90-98-2

Usage

Uses

Used in Pharmaceutical Industry:
4,4'-Dichlorobenzophenone is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical structure allows it to be a key component in the development of new pharmaceutical compounds, enhancing their therapeutic properties and effectiveness.
Used in Organic Synthesis:
In the field of organic synthesis, 4,4'-Dichlorobenzophenone is utilized as a valuable intermediate. Its reactivity with other chemical groups makes it suitable for the creation of a wide range of organic compounds, contributing to the advancement of chemical research and development.
Used in Agrochemicals:
4,4'-Dichlorobenzophenone plays a significant role in the agrochemical industry as well. It is used as a raw material and intermediate in the synthesis of various agrochemical products, such as pesticides and herbicides, which are essential for maintaining agricultural productivity and crop protection.
Used in Dye Industry:
The dye industry also benefits from the use of 4,4'-Dichlorobenzophenone. It is employed as an intermediate in the production of various dyes, contributing to the development of new colorants and improving the quality of existing dyes.
Used in Polymer Synthesis:
4,4'-Dichlorobenzophenone can be used to synthesize polyether-polyketones, a type of polymer with potential applications in various industries. Its use in polymer synthesis helps to reduce the overall costs of producing these materials, making them more accessible and affordable.
Used in Environmental Applications:
As a metabolic product resulting from the degradation of DDT, 4,4'-Dichlorobenzophenone has environmental implications. Its study can provide insights into the breakdown of harmful pollutants and contribute to the development of strategies for environmental remediation and pollution control.

Preparation

4,4'-Dichlorobenzophenone is prepared by the acylation of chlorobenzene with 4-chlorobenzoyl chloride. The conversion is typically conducted in the presence of an aluminium chloride catalyst in a petroleum ether solvent.ClC6H5C(O)Cl + C6H5Cl → (ClC6H4)2CO + HCl

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 1201, 1989 DOI: 10.1021/jo00266a039Tetrahedron Letters, 36, p. 8411, 1995 DOI: 10.1016/0040-4039(95)01802-O

Purification Methods

Recrystallise it from EtOH [Wagner et al. J Am Chem Soc 108 7727 1986]. The semicarbazone has m 192-193o (from H2O). [Beilstein 7 H 420, 7 I 228, 7 II 359, 7 III 2076, 7 IV 1376.]

Synthetic route

Dicofol (115-32-2) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With potassium hydroxide In water at 0℃; for 72h;	100%
for 6h; Irradiation;	95 mg
for 6h; Product distribution; Mechanism; Irradiation;	95 mg

4,4'-dichlorobenzophenone (90-97-1) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With 4-Benzoylpyridine In acetone at 20℃; for 32h; UV-irradiation; Inert atmosphere;	99%
With chromium(VI) oxide In neat (no solvent) at 20℃; for 0.00833333h;	98%
With picoline; tert.-butylhydroperoxide; chlorophyllin coppered trisodium salt In water; acetone at 80℃; for 10h; chemoselective reaction;	98%

chloroformic acid ethyl ester (541-41-3) + (4-chlorophenyl)zinc(II) bromide (150766-93-1) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
at 20℃; for 4.5h;	99%

4,4'-dichlorodiphenylmethane (101-76-8) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With oxygen; sodium t-butanolate In dimethyl sulfoxide at 50℃; for 5h; Sealed tube;	98%
With 18-crown-6 ether; potassium tert-butylate; oxygen In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;	88%
With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; for 32h;	68%

1,1-bis(4-chlorophenyl)-2,2-dichloroethylene (72-55-9) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With chromium(VI) oxide In acetic acid for 4h; Heating;	98%
With chromium(VI) oxide; acetic acid
With nitric acid at 100℃;

4,4'-dichlorobenzophenone oxime (1714-50-7) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With manganese(IV) oxide In neat (no solvent) at 20℃; for 0.0333333h;	98%
With sodium nitrite In water; acetonitrile at 40℃; for 2h;	96%
With diphenyl ditelluride; oxygen In ethyl acetate for 24h; Irradiation;	96%

4-Chlorophenylboronic acid (1679-18-1) + 4-chloro-benzoyl chloride (122-01-0) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With [Ph2P(ferrocene-1,1′-diyl)ONHCH2CH2NHC(NH2)NH2]Cl*0.4chloroform; palladium diacetate; sodium carbonate In water; toluene at 50℃; for 1h; Schlenk technique; Inert atmosphere;	98%
With [Pd(3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide)(PPh3)Cl2]; potassium carbonate In water at 100℃; for 3h; Suzuki-Miyaura Coupling;	84%

bis(4'-chlorophenyl)acetic acid (83-05-6) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With mercury(II) fluoride; oxygen In acetonitrile at 25℃; for 24h; Irradiation;	96%

2,2’-bis(4-(chloro)phenyl)acetonitrile (20968-04-1) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With oxygen; potassium carbonate In water; dimethyl sulfoxide Ambient temperature;	95%

4-Chlorophenylboronic acid (1679-18-1) + C11H9ClN2 → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium acetate; copper(II) trifluoroacetate In cyclohexane at 130℃; for 24h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere;	95%

1,1-bis(p-chlorophenyl)ethene (2642-81-1) + dimedone (126-81-8) → 4,4'-Dichlorobenzophenone (90-98-2) + 2,2-bis(4-chlorophenyl)-6,6-dimethyl-2,3,4,5,6,7-hexahydrobenzo[b]furan-4-one

Conditions	Yield
With manganese triacetate In acetic acid for 0.05h; Heating;	A 4% B 94%

tris(4-chlorophenyl)bismuthane (5575-51-9) + 4-chloro-benzoyl chloride (122-01-0) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With tributyl-amine In 1-methyl-pyrrolidin-2-one at 80℃; for 3h; Schlenk technique; Inert atmosphere;	94%

4-chloro-benzoyl chloride (122-01-0) + chlorobenzene (108-90-7) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
at 270℃;	93.5%
With Perfluorooctanesulfonic acid; ytterbium(III) triflate In various solvent(s) at 120℃; for 24h; Friedel-Crafts acylation;	86%
With hafnium(IV) trifluoromethanesulfonate; trifluorormethanesulfonic acid at 120℃; for 15h;	82%

2,2-bis-(4-chloro-phenyl)-1,3-dithiolane → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With bromine In tetrachloromethane at 30 - 40℃; for 0.666667h;	93%

tetrakis-(4-chloro-phenyl)-ethane-1,2-diol (5418-23-5) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With sodium hypochlorite In acetonitrile at 20℃; for 4h;	92%
beim Schmelzen;
With acetic acid

S-(2-pyridinyl) 4-chlorobenzenecarbothioate (74032-43-2) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0) In N,N-dimethyl-formamide at 50℃; for 3h;	92%

1,1-bis(p-chlorophenyl)ethene (2642-81-1) + ethyl acetoacetate (141-97-9) → ethyl cis-6,6-bis(4-chlorophenyl)-3-hydroxy-3-methyl-1,2-dioxane-4-carboxylate + 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With air; manganese(II) acetate; manganese triacetate In acetic acid at 23℃; for 12h;	A 91% B 9%

1-Chloro-4-iodobenzene (637-87-6) + carbon monoxide (201230-82-2) + tris(4-chlorophenyl)bismuthane (5575-51-9) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 5h; Green chemistry;	91%

1-Chloro-4-iodobenzene (637-87-6) + chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With potassium carbonate In ethanol at 75℃; for 6h;	91%

1-Chloro-4-iodobenzene (637-87-6) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With potassium carbonate In ethylene glycol at 110℃; for 6.8h;	90%
With 4,4'-di-tert-butyl-2,2'-bipyridine; nickel dibromide; zinc In 1,4-dioxane at 120℃; for 6h; Inert atmosphere; Sealed tube;	76%

1,1-bis(p-chlorophenyl)ethene (2642-81-1) + manganese(III) acetylacetonate (14284-89-0) → 1-(p-chlorophenyl)-1,4-pentanedione (53842-12-9) + 4-acetyl-6,6-bis(4-chlorophenyl)-3-methyl-1,2-dioxan-3-ol (133216-65-6) + 2-acetyl-5,5-bis(4-chlorophenyl)-2-methyl-4,5-dihydrofuran (135507-94-7) + 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With air; acetic acid at 23℃; for 12h; Further byproducts given;	A 3% B 88% C 2% D 3%

1,1-bis(p-chlorophenyl)ethene (2642-81-1) + manganese(III) acetylacetonate (14284-89-0) → 4-acetyl-6,6-bis(4-chlorophenyl)-3-methyl-1,2-dioxan-3-ol (133216-65-6) + 2,2-bis(4-chlorophenyl)-2-hydroxyethyl acetate (135507-97-0) + 2-acetyl-5,5-bis(4-chlorophenyl)-2-methyl-4,5-dihydrofuran (135507-94-7) + 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With air; acetic acid at 23℃; for 12h; Further byproducts given;	A 88% B 1% C 2% D 3%

1,1-bis(p-chlorophenyl)ethene (2642-81-1) + acetic acid (64-19-7) → 4-acetyl-6,6-bis(4-chlorophenyl)-3-methyl-1,2-dioxan-3-ol (133216-65-6) + 2,2-bis(4-chlorophenyl)-2-hydroxyethyl acetate (135507-97-0) + 2-acetyl-5,5-bis(4-chlorophenyl)-2-methyl-4,5-dihydrofuran (135507-94-7) + 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With air; manganese(III) acetylacetonate at 23℃; for 12h; Further byproducts given;	A 88% B 1% C 2% D 3%

bis(4-chlorophenyl)(hydroxy)acetic acid (23851-46-9) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With sodium periodate; dibenzo-18-crown-6; N-benzyl-N,N,N-triethylammonium chloride In methanol for 2.1h;	88%

bromochlorobenzene (106-39-8) + 4-chlorobenzaldehyde (104-88-1) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
Stage #1: bromochlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Stage #3: With iodine; potassium carbonate In tert-butyl alcohol for 3h; Reflux;	88%
Stage #1: bromochlorobenzene With magnesium In tetrahydrofuran at 20℃; for 1h; Stage #2: 4-chlorobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 2h; Stage #3: With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; potassium carbonate In tetrahydrofuran; tert-butyl alcohol for 20h; Reflux; Darkness;	65%
With Ni(dmbpy)Br2; sodium carbonate In acetone at 25℃; for 8h; Sealed tube; Inert atmosphere; Irradiation;	57%

1-Chloro-4-iodobenzene (637-87-6) + 4-Chlorophenylboronic acid (1679-18-1) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With potassium carbonate at 95℃; for 2h; Suzuki Coupling; Sealed tube; Inert atmosphere;	88%

carbon monoxide (201230-82-2) + chlorobenzene (108-90-7) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); iodine; silver trifluoromethanesulfonate at 150℃; under 3040.2 Torr; for 22h;	88%

1-Chloro-4-iodobenzene (637-87-6) + dicobalt octacarbonyl → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With air; 2,3-dimethylnaphthalene In acetonitrile for 0.00277778h; microwave irradiation;	87%

1-Chloro-4-iodobenzene (637-87-6) + carbon monoxide (201230-82-2) + 4-Chlorophenylboronic acid (1679-18-1) → 4,4'-Dichlorobenzophenone (90-98-2)

Conditions	Yield
With potassium carbonate In methoxybenzene at 80℃; under 760.051 Torr; for 6h; carbonylative Suzuki-Miyaura cross-coupling;	87%

4,4'-Dichlorobenzophenone (90-98-2) → 4,4'-dichlorobenzophenone (90-97-1)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃;	100%
With sodium tetrahydroborate In ethanol at 20℃; for 0.5h; Inert atmosphere;	100%
With sodium tetrahydroborate In methanol at 0 - 20℃; for 2.25h;	99%

4,4'-Dichlorobenzophenone (90-98-2) → 4,4'-dichlorobenzophenone oxime (1714-50-7)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol Heating;	100%
With hydroxylamine hydrochloride; sodium acetate In ethanol for 24h; Heating;	91%
With hydroxylamine; sodium hydroxide In methanol at 40℃; for 0.166667h;	91.6%

4,4'-Dichlorobenzophenone (90-98-2) + 1-phenylprop-2-en-1-amine hydrochloride → [bis-(4-chloro-phenyl)-methylene]-(1-phenyl-allyl)-amine

Conditions	Yield
With titanium tetrachloride; triethylamine In 1,2-dimethoxyethane at -78 - 20℃;	100%

4,4'-Dichlorobenzophenone (90-98-2) → 4,4'-dichloro-3,3'-dinitrobenzophenone (7498-65-9)

Conditions	Yield
With sulfuric acid; nitric acid In water; 1,2-dichloro-ethane	99%
With sodium nitrate; sulfuric acid In water; 1,2-dichloro-ethane	98%
With sulfuric acid; nitric acid at 100℃;

4,4'-Dichlorobenzophenone (90-98-2) → tetrakis-(4-chloro-phenyl)-ethane-1,2-diol (5418-23-5)

Conditions	Yield
With CdS(x)Se(1-x) x:0-1;; para-thiocresol In hexane for 22h; Inert atmosphere; Irradiation;	99%
With methanol; gallium nitride at 20℃; for 12h; Irradiation; Sealed tube;	97%
With zinc(II) chloride; zinc In tetrahydrofuran; water for 1h; Ambient temperature;	92%

morpholine (110-91-8) + 4,4'-Dichlorobenzophenone (90-98-2) → bis(4-(1-morpholino)phenyl)methanone (115043-23-7)

Conditions	Yield
With sodium hydride; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; tert-butyl alcohol; bis(acetylacetonate)nickel(II) In tetrahydrofuran at 65℃; for 4h; McMurry olefination;	99%
With sodium hydride; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; tert-butyl alcohol; bis(acetylacetonate)nickel(II) In tetrahydrofuran at 65℃;	92%

4,4'-Dichlorobenzophenone (90-98-2) + trimethyl orthoformate (149-73-5) → 4,4’-dichlorobenzophenone dimethyl acetal (6861-53-6)

Conditions	Yield
With triethylamine In methanol at 20℃; for 48h;	99%
With bismuth(lll) trifluoromethanesulfonate In methanol for 24h; Heating;	95%
With perchloric acid In methanol for 7.5h; Reflux;	88.74%
With Montmorillonite K 10; toluene-4-sulfonic acid In methanol at 20℃; for 72h;	86%
perchloric acid In methanol at 25 - 30℃; for 7.5h; Reflux;

1,1,1-trichloroethane (71-55-6) + 4,4'-Dichlorobenzophenone (90-98-2) → 4,4'-dichloro-3,3'-dinitrobenzophenone (7498-65-9)

Conditions	Yield
With sulfuric acid; nitric acid	99%

triethylsilane (617-86-7) + 4,4'-Dichlorobenzophenone (90-98-2) → (bis(4-chlorophenyl)methoxy)triethylsilane (1334477-75-6)

Conditions	Yield
With C16H25AlBN6(1+)*C19H3BF15(1-) In chloroform-d1 at 100℃; for 4h;	99%
Stage #1: 4,4'-Dichlorobenzophenone With C8H10BiCl2N; C4H6AgN2(1+)*C24H12BCl8(1-) In dichloromethane-d2 at 25℃; Stage #2: triethylsilane In dichloromethane at 25℃;	99%

hex-1-yne (693-02-7) + 4,4'-Dichlorobenzophenone (90-98-2) → 1,1'-bis(4-chlorophenyl)hept-2-yn-1-ol

Conditions	Yield
Stage #1: hex-1-yne With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 4,4'-Dichlorobenzophenone In tetrahydrofuran at -78 - 20℃;	99%

methylmagnesium bromide (75-16-1) + 4,4'-Dichlorobenzophenone (90-98-2) → chlorfenethol (80-06-8)

Conditions	Yield
In tetrahydrofuran; dibutyl ether for 2h; Schlenk technique; Inert atmosphere;	98%
With diethyl ether; benzene
In diethyl ether for 1h;

4,4'-Dichlorobenzophenone (90-98-2) → 4,4'-benzophenone disodium disulfonate (97586-32-8)

Conditions	Yield
With copper(II) sulfate; sodium sulfite In water at 230℃; for 3h;	98%

orthoformic acid triethyl ester (122-51-0) + 4,4'-Dichlorobenzophenone (90-98-2) → 4,4'-dichlorobenzophenone diethyl acetal (116545-06-3)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In ethanol for 24h; Heating;	98%
With Montmorillonite K 10; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 60℃; for 72h;	10%

allyl bromide (106-95-6) + 4,4'-Dichlorobenzophenone (90-98-2) → 1,1-bis(4-chloro-phenyl)but-3-en-1-ol

Conditions	Yield
Stage #1: allyl bromide; 4,4'-Dichlorobenzophenone With magnesium at 20℃; for 0.1h; Neat (no solvent); Stage #2: With ammonium chloride Saturated solution;	98%
With copper; zinc at 20℃; for 0.25h; Barbier-type reaction;	96%
Stage #1: allyl bromide With iodine; magnesium In diethyl ether at 0℃; for 1h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: 4,4'-Dichlorobenzophenone In diethyl ether at 0℃; for 12h; Schlenk technique; Inert atmosphere; Reflux;	95%
With neodymium; iodine In tetrahydrofuran at 20℃; for 2h; Barbier Coupling Reaction; Inert atmosphere; regioselective reaction;	75%

methanol (67-56-1) + 4,4'-Dichlorobenzophenone (90-98-2) → 4,4’-dichlorobenzophenone dimethyl acetal (6861-53-6)

Conditions	Yield
With trimethyl orthoformate for 24h; Heating;	97%
With trifluorormethanesulfonic acid; trimethyl orthoformate In nitromethane for 4h; Heating;	87%

ethylene glycol (107-21-1) + 4,4'-Dichlorobenzophenone (90-98-2) → 2,2-di(4-chlorophenyl)-1,3-dioxolane (19018-66-7)

Conditions	Yield
With 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt In xylene at 120℃;	97%
With toluene-4-sulfonic acid In toluene for 40h; Heating;	87%

4,4'-Dichlorobenzophenone (90-98-2) + pentyl 3,5-bis(trifluoromethyl)phenyl sulfone (667458-80-2) → C18H18Cl2

Conditions	Yield
With phosphazene base-P4-tert-butyl In tetrahydrofuran; hexane at 0 - 20℃; Julia-Kocienski olefination;	97%

trimethyl(difluoromethyl)silane (65864-64-4) + 4,4'-Dichlorobenzophenone (90-98-2) → 1,1-bis-(4-chloro-phenyl)-2,2-difluoro-ethanol (841-31-6)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	97%

potassium cyanide (151-50-8) + 4,4'-Dichlorobenzophenone (90-98-2) → 5,5'-bis-(4-chloro-phenyl)-imidazolidine-2,4-dione (23186-92-7)

Conditions	Yield
With ammonium carbonate In various solvent(s) modified Bucherer-Bergs reaction; Heating;	96%

isoniazid (54-85-3) + 4,4'-Dichlorobenzophenone (90-98-2) → isonicotinic acid [bis-(4-chloro-phenyl)-methylene]-hydrazide

Conditions	Yield
With toluene-4-sulfonic acid at 60 - 70℃; for 0.333333h;	96%

diisopropyl (E)-azodicarboxylate (2446-83-5) + 4,4'-Dichlorobenzophenone (90-98-2) → diisopropyl 2-[bis(4-chlorophenyl)methylene]hydrazine-1,1-dicarboxylate (1041432-63-6)

Conditions	Yield
With triphenylphosphine In toluene at 110℃; for 12h;	96%

Upstream product

• 60-29-7 diethyl ether 
• 15719-64-9 methylammonium carbonate 
• 64-17-5 ethanol 
• 7457-25-2 bis-(4-chlorophenyl)-dichloromethane 
• 101-76-8 4,4'-dichlorodiphenylmethane 
• 1066-30-4 chromium(lll) acetate 
• 50-29-3 p,p'-DDT 
• 72-55-9 1,1-bis(4-chlorophenyl)-2,2-dichloroethylene 
• 3547-04-4 1,1-bis(4-chlorophenyl)ethane 
• 3988-03-2 bis(4-bromophenyl)methanone 
• 5418-23-5 tetrakis-(4-chloro-phenyl)-ethane-1,2-diol 
• 64-19-7 acetic acid 
• 98-56-6 4-chlorobenzotrifluoride 
• 108-90-7 chlorobenzene 

Downstream Products

• 101875-96-1 bis(4-chlorophenyl)(pyridin-2-yl)methanol 
• 5418-23-5 tetrakis-(4-chloro-phenyl)-ethane-1,2-diol 
• 15999-71-0 6,6-bis(4-chlorophenyl)fulvene 
• 14212-38-5 bis(4-chlorophenyl)methanamine 
• 408537-45-1 ethyl 3,3-bis(4-chlorophenyl)-3-hydroxypropanoate 
• 3010-80-8 tris(p-chlorophenyl)methanol 
• 90-94-8 bis(p-dimethylaminophenyl)methanone 
• 14442-40-1 ethyl 3,3-bis(4-chlorophenyl)-2-cyanoacrylate 
• 2675-34-5 4,4'-dichloro-benzophenone-(2,4-dinitro-phenylhydrazone) 
• 2642-81-1 1,1-bis(p-chlorophenyl)ethene 
• 80-06-8 chlorfenethol 
• 912-17-4 1,2-diphenyl-1,2-bis-(4-chlorophenyl)-ethanediol 
• 219795-10-5 9-(bis(4-chlorophenyl)methylene)-9H-fluorene 
• 14984-21-5 4,4'-bis(phenoxy)benzophenone 

Relevant academic research and scientific papers

Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes

An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.

Nitrosoarene-Catalyzed HFIP-Assisted Transformation of Arylmethyl Halides to Aromatic Carbonyls under Aerobic Conditions

A rare metal-free nucleophilic nitrosoarene catalysis accompanied by highly hydrogen-bond-donor (HBD) solvent, 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), organocatalytically converts arylmethyl halides to aromatic carbonyls. This protocol offers an effective means to access a diverse array of aromatic carbonyls with good chemoselectivity under mild reaction conditions. The activation of arylmethyl halides by HFIP to generate stable carbocation and autoxidation of in situ generated hydroxylamine to nitrosoarene in the presence of atmospheric O2 are the keys to success.

Palladium imine-pyridine-imine complex immobilized on graphene oxide as a recyclable catalyst for the carbonylative homo-coupling of aryl halides

A heterogeneous 3-N,N,N-(II) Pd(OAc)2 catalyst was prepared from the reaction of Pd(OAc)2 with Si-Prn-N = C-Py-C = N-Prn-Si immobilized on graphene oxide (GO-Si-Prn-N = C-Py-C = N-Prn-Si-GO). The prepared catalyst was characterized by inductively coupled plasma optical emission spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, Raman spectroscopy, energy dispersive X-ray spectroscopy, X-ray diffraction, UV-vis spectroscopy, BET surface area, scanning electron microscopy, transmission electron microscopy, and thermogravimetric analysis. The catalyst was employed as a heterogeneous catalyst for carbonylative homo-coupling of aryl iodides and bromides under carbon monoxide gas-free condition. Cr(CO)6 was used as the carbon monoxide source and the desired symmetrical diaryl ketones were achieved in good to excellent yields. Moreover, the catalyst was reused up to five consecutive cycles without significant loss of activity.

Palladium nanoparticles on amino-modified silica-catalyzed C–C bond formation with carbonyl insertion

Abstract: A practical and heterogeneously catalyzed Stille, homo-coupling, and Suzuki carbonylation reaction has been reported using Pd nanoparticles supported on amino-vinyl silica-functionalized magnetic carbon nanotube (CNT@Fe3O4@SiO2-Pd) for the efficient synthesis of symmetrical and unsymmetrical diaryl ketones from aryl iodides. A wide variety of symmetrical and unsymmetrical diaryl ketones were obtained in high yields under CO gas-free conditions using Mo(CO)6 as an efficient carbonyl source. Considering the atom economy of Ph3SnCl, less than an equimolar amount can be applied in Stille transformation, which is of great importance due to the toxicity of organotin derivatives. Moreover, no phosphine ligand and external reducing agent were necessary in these coupling carbonylation reactions. This heterogeneous Pd catalyst offers high activity with very low palladium leaching. Finally, the catalyst can be reused and recycled for six steps without loss in activity, exhibiting good example of sustainable methodology. Graphic abstract: [Figure not available: see fulltext.].

Preparation method 4,4 ' -difluorobenzophenone and intermediate thereof

The invention discloses 4-4' -difluorobenzophenone and a preparation method of an intermediate thereof. The preparation method of 4, 4 '- difluorobenzophenone comprises the following steps: S1: 4 - chlorobenzyl chloride and chlorobenzene react under first catalyst to obtain 4, 4' -dichlorophenylmethane. The first catalyst is Lewis acid and/or a molecular sieve with Lewis acid center. S2: The 4, 4 '-dichlorophenylmethane and oxidant are subjected to an oxidation reaction under the action second catalyst to obtain 4, 4' -dichlorobenzophenone. S3: The 4, 4' -dichlorobenzophenone and the alkali metal fluoride are subjected to a halogenation reaction to obtain the invention. The 4' - difluorobenzophenone and the intermediate thereof disclosed by the invention are high in selectivity, high in yield, low in raw material cost, mild in process condition, high in safety and wide in industrial prospect.

Organotellurium-catalyzed oxidative deoximation reactions using visible-light as the precise driving energy

Irradiated by visible light, the recyclable (PhTe)2-catalyzed oxidative deoximation reaction could occur under mild conditions. In comparison with the thermo reaction, the method employed reduced catalyst loading (1 mol% vs. 2.5 mol%), but afforded elevated product yields with expanded substrate scope. This work demonstrated that for the organotellurium-catalyzed reactions, visible light might be an even more precise driving energy than heating because it could break the Te–Te bond accurately to generate the active free radical catalytic intermediates without damaging the fragile substituents (e.g., heterocycles) of substrates. The use of O2 instead of explosive H2O2 as oxidant affords safer reaction conditions from the large-scale application viewpoint.

PhSe(O)OH/NHPI-catalyzed oxidative deoximation reaction using air as oxidant

A novel oxidative deoximation method was developed in this article. Compared with the reported organoselenium-catalyzed oxidative deoximation reaction, this reaction employed N-hydroxyphthalimide (NHPI) as the co-catalyst, so that the oxidative deoximation reaction could utilize air as oxidant in the green DMC solvent under mild reaction conditions. Control experiments and X-ray photoelectron spectroscopy (XPS) analysis results indicated that NHPI was essential for activating the catalytic organoselenium species. It could accelerate the activation of molecular oxygen in air to promote the reaction process. The reaction can avoid metal residues in product and is of potential application values in pharmaceutical industry due to the transition metal-free process.

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.

Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis

A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.

Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions

A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.