Conditions | Yield |
---|---|
With aluminium trichloride for 19.5h; Heating; | 100% |
Friedel-Crafts reaction; | 90% |
iron(III) chloride at 109℃; for 0.458333h; Product distribution / selectivity; Irradiation; | 83% |
(2-chlorophenyl)phenylmethanone oxime
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; for 0.0166667h; neat (no solvent); | 98% |
With periodic acid at 20℃; for 0.3h; | 86% |
Conditions | Yield |
---|---|
With C4F9SO3H at 130℃; for 0.333333h; Product distribution; var. of time, conc. of reagent; | 96% |
With aluminum (III) chloride for 6h; Friedel-Crafts Acylation; Reflux; |
sodium tetraphenyl borate
o-chlorobenzoyl chloride
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With potassium fluoride; bis-triphenylphosphine-palladium(II) chloride In acetone for 0.15h; microwave irradiation (525 W); | 94% |
With aluminum oxide; bis-triphenylphosphine-palladium(II) chloride; potassium fluoride In acetone for 0.0833333h; MW-irradiation; | 90% |
With silica-supported diphenylphosphine palladium(0) In tetrahydrofuran at 40℃; for 48h; | 74% |
(2-chlorophenyl)(phenyl)methanol
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With cobalt(III) acetate; sodium bromide In acetic acid at 60℃; for 1h; | 93% |
With peracetic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In acetonitrile at 20℃; for 9h; | 93% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 80℃; for 0.5h; Reagent/catalyst; | 92% |
(o-benzyl)chlorobenzene
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With pyridine; tert.-butylhydroperoxide; iodine In water at 80℃; chemoselective reaction; | 93% |
With N-Bromosuccinimide; water In chloroform for 3h; Reflux; | 92% |
With lithium perchlorate In water; acetonitrile at 20℃; for 5h; Electrolysis; | 67% |
2-Chlorobenzeneboronic acid
benzoyl chloride
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With 2C60H80NaO12(2+)*Cl6Pd2(2-); potassium carbonate; triphenylphosphine In toluene at 70℃; for 12h; Suzuki Coupling; | 93% |
With [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)]; potassium carbonate In toluene at 60℃; for 12h; Inert atmosphere; | 90% |
1-(o-chlorophenyl)-1-phenylethylene
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With oxygen at 110℃; for 8h; Schlenk technique; Green chemistry; | 91% |
With oxygen at 110℃; for 8h; Sealed tube; | 90.9% |
With cerium(III) chloride; 1,1,1-trichloroethanol In acetonitrile at 25℃; for 40h; Irradiation; | 78% |
Conditions | Yield |
---|---|
With sodium periodate; tetraethylammonium iodide In water; acetonitrile at 105℃; for 12h; Sealed tube; | 89% |
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; under 760.051 Torr; for 6h; Hiyama Coupling; | 88% |
2-Chlorobenzeneboronic acid
Benzoylformic acid
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With silver carbonate In acetonitrile at 60℃; for 1h; | 87% |
carbon monoxide
Phenyl triflate
2-Chlorobenzeneboronic acid
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium(II) trifluoroacetate In tert-butyl methyl ether at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling; | 87% |
Conditions | Yield |
---|---|
With copper(l) iodide; palladium(II) iodide at 120℃; for 3h; | 85% |
ortho-chlorobenzoic acid
phenylboronic acid
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); water; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 60℃; for 15h; Inert atmosphere; | 84% |
2-Chlorobenzeneboronic acid
benzaldehyde
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With [Pd(2-((1-naphthalenyl)methylene)-N-phenylhydrazinecarbothioamide)Cl(PPh3)]; caesium carbonate In toluene at 110℃; for 12h; | 84% |
With potassium phosphate; 3,3-dimethyl-butan-2-one; C14H10Cl2N2O2Ru; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 100℃; for 24h; | 65% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; N-chloro-succinimide; trifluorormethanesulfonic acid; palladium diacetate In 1,2-dichloro-ethane at 80℃; for 10h; Reagent/catalyst; | 83% |
carbon monoxide
2-iodochlorobenzene
triethoxyphenylsilane
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; under 760.051 Torr; for 6h; Hiyama Coupling; | 83% |
carbon monoxide
toluene-4-sulfonic acid phenyl ester
2-Chlorobenzeneboronic acid
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl acetamide at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling; | 83% |
2-chloro-benzaldehyde
phenylboronic acid
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With [Pd(2-((1-naphthalenyl)methylene)-N-phenylhydrazinecarbothioamide)Cl(PPh3)]; caesium carbonate In toluene at 110℃; for 12h; | 83% |
With C36H28NO2PPd; caesium carbonate In toluene for 18h; Reagent/catalyst; Reflux; | 79% |
o-chlorobenzoyl chloride
phenylboronic acid
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With potassium carbonate; (t-Bu2POH)2PdCl2 In 1,4-dioxane; toluene at 80℃; for 1h; Suzuki cross-coupling reaction; | 82% |
With water; sodium carbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; palladium diacetate at 60℃; for 3h; Suzuki reaction; | 80% |
With C28H40Br4N4Pd2; potassium carbonate In ethanol; water at 50℃; for 5h; Suzuki Coupling; | 78% |
With sodium dodecyl-sulfate; potassium carbonate; palladium dichloride In water at 60℃; for 6h; | 40% |
2-chlorobenzoic anhydride
phenylboronic acid
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With PEG200; sodium carbonate; palladium diacetate at 60℃; for 3h; Suzuki reaction; | 82% |
With sodium carbonate; palladium dichloride In water; acetone at 20℃; for 1.5h; Suzuki type reaction; Inert atmosphere; | 78% |
With sodium dodecyl-sulfate; potassium carbonate; palladium dichloride In water at 60℃; for 6h; | 68% |
N-amino-o-chlorobenzenesulfonamide
benzonitrile
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With 2,2'-biquinoline; water; palladium diacetate In dimethyl sulfoxide at 80℃; under 760.051 Torr; for 6h; | 82% |
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; under 760.051 Torr; for 6h; Hiyama Coupling; | 81% |
o-(α,α-dichlorobenzyl)phenyl phosphochloridate
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With trichlorophosphate at 220℃; under 1 Torr; | 80% |
phenylglyoxylic acid potassium salt
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver nitrate In water at 25℃; for 1h; Green chemistry; | 79% |
carbon monoxide
2-iodochlorobenzene
benzene
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 100℃; under 3040.2 Torr; for 24h; Inert atmosphere; Sealed tube; Glovebox; Schlenk technique; Green chemistry; chemoselective reaction; | 79% |
(2-Chloro-phenyl)-phenyl-methanethione
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With clay supported ferric nitrate; Clayfen In dichloromethane for 8h; Ambient temperature; | 78% |
2-bromo-1-chlorobenzene
carbon monoxide
triethoxyphenylsilane
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; under 760.051 Torr; for 6h; Hiyama Coupling; | 78% |
Conditions | Yield |
---|---|
With phosphorus pentachloride at 215 - 220℃; | 77.2% |
(2-chlorophenyl)(phenyl)methanone
(2-chlorophenyl)(phenyl)methanol
Conditions | Yield |
---|---|
With N-methylpyrrolidine zinc borohydride In tetrahydrofuran for 0.5h; Heating; | 100% |
With [(OC-6-13)-RuCl2[P(p-CH3C6H5)3]2(en)]; potassium tert-butylate; hydrogen In isopropyl alcohol; tert-butyl alcohol at 28℃; under 6080.41 Torr; for 12h; Catalytic hydrogenation; | 95% |
With sodium tetrahydroborate In ethanol at 20℃; for 3h; | 94.1% |
(2-chlorophenyl)(phenyl)methanone
(S)-2-chlorobenzhydrol
Conditions | Yield |
---|---|
Stage #1: (2-chlorophenyl)(phenyl)methanone With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; polymethylhydrosiloxane; copper(l) chloride; sodium t-butanolate In toluene at -30℃; for 13h; Inert atmosphere; Stage #2: With sodium hydroxide; water In ethyl acetate; toluene for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
With formic acid; ((R,R)-Ts-DENEB)RuCl; triethylamine at 40℃; for 17h; Reagent/catalyst; Inert atmosphere; enantioselective reaction; | 99% |
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; enantioselective reaction; | 99% |
(2-chlorophenyl)(phenyl)methanone
p-tolylzinc(II) chloride
(4′-methylbiphenyl-2-yl)(phenyl)methanone
Conditions | Yield |
---|---|
With C26H24ClN2NiP*0.1C7H8 In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Negishi Coupling; Schlenk technique; Inert atmosphere; | 99% |
With Ni(Cl){2-(Ph2P(O))C6H4NCH(Ph)PPh2} In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 25℃; for 24h; Negishi coupling reaction; Inert atmosphere; | 98% |
With C27H22Cl2N3NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 24h; Inert atmosphere; Schlenk technique; Heating; | 91% |
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C43H53FeN2O2PS; hydrogen; lithium tert-butoxide In isopropyl alcohol at 25 - 30℃; under 22801.5 Torr; for 12h; Autoclave; enantioselective reaction; | 98% |
With potassium tert-butylate; hydrogen; triphenylphosphine In toluene; tert-butyl alcohol at 25℃; under 15201 Torr; for 24h; Product distribution / selectivity; | 95% |
With hydrogen; C34H63ClIrNP2; lithium tert-butoxide In hexane; toluene at 20℃; under 38002.6 Torr; for 24h; Autoclave; enantioselective reaction; | 95% |
(2-chlorophenyl)(phenyl)methanone
4-methoxyphenyl magnesium bromide
(4′-methoxylbiphenyl-2-yl)(phenyl)methanone
Conditions | Yield |
---|---|
Stage #1: 4-methoxyphenyl magnesium bromide In tetrahydrofuran at -20℃; for 0.166667h; Stage #2: (2-chlorophenyl)(phenyl)methanone With para-fluorostyrene; tetra-(n-butyl)ammonium iodide; cobalt acetylacetonate In tetrahydrofuran; 1,2-dimethoxyethane at 25℃; for 1h; | 98% |
Stage #1: 4-methoxyphenyl magnesium bromide In tetrahydrofuran at -20℃; for 0.166667h; Stage #2: (2-chlorophenyl)(phenyl)methanone With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; para-fluorostyrene; tetra-(n-butyl)ammonium iodide; cobalt acetylacetonate In tetrahydrofuran; 1,2-dimethoxyethane at 25℃; for 1h; Further stages.; | 98% |
(2-chlorophenyl)(phenyl)methanone
para-bromotoluene
(4′-methylbiphenyl-2-yl)(phenyl)methanone
Conditions | Yield |
---|---|
Stage #1: para-bromotoluene With lithium Stage #2: With zinc(II) chloride Stage #3: (2-chlorophenyl)(phenyl)methanone; nickel amido phosphine pincer complex In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Negishi cross-coupling; Further stages.; | 98% |
(2-chlorophenyl)(phenyl)methanone
(4-(trifluoromethyl)phenyl)zinc(II) chloride
Conditions | Yield |
---|---|
With C26H24ClN2NiP*0.1C7H8 In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Negishi Coupling; Schlenk technique; Inert atmosphere; | 98% |
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With Li2CoCl4; sodium formate In tetrahydrofuran at 25℃; Negishi Coupling; Inert atmosphere; Schlenk technique; | 98% |
trifluoromethan
(2-chlorophenyl)(phenyl)methanone
2,2,2-trifluoro-1-(2-chlorophenyl)-1-phenylethanol
Conditions | Yield |
---|---|
Stage #1: trifluoromethan; (2-chlorophenyl)(phenyl)methanone With tris(trimethylsilyl)amine; phosphazene base-P4-tert-butyl In tetrahydrofuran at 20℃; for 10h; Schlenk technique; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Schlenk technique; | 98% |
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; under 750.075 Torr; for 0.000138889h; Flow reactor; | 74% |
Conditions | Yield |
---|---|
Stage #1: 3-cyanobromobenzene With TurboGrignard In tetrahydrofuran at 0℃; for 3h; Stage #2: In tetrahydrofuran at -20℃; for 0.166667h; Stage #3: (2-chlorophenyl)(phenyl)methanone With para-fluorostyrene; tetra-(n-butyl)ammonium iodide; cobalt acetylacetonate In tetrahydrofuran; 1,2-dimethoxyethane at 25℃; for 1.5h; | 96% |
Conditions | Yield |
---|---|
Stage #1: phenylmagnesium bromide In tetrahydrofuran at -20℃; for 0.166667h; Stage #2: (2-chlorophenyl)(phenyl)methanone With para-fluorostyrene; tetra-(n-butyl)ammonium iodide; cobalt acetylacetonate In tetrahydrofuran; 1,2-dimethoxyethane at 25℃; for 0.25h; | 95% |
Conditions | Yield |
---|---|
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; para-fluorostyrene; tetra-(n-butyl)ammonium iodide; cobalt acetylacetonate In tetrahydrofuran; 1,2-dimethoxyethane at 25℃; for 0.25h; | 95% |
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In toluene at 20℃; for 0.25h; Inert atmosphere; | 95% |
(2-chlorophenyl)(phenyl)methanone
butyl magnesium bromide
(2-butyl-phenyl)-phenyl-methanone
Conditions | Yield |
---|---|
Stage #1: butyl magnesium bromide With lithium chloride; manganese(ll) chloride In tetrahydrofuran at -10℃; Stage #2: (2-chlorophenyl)(phenyl)methanone In tetrahydrofuran at -5℃; for 0.75h; | 94% |
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With N-Methyldicyclohexylamine; [iridium(2-(4-fluorophenyl)pyridinato)2(2,2'-bipyridine)]hexafluorophosphate; water-d2; lithium carbonate In acetonitrile Irradiation; | 94% |
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With chromium dichloride In tetrahydrofuran at 25℃; for 0.25h; Inert atmosphere; | 93% |
(2-chlorophenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With Li2CoCl4; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; 1,4-dioxane at 20℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; | 93% |
(2-chlorophenyl)(phenyl)methanone
para-methylphenylmagnesium bromide
A
(4,4'-dimethyl-1,1'-biphenyl)
B
(4′-methylbiphenyl-2-yl)(phenyl)methanone
Conditions | Yield |
---|---|
With C80H88Cl2N6NiP2; water; lithium chloride; zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 55℃; Kumada coupling reaction; Inert atmosphere; | A n/a B 92% |
(2-chlorophenyl)(phenyl)methanone
phenylmagnesium bromide
2-phenylbenzophenone
Conditions | Yield |
---|---|
Stage #1: phenylmagnesium bromide With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: (2-chlorophenyl)(phenyl)methanone With tributylphosphine; cobalt(II) chloride In tetrahydrofuran at 20℃; Inert atmosphere; chemoselective reaction; | 92% |
Stage #1: (2-chlorophenyl)(phenyl)methanone With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran; toluene Kumada Cross-Coupling; Inert atmosphere; Sealed tube; Stage #2: phenylmagnesium bromide In tetrahydrofuran; toluene at 20℃; for 2h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube; chemoselective reaction; | 82% |
Conditions | Yield |
---|---|
With W-7 Raney-Nickel In ethanol for 6h; Heating; | 91% |
(2-chlorophenyl)(phenyl)methanone
(3-dimethylaminopropyl)-triphenylphosphoniumbromide
Conditions | Yield |
---|---|
Stage #1: (3-dimethylaminopropyl)-triphenylphosphoniumbromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Wittig reaction; Stage #2: (2-chlorophenyl)(phenyl)methanone In tetrahydrofuran; hexane at 0 - 20℃; Further stages.; | 91% |
Conditions | Yield |
---|---|
Stage #1: phenyllithium With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: (2-chlorophenyl)(phenyl)methanone With tributylphosphine; cobalt(II) chloride In tetrahydrofuran at 20℃; Inert atmosphere; chemoselective reaction; | 91% |
Structure of 2-Chlorobenzophenone (CAS NO.5162-03-8):
IUPAC Name: (2-Chlorophenyl)-phenylmethanone
Molecular Formula: C13H9ClO
Molar mass: 216.663 g/mol
Density: 1.207 g/cm3
Flash Point: 175.2 °C
Index of Refraction: 1.594
Melting Point: 44-47 °C(lit.)
Boiling Point: 330.6 °C at 760 mmHg
Vapour Pressure: 0.000164 mmHg at 25 °C
XLogP3: 4
H-Bond Acceptor: 1
Rotatable Bond Count: 2
Exact Mass: 216.034193
MonoIsotopic Mass: 216.034193
Topological Polar Surface Area: 17.1
Heavy Atom Count: 15
Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CC=CC=C2Cl
InChI: InChI=1S/C13H9ClO/c14-12-9-5-4-8-11(12)13(15)10-6-2-1-3-7-10/h1-9H
InChIKey: VMHYWKBKHMYRNF-UHFFFAOYSA-N
EINECS: 225-936-9
Product Categories: Aromatic Benzophenones & Derivatives (substituted); Functional Materials; Photopolymerization Initiators; C13 to C14; Carbonyl Compounds; Ketones
2-Chlorobenzophenone (CAS NO.5162-03-8) can be used as pharmaceutical intermediates.
mouse | LD | oral | > 500mg/kg (500mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS | National Technical Information Service. Vol. OTS0544006, |
Hazard Codes: Xi, Xn
Risk Statements: 36/37/38-20/21/22
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 37/39-26-24/25-36
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: PC4945633
Hazard Note: Irritant
2-Chlorobenzophenone (CAS NO.5162-03-8) is also named as (2-Chlorophenyl)phenylmethanone ; 2-Chlorobenyl phenyl ketone ; AI3-22112 ; NSC 62529 ; o-Chlorobenzophenone ; Benzophenone, 2-chloro- (6CI,7CI,8CI) ; Methanone, (2-chlorophenyl)phenyl- . 2-Chlorobenzophenone (CAS NO.5162-03-8) is white to yellow crystalline powder.
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