937-20-2

Basic information

• Product Name: 2,4'-Dichloroacetophenone
• Synonyms: Ethanone,2-chloro-1-(4-chlorophenyl)-;2,4'-Dichloroacetophenone 2-Chloro-1-(4-Chlorophenyl)ethanone;2-Chloro-1-(4-chlorophenyl)-1-ethanone;alpha,4-Dichloroacetophenone,97%;à,4-dichloroacetophenone;2,4DICHLOROACETOPHENONE(2,4'-DICHLOROISOMER);2,4'-Dichloroacetophenone;2,4'-Dichloroacetophenone, 98+%
• CAS NO: 937-20-2
• Molecular Formula: C₈H₆Cl₂O
• Molecular Weight: 189.04
• EINECS: 213-323-9
• Product Categories: Benzene series;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 937-20-2.mol
• Article Data: 61

Chemical Properties

• Melting Point: 100-102 °C(lit.)
• Boiling Point: 270 °C(lit.)
• Flash Point: 270°C
• Appearance: white to off-white crystalline powder
• Density: 1.2979 (rough estimate)
• Refractive Index: 1.5640 (estimate)
• BRN: 637861
• CAS DataBase Reference: 2,4'-Dichloroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4'-Dichloroacetophenone(937-20-2)
• EPA Substance Registry System: 2,4'-Dichloroacetophenone(937-20-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 937-20-2(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

Uses

2,4′-Dichloroacetophenone (4-chlorophenacyl chloride) may be used in the synthesis of chiral chlorohydrin by asymmetric reduction., It may be used as an alkylating agent in the Williamson reaction of 7-hydroxycoumarins to form substituted oxoethers.

General Description

2,4′-Dichloroacetophenone is a substituted α-chloro aromatic ketone.2 Its 35/37Cl WURST-QCPMG NMR spectra has been investigated.

Synthetic route

para-chloroacetophenone (99-91-2) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With 1,3-dichloro-5,5-dimethylhydantoin; silica gel In methanol for 1h; Reflux;	98%
With N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; 1,2-dichloro-ethane for 6h; Heating;	97%
With tetrachlorosilane; urea hydrogen peroxide adduct In dichloromethane at 0℃; for 1h;	93%

2,2,2-trichloro-1-(4-chloro-phenyl)-ethanol (5333-82-4) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With [2,2]bipyridinyl; copper(l) chloride In 1,2-dichloro-ethane for 3h; Heating;	93%

N-methyl-N-nitrosotoluene-p-sulfonamide (80-11-5) + 4-chloro-benzoyl chloride (122-01-0) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃; Arndt-Eistert Homologation;	93%

1-chloro-4-(chloroethynyl)benzene (33491-02-0) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With water In 1,2-dichloro-ethane at 20℃; for 14h;	93%
With water; silver fluoride; trifluoroacetic acid at 40℃; for 6h; Green chemistry;	88%
With tetrafluoroboric acid; water In 2,2,2-trifluoroethanol at 80℃; for 10h;	87%
With indium(III) triflate; water In acetic acid at 100℃; Sealed tube;	79%

4-vinylbenzyl chloride (1073-67-2) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With magnesium(II) chloride hexahydrate; oxygen; lithium perchlorate; manganese(ll) chloride In dichloromethane; acetone at 40℃; for 40h; Electrochemical reaction;	93%
With magnesium(II) chloride hexahydrate; cobalt(II) chloride hexahydrate; oxygen; lithium perchlorate In dichloromethane; acetone at 40℃; for 12h; Electrolysis; Sealed tube; chemoselective reaction;	77%
With tris(2,2'-bipyridyl)ruthenium dichloride; chloroform; [bis(acetoxy)iodo]benzene In chloroform at 20℃; for 12h; Irradiation;	77%
With iron(III) chloride; potassium chloride; oxygen; toluene-4-sulfonic acid In tert-butyl methyl ether at 20℃; Irradiation; Green chemistry;	49%

1-(4-chlorophenyl)-2-(dimethyl(oxo)-λ6-sulfanylidene)ethan-1-one (676486-15-0) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane at 20 - 70℃; for 16h;	92%
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane at 20 - 70℃;	78%

1-(p-chlorophenyl)ethyl alcohol (3391-10-4) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With methanol; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at 20℃; for 2h; Reagent/catalyst;	87%
With N,N-dichloro-p-toluenesulfonamide In acetonitrile at 55℃; for 3.5h;	79%
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-formamide at 25℃; for 6h;	84 % Chromat.

1-(4-bromophenyl)ethanol (5391-88-8) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With methanol; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at 20℃; for 2h; Reagent/catalyst;	87%

chloroacetyl chloride (79-04-9) + chlorobenzene (108-90-7) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
aluminium trichloride In carbon disulfide for 2h; Heating;	84%
With carbon disulfide; aluminium trichloride
With aluminium trichloride In carbon disulfide

4-chlorobenzoylmethyl bromide (536-38-9) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With S4N4*SbCl5 In toluene for 3.5h; Heating;	81%
With sodium chloride In acetonitrile
With N-benzyl-N,N,N-triethylammonium chloride; benzenesulfonyl chloride In water at 20℃; for 1.3h; Solvent; Green chemistry;

4-n-chlorophenylacetylene (873-73-4) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
Stage #1: 4-n-chlorophenylacetylene With methanol; gold(III) chloride; silver(I) triflimide In 1,4-dioxane at 45℃; Stage #2: With N-chloro-succinimide In 1,4-dioxane regioselective reaction;	75%
With hydrogenchloride; iodine In dimethyl sulfoxide at 20℃; for 16h;	69%

1-(4-chlorophenyl)-2-diazoethanone (3282-33-5) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With iron(III) chloride; silica gel In dichloromethane at 20℃; for 0.166667h;	75%

1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonyl chloride (55591-23-6) + ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane (58518-76-6) → p-chlorophenacyl chloride (937-20-2) + 1-(4'-chlorophenyl)-3,4,4,5,5,6,6,7,7,8,8,8-dodecafluorooct-2-en-1-one

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride In benzene at 120℃; for 7h;	A 24% B 56%

2-chloro-1,3-bis(4′-chlorophenyl)-1,3-propanedione → 1,3-bis(4-chlorophenyl)propane-1,3-dione (18362-49-7) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
Stage #1: 2-chloro-1,3-bis(4′-chlorophenyl)-1,3-propanedione With [Cu(tris(2-pyridylmethyl)amine)(CH3CN)](ClO4)2; lithium hexamethyldisilazane In diethyl ether; acetonitrile for 48h; Inert atmosphere; Glovebox; Stage #2: With water In diethyl ether; acetonitrile	A n/a B 56%

trifluoromethane sulfonyl chloride (421-83-0) + ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane (58518-76-6) → 1-(4-chlorophenyl)-3,3,3-trifluoro-propan-1-one (121194-36-3) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride In benzene at 120℃; for 7h;	A 51% B 15%

Trichloromethanesulfonyl chloride (2547-61-7) + ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane (58518-76-6) → 3,3-dichloro-1-(4-chlorophenyl)prop-2-en-1-one (41501-65-9) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With ruthenium(II) In benzene at 120℃; for 7h; sealed;	A 41% B 49%

para-chloroacetophenone (99-91-2) → 2,2-dichloro-1-(4-chlorophenyl)ethanone (5157-57-3) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With chloro-trimethyl-silane; potassium nitrate In dichloromethane at 60℃; for 16h;	A n/a B 42%
With aluminum (III) chloride; oxygen; vanadium(V) oxytriisopropoxide; tetra-(n-butyl)ammonium iodide In acetonitrile at 80℃; for 25h;	A 13 %Spectr. B 66 %Spectr.

diphenyl(p-chlorophenylethynyl)selenonium triflate → diphenylselenide (1132-39-4) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With tetrabutyl-ammonium chloride In dichloromethane for 72h; Ambient temperature;	A 36% B 21%

1-(p-chlorophenyl)ethyl alcohol (3391-10-4) + Mangantriacetat → 1-(4-chlorophenyl)ethyl acetate (103966-61-6, 137408-28-7, 137491-94-2, 19759-43-4) + para-chloroacetophenone (99-91-2) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With *5H2O; lithium chloride In acetic acid for 0.3h; Heating;	A 11% B 18% C 2%

1-(p-chlorophenyl)ethyl alcohol (3391-10-4) → 1-(4-chlorophenyl)ethyl acetate (103966-61-6, 137408-28-7, 137491-94-2, 19759-43-4) + para-chloroacetophenone (99-91-2) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With *5H2O; lithium chloride In acetic acid for 0.3h; Heating;	A 11% B 18% C 2%

4-chloro-benzoyl chloride (122-01-0) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With diazomethane; benzene Einleiten von HCl in die Reaktionsloesung unter Kuehlung;

2,2,2-trichloro-1-(4-chloro-phenyl)-ethanol (5333-82-4) → 2-chloro-2-(4-chlorophenyl)acetaldehyde (58369-61-2) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With n-butyllithium

4-vinylbenzyl chloride (1073-67-2) → Z-1-chloro-4-(2-chloroethenyl)benzene (18684-82-7) + (E)-1-(2-chlorovinyl)-4-chlorobenzene (18684-97-4) + 4-chlorobenzaldehyde (104-88-1) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With chlorine dioxide In tetrachloromethane at 52 - 54℃; for 1.66667h; Further byproducts given. Title compound not separated from byproducts;	A 3.2 % Chromat. B 17.6 % Chromat. C 1.0 % Chromat. D 37.5 % Chromat.
With chlorine dioxide In tetrachloromethane at 52 - 54℃; for 1.66667h; Further byproducts given;	A 3.2 % Chromat. B 17.6 % Chromat. C 1.0 % Chromat. D 37.5 % Chromat.

4-vinylbenzyl chloride (1073-67-2) → 2,2-dichloro-1-(4-chlorophenyl)ethanone (5157-57-3) + Z-1-chloro-4-(2-chloroethenyl)benzene (18684-82-7) + (E)-1-(2-chlorovinyl)-4-chlorobenzene (18684-97-4) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With chlorine dioxide In tetrachloromethane at 52 - 54℃; for 1.66667h; Further byproducts given;	A 1.7 % Chromat. B 3.2 % Chromat. C 17.6 % Chromat. D 37.5 % Chromat.

4-vinylbenzyl chloride (1073-67-2) → 2,2-dichloro-1-(4-chlorophenyl)ethanone (5157-57-3) + (E)-1-(2-chlorovinyl)-4-chlorobenzene (18684-97-4) + p-chlorophenacyl chloride (937-20-2) + para-chlorobenzoic acid (74-11-3)

Conditions	Yield
With chlorine dioxide In tetrachloromethane at 52 - 54℃; for 1.66667h; Further byproducts given;	A 1.7 % Chromat. B 17.6 % Chromat. C 37.5 % Chromat. D 6.4 % Chromat.

4-n-chlorophenylacetylene (873-73-4) + acetic acid (64-19-7) → 1-chloro-4-(chloroethynyl)benzene (33491-02-0) + 2,2-dichloro-1-(4-chlorophenyl)ethanone (5157-57-3) + 4-chlorophenacyl acetate (39561-82-5) + para-chloroacetophenone (99-91-2) + 1-Chloro-4-((E)-1,2-dichloro-vinyl)-benzene (84553-28-6) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With perchloric acid at 40℃; Rate constant; Product distribution; Mechanism;	A 4 % Chromat. B 23 % Chromat. C 5 % Chromat. D 10 % Chromat. E 21 % Chromat. F 29 % Chromat.

4-n-chlorophenylacetylene (873-73-4) + acetic acid (64-19-7) → 1-chloro-4-(chloroethynyl)benzene (33491-02-0) + 2,2-dichloro-1-(4-chlorophenyl)ethanone (5157-57-3) + para-chloroacetophenone (99-91-2) + 1-Chloro-4-((E)-1,2-dichloro-vinyl)-benzene (84553-28-6) + 2-chloro-1-(4-chlorophenyl)butane-1,3-dione (84553-23-1) + p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
With perchloric acid at 0 - 40℃; Kinetics; Mechanism;

Methyl 4-chlorobenzoate (1126-46-1) + (C14H29)3MnMgCl → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: t-BuOK / tetrahydrofuran / 2 h / Heating 1.2: 53 percent / tetrahydrofuran / 48 h / 20 °C 2.1: 92 percent / HCl / tetrahydrofuran; dioxane / 16 h / 20 - 70 °C View Scheme

1-(4-chlorophenyl)-2-trimethylsilylacetylene (78704-49-1) → p-chlorophenacyl chloride (937-20-2)

Conditions	Yield
Multi-step reaction with 2 steps 2: 21 percent / n-Bu4NCl / CH2Cl2 / 72 h / Ambient temperature View Scheme

p-chlorophenacyl chloride (937-20-2) → (S)-2-chloro-1-(4-chlorophenyl)ethan-1-ol (178460-78-1)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; f-amphox; hydrogen; potassium carbonate In ethanol; hexane at 25 - 30℃; under 38002.6 Torr; for 4h; Inert atmosphere; Glovebox; Autoclave; enantioselective reaction;	99%
With D-glucose; D-glucose dehydrogenase; NADPH; potassium phosphate buffer; recombinant ketoreductase In water at 20℃; pH=7.0;	97%
With glucose dehydrogenase; pET28-bmgdh-dhcr; sodium carbonate In aq. phosphate buffer; toluene at 30℃; for 24h; pH=6.5; Green chemistry; Enzymatic reaction; enantioselective reaction;	89%

p-chlorophenacyl chloride (937-20-2) → (R)-2-chloro-1-(4-chlorophenyl)ethan-1-ol

Conditions	Yield
With hydrogen; Ru(OTf)[(S,S)-TsDPEN](η6-mesitylene) In methanol at 30℃; under 7600 Torr; for 15h;	99%
With formic acid; C25H29N2O3RuS; potassium formate In water; ethyl acetate at 60℃; for 4h; Inert atmosphere; enantioselective reaction;	94%
With dimethylsulfide borane complex; (1R,2S,3R,5R)-2-(1',3',2'-dioxaborolan-2'-yloxy)apopinan-3-amine In tetrahydrofuran at 20℃; for 1h; enantioselective reaction;	92%

concentrated ammonium chloride + 1-chloro-2-(chloromethyl)benzene (611-19-8) + p-chlorophenacyl chloride (937-20-2) → 1-chloro-2-(4-chlorophenyl)-3-(2-chlorophenyl)propan-2-ol (133001-02-2)

Conditions	Yield
With magnesium In toluene	99%

p-chlorophenacyl chloride (937-20-2) + C9H17N3S → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-cyclooctylidenehydrazine (1569467-56-6)

Conditions	Yield
In ethanol at 20℃;	99%

potassium cyanide + p-chlorophenacyl chloride (937-20-2) → p-chlorobenzoylacetonitrile (4640-66-8)

Conditions	Yield
In ethanol; water at 20℃; for 4h;	99%

p-chlorophenacyl chloride (937-20-2) + 2-nitro-benzaldehyde (552-89-6) → trans-(4-chlorophenyl)(2-(2-nitrophenyl)oxiran-3-yl)methanone

Conditions	Yield
With methanol; sodium at 20℃; for 0.25h; Darzens Condensation;	99%

p-chlorophenacyl chloride (937-20-2) + 5-methyl-2-thiouracil (636-26-0) → 2-(4-chlorobenzoylmethylthio)-5-methylpyrimidin-4(1H)-one sodium salt (119760-69-9)

Conditions	Yield
With sodium hydroxide In ethanol for 0.333333h; Heating;	98%

1,2,4-Triazole (288-88-0) + p-chlorophenacyl chloride (937-20-2) → 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (58905-19-4)

Conditions	Yield
Stage #1: 1,2,4-Triazole With sodium carbonate In toluene at 20℃; for 0.5h; Stage #2: p-chlorophenacyl chloride In toluene Solvent; Reflux;	98%
Stage #1: 1,2,4-Triazole With sodium carbonate In toluene at 20℃; for 0.5h; Stage #2: p-chlorophenacyl chloride In toluene Solvent; Reflux;	98%
With potassium carbonate In acetonitrile at 85℃; for 0.833333h; microwave irradiation;	90%

chlorobenzene (108-90-7) + p-chlorophenacyl chloride (937-20-2) → 1,2-bis(4-chlorophenyl)ethanone (51490-05-2)

Conditions	Yield
Stage #1: chlorobenzene; p-chlorophenacyl chloride With aluminum (III) chloride at 20 - 50℃; for 14.25h; Friedel-Crafts Acylation; Cooling with ice; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water	98%
With aluminum (III) chloride In dichloromethane at 20℃;	89%

p-chlorophenacyl chloride (937-20-2) + Acetone thiosemicarbazone (1752-30-3) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(propan-2-ylidene)hydrazine (163107-37-7)

Conditions	Yield
In ethanol at 20℃;	98%
In ethanol at 20 - 50℃;

C7H13N3S + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(hex-5-en-2-ylidene)hydrazine (1569467-26-0)

Conditions	Yield
In ethanol at 20℃;	98%

furan-2-aldehyde thiosemicarbazone (5419-96-5) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(furan-2-ylmethylene)hydrazine (307325-12-8)

Conditions	Yield
In ethanol at 20℃;	98%

p-chlorophenacyl chloride (937-20-2) + 2-((1H-indol-3-yl)methylene)hydrazine-1-carbothioamide (6868-28-6) → 1-((1H-indol-3-yl)methylene)-2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazine (307544-76-9)

Conditions	Yield
In ethanol at 20℃;	98%

2-[1-(2-naphthenyl)ethyledene]hydrazinecarbothioamide (133477-39-1) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(1-(naphthalen-2-yl)ethylidene)hydrazine (36941-40-9)

Conditions	Yield
In ethanol at 20℃;	98%

2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)hydrazine-1-carbothioamide (52831-78-4) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(1-(2H-chromen-2-oxo-3-yl)ethylidene)hydrazine (1359132-64-1)

Conditions	Yield
In ethanol at 20℃;	98%

5-chloro-2-nitrobenzaldehyde (6628-86-0) + p-chlorophenacyl chloride (937-20-2) → trans-(2-(5-chloro-2-nitrophenyl)oxiran-3-yl)(4-chlorophenyl)methanone

Conditions	Yield
With methanol; sodium at 20℃; for 0.25h; Darzens Condensation;	98%

4-phenyl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (16629-40-6) + p-chlorophenacyl chloride (937-20-2) → 1-(4-chlorophenyl)-2-[(4-phenyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl)thio]ethanone (325693-94-5)

Conditions	Yield
With potassium carbonate In acetone for 3h; Heating / reflux;	97%

2-octanone thiosemicarbazone (1752-38-1) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(octan-2-ylidene)hydrazine (384808-58-6)

Conditions	Yield
In ethanol at 20℃;	97%

C9H15N3S (1448514-14-4) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(4,4-dimethylcyclohex-2-enylidene)hydrazine (1569467-49-7)

Conditions	Yield
In ethanol at 20℃;	97%

C9H17N3S (387847-19-0) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(1-cyclohexylethylidene)hydrazine (1569467-62-4)

Conditions	Yield
In ethanol at 20℃;	97%

thiophene-2-carbaldehyde thiosemicarbazone (5351-91-7) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(thiophen-2-ylmethylene)hydrazine (464224-97-3)

Conditions	Yield
In ethanol at 20℃;	97%

acetophenonethiosemicarbazone (2302-93-4) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(1-phenylethylidene)hydrazine (36937-52-7)

Conditions	Yield
In ethanol at 20℃;	97%

1-(naphthalen-1-ylmethylene)thiosemicarbazide (5351-81-5) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(naphthalen-1-ylmethylene)hydrazine (464224-98-4)

Conditions	Yield
In ethanol at 20℃;	97%

1,2-diamino-benzene (95-54-5) + p-chlorophenacyl chloride (937-20-2) → 2-(4-chlorophenyl)quinoxaline (17286-63-4)

Conditions	Yield
With sodium hydrogencarbonate In dimethyl sulfoxide at 120℃; for 24h;	97%
With Saccharomyces cerevisiae In acetonitrile at 25℃; for 18h; Green chemistry;	82%

2,4-dinitrobenzaldehyde (528-75-6) + p-chlorophenacyl chloride (937-20-2) → C15H9ClN2O6

Conditions	Yield
With sodium methylate In methanol at 15℃; for 0.25h; Darzens Condensation;	97%

2-(phenylamino)pyridine (6631-37-4) + p-chlorophenacyl chloride (937-20-2) → 2-(4-chlorophenyl)-1-(pyridin-2-yl)-1H-indole

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium fluoride In methanol at 90℃; for 24h;	97%

2,3-dihydro-1H-1,2,4-triazole-3-thione (3179-31-5) + p-chlorophenacyl chloride (937-20-2) → 1-(4-Chloro-phenyl)-2-(1H-[1,2,4]triazol-3-ylsulfanyl)-ethanone; hydrochloride

Conditions	Yield
In isopropyl alcohol for 0.0833333h; Heating;	96%

ammonium thiocyanate + p-chlorophenacyl chloride (937-20-2) → 1-(4-chloro-phenyl)-2-thiocyanato-ethanone (19339-59-4)

Conditions	Yield
In water; isopropyl alcohol at 20℃; for 27h;	96%

pyridine-3-carbaldehyde thiosemicarbazone (555-90-8) + p-chlorophenacyl chloride (937-20-2) → 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(pyridin-3-ylmethylene)hydrazine (328127-98-6)

Conditions	Yield
In ethanol at 20℃;	96%

Upstream product

• 1126-46-1 Methyl 4-chlorobenzoate 
• 5391-88-8 1-(4-bromophenyl)ethanol 
• 3282-33-5 1-(4-chlorophenyl)-2-diazoethanone 
• 1073-67-2 4-vinylbenzyl chloride 
• 873-73-4 4-n-chlorophenylacetylene 
• 33491-02-0 1-chloro-4-(chloroethynyl)benzene 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 122-01-0 4-chloro-benzoyl chloride 
• 53896-48-3 2-iodo-4'-chloroacetophenone 
• 99-91-2 para-chloroacetophenone 
• 135063-58-0 2-chloro-1-(4-chlorophenyl)ethenyl methyl ether 
• 5333-82-4 2,2,2-trichloro-1-(4-chloro-phenyl)-ethanol 
• 78704-49-1 1-(4-chlorophenyl)-2-trimethylsilylacetylene 
• 676486-15-0 1-(4-chlorophenyl)-2-(dimethyl(oxo)-λ⁶-sulfanylidene)ethan-1-one 

Downstream Products

• 486439-05-8 4-[2-(4-chloro-phenyl)-2-oxo-ethyl]-piperazine-1-carboxylic acid ethyl ester 
• 24840-75-3 4-(4-chlorophenyl)-2-methyl-1,3-thiazole 
• 98849-31-1 1-Chloro-2-(4-chloro-phenyl)-4-[1,3]dioxolan-2-yl-butan-2-ol 
• 76850-04-9 1-[2-(4-Chloro-phenyl)-2-oxo-ethyl]-4-oxy-1H-pyrazin-2-one 
• 161689-52-7 2-amino-6-[2-oxo-2-(4-chlorophenyl)ethylthio]-4-(furan-2-yl)pyridine-3,5-dicarbonitrile 
• 161689-45-8 2-Amino-4-(2-chloro-phenyl)-6-[2-(4-chloro-phenyl)-2-oxo-ethylsulfanyl]-1,4-dihydro-pyridine-3,5-dicarbonitrile 
• 1669-71-2 1-chloro-2-(4-chloro-phenyl)-propan-2-ol 
• 828-46-6 1-Chlor-2-<4-chlor-phenyl>-butan-2-ol 
• 974-44-7 1,3-Dichlor-2,4-bis-(4-chlor-phenyl)-hexan-2,4-diol 
• 23080-23-1 1,5-bis(4-chlorophenyl)-3-thiapentane-1,5-dione 
• 873993-03-4 1-chloro-4-(1,1,2-trichloro-ethyl)-benzene 
• 74-11-3 para-chlorobenzoic acid 
• 75822-38-7 1-(4-chlorophenacyl)isatin 
• 376381-85-0 7-[2-(4-chlorophenyl)-2-oxoethoxy]-4-(4-methoxyphenyl)-2H-2-chromenone 

Relevant articles and documents

Tris-(2-pyridylmethyl)amine-ligated Cu(II) 1,3-diketonate complexes: Anaerobic retro-Claisen and dehalogenation reactivity of 2-chloro-1,3-diketonate derivatives

We report synthetic, structural and reactivity investigations of tris-(2-pyridylmethyl)amine (TPA)-ligated Cu(ii) 1,3-diketonate complexes. These complexes exhibit anaerobic retro-Claisen type C-C bond cleavage reactivity which exceeds that found in analo

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.

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.