °C
• Appearance: White to off-white amorphous powder
• Density: 1.1459 (rough estimate)
• Vapor Pressure: 9.39E-05mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Store below +30°C.
• BRN: 1869822
• CAS DataBase Reference: (3-Chlorophenyl)(phenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (3-Chlorophenyl)(phenyl)methanone(1016-78-0)
• EPA Substance Registry System: (3-Chlorophenyl)(phenyl)methanone(1016-78-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36/37/39-22-36
• WGK Germany: 3
• Hazardous Substances Data: 1016-78-0(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO OFF-WHITE AMORPHOUS POWDER

Uses

3-Chlorobenzophenone is a reagent in the preparation of pharmaceuticals such as antitumor kinesin spindle protein inhibitors.

InChI:InChI=1/C13H9ClO/c14-12-8-4-7-11(9-12)13(15)10-5-2-1-3-6-10/h1-9H

Upstream product

• 861532-09-4 1,2-bis(3-chlorophenyl)-1,2-diphenylethane-1,2-diol 
• 103-73-1 Phenetole 
• 63012-03-3 3-chlorobenzhydrol 
• 618-46-2 m-Chlorobenzoyl chloride 
• 71-43-2 benzene 
• 36967-85-8 benzoyl triflate 
• 108-90-7 chlorobenzene 
• 25116-37-4 3-iodobenzophenone 
• 625-99-0 3-iodochlorobenzene 
• 98-88-4 benzoyl chloride 
• 108-37-2 1-bromo-3-chlorobenzene 
• 63503-60-6 3-chlorophenylboronic acid 
• 65-85-0 benzoic acid 
• 535-80-8 3-chlorobenzoate 

Downstream Products

• 55095-14-2 [1-phenyl-1-(3-chlorophenyl)methyl]amine 
• 63012-03-3 3-chlorobenzhydrol 
• 2999-00-0 3-chloro-benzophenone-seqcis-oxime 
• 3136-53-6 3-chloro-benzophenone-seqtrans-oxime 
• 861532-09-4 1,2-bis(3-chlorophenyl)-1,2-diphenylethane-1,2-diol 
• 72754-68-8 7-[2-(3-chloro-benzhydrylamino)-ethyl]-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 119870-88-1 3-chlorobenzophenone 4-methylphenylsulfonylhydrazone 
• 127568-33-6 N-(m-chlorobenzhydryl)formamide 
• 14161-68-3 1-Chloro-3-(2-methyl-1-phenyl-propenyl)-benzene 
• 1027382-45-1 3-carbethoxy-4-phenyl-4-(3-chlorophenyl)but-3-enoic acid 
• 65-85-0 benzoic acid 
• 535-80-8 3-chlorobenzoate 
• 108-90-7 chlorobenzene 
• 93532-39-9 (3-chlorophenyl)phenylmethanone oxime 

Relevant articles and documents

A Convenient Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Halides with Formic Acid as the Carbon Monoxide Source

A practical palladium-catalyzed carbonylative Suzuki coupling of aryl halides under carbon monoxide gas-free conditions has been developed. Here, formic acid was utilized as the carbon monoxide source for the first time with acetic anhydride as the additive. A variety of diarylketones were produced in moderate to excellent yields from the corresponding aryl halides and arylboronic acids.

Convenient Stille carbonylative cross-couplings using molybdenum hexacarbonyl

Palladium catalysis was used in Stille-type carbonylative cross-couplings employing Mo(CO)6 as the carbon monoxide source. Robust and convenient transformations were carried out in closed vessels at 100 °C, providing a set of diaryl ketones in good yields. Aryl triflates and bromides were used as coupling partners with aryl stannanes. Inclusion of the Mo(CO)6 destabilizing agent DBU made this protocol operationally simple and suppressed side-product formation.

Substituent modulation of mild fluorination of aromatic molecules with caesium fluoroxysulphate

Functionalization of mono- and di-substituted benzene derivative with CsSO4F has been modulated by substituents on the benzene ring. α-Hydroxyalkylbenzenes, with a deactivated ring, were oxidized to phenones, while fluorodealkylation was achieved in high yield when electron-donating groups were present in a para position. Electron-withdrawing substituents favoured chain fluorofunctionalization in alkylbenzenes, while ring fluorination was found exclusively in acylamino-derivatized alkylbenzenes; fluoro-addition products were formed in the case of p-alkoxy-substituted alkylbenzene derivatives.

Pd(II)-Catalyzed decarboxylative cross-coupling of potassium aryltrifluoroborates with α-oxocarboxylic acids at room temperature

A novel Pd-catalyzed decarboxylative cross-coupling of potassium aryltrifluoroborates with R-oxocarboxylic acids is performed at room temperature. This reaction provides an efficient access to aryl ketones under mild conditions.

Pd-catalyzed synthesis of functionalized arylketones from boronic acids and carboxylic acids activated in situ with dimethyl dicarbonate

Highly efficient catalyst systems were developed that allow the palladium-catalyzed cross-coupling of arylboronic acids with carboxylic acids activated in situ with dimethyl dicarbonate at room temperature. As byproducts, only methanol, CO2, an

Carbonylative Hiyama coupling of aryl halides with arylsilanes under balloon pressure of CO

An efficient protocol has been developed for the carbonylative Hiyama coupling of aryl halides using the cesium fluoride as a promoter by palladium-catalyzed in NMP. This protocol was applied to a wide variety of functionalized and hindered aryl iodides and bromides with arylsilanes, to afford the desired biaryl ketones in good to excellent yields.

Copper-catalyzed aerobic synthesis of bisaryl ketones from alkynes via the cleavage of C-C triple bonds

A novel copper-catalyzed aerobic synthesis of bisaryl ketones from 1,2-diarylalkynes via the cleavage of C-C triple bonds is reported. This reaction is a new transformation of 1,2-diarylalkynes into bisaryl ketones.

Palladacycle-catalyzed cross-coupling reactions of arylboronic acids with carboxylic anhydrides or acyl chlorides

The triphenylphosphine-cyclopalladated ferrocenylimine (Cat. 2) exhibited highly catalytic activity for the both of arylboronic acids with carboxylic anhydrides and acyl chlorides with low catalyst loading (0.5 mol %). The reactions were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic derivatives. Up to 98% yield was obtained for 32 examples. However, they were limited for arylboronic acid with strong electron-withdrawing groups. It is noting that catalyst 2 can be reused for eight times without losing its catalytic activity.

Novelmeta-benzothiazole and benzimidazole functionalised POCOP-Ni(ii) pincer complexes as efficient catalysts in the production of diarylketones

The synthesis of four novel non-symmetric Ni(ii)-POCOP pincer complexesmeta-functionalized with either benzothiazole or benzimidazole at the central aryl ring is described. All complexes were fully characterised in solution by various analytical techniques and the molecular structures in the solid state of complexes1b,2aand2bwere unequivocally determined by single crystal X-ray diffraction analysis. In addition, the Ni(ii)-POCOP pincer complexes were efficiently used as catalysts in the synthesis of diarylketones by cross-coupling reactions of functionalized benzaldehydes and boronic acid derivatives under relatively mild conditions. An important aspect of this transformation is the dependence on the steric properties of the donor groups (OPR2) of the pincer ligands, the more active compounds having the phosphinitos bearing isopropyl groups (1aand2a) than those containingtert-butyl substituents (1band2b).

Photoinduced Radical Cleavage of Iodobenzophenones

The triplet state cleavage of m-iodo-(mibp) and p-iodobenzophenone (pIBP) to benzoylphenyl and iodine radicals has been studied by both steady state and laser flash techniques.Phosphorescence spectra in methanol/ ethanol glasses at 77 K indicate triplet energies of 68.4 and 67.8 kcal/mol for mIBP and pIBP, respectively.In most organic solvents products are benzophenone and iodinated solvents; these are formed by hydrogen abstraction from solvent by the initially formed benzoylphenyl radicals.Quantum yields for product formation decrease with increasing solvent viscosity, ranging from 0.45 in acetonitrile to 0.28 in cyclopentane and 0.05 in cyclooctane; they appear to reflect significant in-cage recoupling of the initial radical pairs.Quenching of the reaction by naphthalene indicates 25 degC triplet lifetimes of 25 and 0.2 ns for mIBP and pIBP, respectively, which were confirmed by flash kinetics.Laser excitation produced transient signals assigned to the iodine atom-toluene complex (in toluene) and, for mIBP, the triplet ketone.Decay of the latter revealed activation parameters ΔH = 4.0 +/- 0.2 kcal/mol and log A = 10.6 +/- 0.2 for mIBP in both methanol and toluene.The strong phosphorescence of both ketones at 77 K indicates that ΔH for pIBP must be >= 3kcal/mol, such that log A is ca. 12, much higher than for mIBP.The different rates and A values reflect different ?* spin densities at the meta and para positions in the lowest n,?* triplets, which react either by mixing with dissociative ?,?* states or by thermally converting into a dissociative ?,?* or ?1,?* state.The dependence of ?* spin density and the low A values strongly suggest an inefficient state interconversion at a surface crossing between n,?* and ?,?* states, because of their different symmetries.It is suggested that the low A values, which might indicate negative Δs values, are better understood as low transmission coefficients.

Palladium on magnetic Irish moss: A new nano-biocatalyst for suzuki type cross-coupling reactions

A novel heterogeneous magnetic palladium nano-biocatalyst was designed by utilizing Irish moss, a family of sulfated polysaccharides extracted from algae, as a natural biopolymer. This magnetic Irish moss decorated with palladium (Pd–Fe3O4@IM) to form a biomagnetic catalytic system was synthesized and well characterized by FT–IR analysis, X-ray powder diffraction, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, atomic absorption spectroscopy and transmission electron microscopy. The catalyst was stable to air and moisture and displayed high catalytic activity in ligand-free Suzuki–Miyaura cross-coupling reactions conducted under green chemistry reaction conditions. The aromatic ketones are produced by the cross-coupling reaction between acid chlorides and aryl boronic acid derivatives in high yields.

A new convenient procedure to prepare organomanganese reagents from organic halides and activated manganese

A new method to obtain activated manganese metal, especially attractive for large scale preparative organic chemistry, is described. The key point is the use of 2-phenylpyridine as electron carrier to reduce manganese chloride by lithium. The active manganese thus obtained was used to prepare various organomanganese reagents from organic halides. The reactivity of these reagents has been studied (acylation, 1,2- or 1,4-addition, alkylation and alkenylation).

Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design

A series of diaryl ketones have been synthesized in moderate to excellent yields through the selective cross-coupling reaction of benzoyl chlorides with arylstannanes using a sonochemical variation of the Stille coupling. Ultrasound significantly enhances this useful organometallic transformation affording the desired products in higher yields and shorter reaction times than conventional reactions. The scope of the protocol has been explored with a selection of arylstannanes and different aroyl chlorides as reaction partners. Remarkably, no by-products resulting from homo-coupling could be detected. The ultrasound-promoted cross-coupling reaction was optimized through experimental design.

Fe-S Catalyst Generated in Situ from Fe(III)- And S3?--Promoted Aerobic Oxidation of Terminal Alkenes

An iron-sulfur complex formed by the simple mixture of FeCl3 with S3?- generated in situ from K2S is developed and applied to selective aerobic oxidation of terminal alkenes. The reaction was carried out under an atmosphere of O2 (balloon) and could proceed on a gram scale, expanding the application of S3?- in organic synthesis. This study also encourages us to explore the application of an Fe-S catalyst in organic reactions.

Cesium hydroxide-promoted aerobic oxidation of sec-aromatic alcohols

A CsOH-promoted aerobic oxidation of sec-aromatic alcohols has been developed, using air as a free and clean oxidant, and providing aryl ketones in good to excellent yields.

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An efficient and recyclable thermoregulated phosphine-palladium catalyst for the carbonylative Suzuki coupling of aryl halides with arylboronic acids in water

An efficient protocol has been developed for the carbonylative Suzuki coupling of aryl halides using the thermoregulated phosphine-palladium as a reusable catalyst in pure water. This protocol was applied to a wide variety of hindered and functionalized aryl iodides and bromides with arylboronic acids, to afford the desired biaryl ketones in good to high yields. The palladium catalyst was easily recovered in the aqueous phase and reused up to eight cycles without a significant decrease in its activity.

Supported Palladium-Catalyzed Carbonylative Synthesis of Diaryl Ketones from Aryl Bromides and Arylboronic Acids

A palladium supported on graphitic carbon nitride (Pd/g-C3N4) catalyzed carbonylative reaction of aryl bromides and arylboronic acids by has been developed for the construction of diaryl ketones. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source, the reaction proceeded well to give various diaryl ketones in moderate to good yields.

Copper/palladium-cocatalyzed aerobic synthesis of bisaryl ketones from Olefins via C-C double bonds cleavage

A novel palladium/copper-catalyzed aerobic synthesis of bisaryl ketones from 1,2-diarylalkenes via C-C double bonds cleavage has been described. This reaction constitutes a new transformation from 1,2-diarylalkenes into bisaryl ketones, providing a unifying, simple and environmentally friendly complement to the available methods.

Nickel-catalyzed diaryl ketone synthesis by N-C cleavage: Direct negishi cross-coupling of primary amides by site-selective N,N-Di-boc activation

A general Negishi acylation of primary amides enabled by a combination of site-selective N,N-di-Boc activation and nickel catalysis is reported for the first time. The reaction is promoted by a bench-stable, inexpensive Ni catalyst. The reaction shows excellent functional group compatibility, affording functionalized diaryl ketones by selective N-C cleavage. Most notably, this protocol represents the first amide cross-coupling by direct metal insertion of simple and readily available primary amides. The overall strategy by N,N-di-Boc activation/metal insertion is suitable for a broad range of coupling protocols via acylmetals. Mechanistic experiments suggest high reactivity of N,N-di-Boc activated 1° amides in direct amide C-N cross-couplings.

Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage

Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe

Photo-induced oxidative cleavage of C-C double bonds of olefins in water

The carbonyl compounds, synthesized by the oxidative cleavage of their corresponding olefins, are of great significance in organic synthesis, especially aryl ketones. We have developed a gentle and effective protocol, using acid red 94 as the organic metal-free photocatalyst, O2 as the oxidant, and water as the solvent. Under visible light irradiation, aryl ketone derivatives were obtained in moderate to excellent yields, showing good economic and environmental advantages.