56041-57-7

Basic information

• Product Name: 2,3-Dichloroacetophenone
• Synonyms: 1-(2,3-DICHLOROPHENYL)ETHAN-1-ONE;2',3'-Dichloroacetophenone;2,3-Dichloroacetophenone;1-(2,3-Dichlorophenyl)ethanone;Ethanone,1-(2,3-dichlorophenyl)-
• CAS NO: 56041-57-7
• Molecular Formula: C₈H₆Cl₂O
• Molecular Weight: 189.04
• EINECS: 259-954-3
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 56041-57-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 106℃
• Boiling Point: 67 °C
• Flash Point: 106-108°C/2mm
• Appearance: colorless to pale yellow liquid
• Density: 1.293
• Vapor Pressure: 0.0258mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• BRN: 2438815
• CAS DataBase Reference: 2,3-Dichloroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dichloroacetophenone(56041-57-7)
• EPA Substance Registry System: 2,3-Dichloroacetophenone(56041-57-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-22
• Safety Statements: 26-36/37/39-37/39-36
• Hazardous Substances Data: 56041-57-7(Hazardous Substances Data)

Usage

Chemical Properties

colorless to pale yellow liquid

InChI:InChI=1/C8H6Cl2O/c1-5(11)6-3-2-4-7(9)8(6)10/h2-4H,1H3

Synthetic route

1,2-dichloro-benzene (95-50-1) → 2',3'-dichloroacetophenone (56041-57-7)

Conditions	Yield
With n-butyllithium; acetic anhydride In tetrahydrofuran; hexane	75%
With n-butyllithium; acetic anhydride In tetrahydrofuran; hexane	75%

2,3-Dichloro-α-methylbenzyl alcohol (54798-91-3) + sodium hydrogensulfite → 2',3'-dichloroacetophenone (56041-57-7)

Conditions	Yield
With sodium hypochlorite In acetic acid	65%
With sodium hypochlorite In acetic acid	65%

methyl magnesium iodide (917-64-6) + 2,3-dichlorobenzonitrile (6574-97-6) → 2',3'-dichloroacetophenone (56041-57-7)

2,3-dichlorobenzonitrile (6574-97-6) + methylmagnesium bromide (75-16-1) → 2',3'-dichloroacetophenone (56041-57-7)

2,3-Dichloro-α-methylbenzyl alcohol (54798-91-3) → 2',3'-dichloroacetophenone (56041-57-7)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 10 - 35℃; for 3h; Inert atmosphere;	6 g

2,3-dichlorobenzylaldehyde (6334-18-5) → 2',3'-dichloroacetophenone (56041-57-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 0 - 35 °C / Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 3 h / 10 - 35 °C / Inert atmosphere View Scheme

2',3'-dichloroacetophenone (56041-57-7) → 2-bromo-1-(2,3-dichlorophenyl)ethanone

Conditions	Yield
With bromine In dichloromethane at 20℃;	100%
With bromine In dichloromethane at 0 - 20℃;	100%
With bromine In chloroform at 20℃;
With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 40℃; Darkness;

2',3'-dichloroacetophenone (56041-57-7) → 2-chloro-1-(2,3-dichlorophenyl)-ethanone (182913-78-6)

Conditions	Yield
With sulfuryl dichloride In tetrachloromethane at 20 - 45℃; for 120h;	95%

2',3'-dichloroacetophenone (56041-57-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → C11H11Cl2NO

Conditions	Yield
Heating;	90%

2',3'-dichloroacetophenone (56041-57-7) + 2,4-dichlorothiazole-5-carboxaldehyde (92972-48-0) → (E)-1-(2,3-dichlorophenyl)-3-(2,4-dichlorothiazol-5-yl)prop-2-en-1-one

Conditions	Yield
With hydrogenchloride; acetic acid In ethanol Reflux;	76%

2',3'-dichloroacetophenone (56041-57-7) + 3-fluoro-4-hydroxybenzaldehyde (405-05-0) → (E)-1-(2,3-dichlorophenyl)-3-(3-fluoro-4-hydroxyphenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In ethanol at 120℃;	72%

n-Amyl nitrite (463-04-7) + 2',3'-dichloroacetophenone (56041-57-7) → 2,3-dichlorophenylglyoxal aldoxime (94213-22-6)

Conditions	Yield
With hydrogenchloride In diethyl ether	46%

3-methoxy-4-methoxymethoxy-benzaldehyde (5533-00-6) + 2',3'-dichloroacetophenone (56041-57-7) → C18H16Cl2O4

Conditions	Yield
With barium hydroxide monohydrate In ethanol at 20℃; for 20h; Claisen-Schmidt Condensation;	41%

formaldehyd (50-00-0) + 2',3'-dichloroacetophenone (56041-57-7) + N,N-dimethylammonium chloride (506-59-2) → 1-(2,3-dichlorophenyl)-3-(dimethylamino)prop-1-one

Conditions	Yield
With hydrogenchloride In ethanol; water at 80℃; for 16h;	33.52%

1-bromo-4-methoxy-benzene (104-92-7) + 2',3'-dichloroacetophenone (56041-57-7) → 1-(2,3-dichlorophenyl)-2-(4-methoxyphenyl)ethanone (1071784-26-3)

Conditions	Yield
Stage #1: 1-bromo-4-methoxy-benzene With potassium hexamethylsilazane; 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2',3'-dichloroacetophenone In tetrahydrofuran at 20℃; for 3h; Heating / reflux;	18%

2',3'-dichloroacetophenone (56041-57-7) → 1-ethyl-2,3-dichloro-benzene (54484-61-6)

Conditions	Yield
(reduction);

2',3'-dichloroacetophenone (56041-57-7) → 1-(2',3'-dichlorophenyl)ethylamine

Conditions	Yield
(i) HCONH2, HCO2H, (ii) aq. HCl; Multistep reaction;

2',3'-dichloroacetophenone (56041-57-7) + 2-chloro-4-methyl-phenol sodium salt → 1-[3-Chloro-2-(2-chloro-4-methyl-phenoxy)-phenyl]-ethanone

Conditions	Yield
With 2-chloro-p-cresol; copper at 120 - 125℃; for 24h;

Dimethyl oxalate (553-90-2) + 2',3'-dichloroacetophenone (56041-57-7) → (Z)-4-(2,3-Dichloro-phenyl)-2-hydroxy-4-oxo-but-2-enoic acid methyl ester

Conditions	Yield
With sodium methylate In methanol at 0 - 20℃;

2',3'-dichloroacetophenone (56041-57-7) + dialkyl oxalate (R=Me or Et) → 4-(2,3-dichloro-phenyl)-2,4-dioxo-butyric acid

Conditions	Yield
Stage #1: 2',3'-dichloroacetophenone; dialkyl oxalate (R=Me or Et) With sodium methylate In tetrahydrofuran; methanol at 20℃; for 2h; Claisen condensation; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol for 4h;

2',3'-dichloroacetophenone (56041-57-7) → (S)-(-)-1-(2,3-dichlorophenyl)ethanol + (R)-(+)-1-(2,3-dichlorophenyl)ethanol

Conditions	Yield
With potassium tert-butylate; hydrogen; chiral ruthenium(II) complex In isopropyl alcohol at 0℃; under 60004.8 Torr; for 10h; Title compound not separated from byproducts;

2',3'-dichloroacetophenone (56041-57-7) → C16H12Cl2N2

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Heating 2: 46 percent / NaOAc / H2O; methanol / 90 °C View Scheme

2',3'-dichloroacetophenone (56041-57-7) → C16H12Cl2N2

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Heating 2: 6 percent / NaOAc / H2O; methanol / 90 °C View Scheme

2',3'-dichloroacetophenone (56041-57-7) → (Z)-2-Amino-4-(2,3-dichloro-phenyl)-4-oxo-but-2-enoic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOMe / methanol / 0 - 20 °C 2: NH4OAc; gl. AcOH / benzene / 12 h / Heating 3: aq. KOH / tetrahydrofuran / 0 - 20 °C View Scheme

2',3'-dichloroacetophenone (56041-57-7) → (Z)-2-Amino-4-(2,3-dichloro-phenyl)-4-oxo-but-2-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOMe / methanol / 0 - 20 °C 2: NH4OAc; gl. AcOH / benzene / 12 h / Heating View Scheme

2',3'-dichloroacetophenone (56041-57-7) → (Z)-4-(2,3-Dichloro-phenyl)-2-hydroxy-4-oxo-but-2-enoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOMe / methanol / 0 - 20 °C 2: aq. HCl / 4 h / 20 °C View Scheme

2',3'-dichloroacetophenone (56041-57-7) → [3-Chloro-2-(2-chloro-4-methyl-phenoxy)-phenyl]-acetic acid (86308-73-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2-chloro-4-methylphenol, copper / 24 h / 120 - 125 °C 2: sulfur / 24 h / Heating 3: KOH / methanol / 72 h / Heating View Scheme

2',3'-dichloroacetophenone (56041-57-7) → 2-[3-Chloro-2-(2-chloro-4-methyl-phenoxy)-phenyl]-1-morpholin-4-yl-ethanethione

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-chloro-4-methylphenol, copper / 24 h / 120 - 125 °C 2: sulfur / 24 h / Heating View Scheme

2',3'-dichloroacetophenone (56041-57-7) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-3-(2,3-dichlorophenyl)-but-2-enoic acid ethyl ester (1101067-94-0)

Conditions	Yield
With ammonium acetate; acetic acid In benzene

2',3'-dichloroacetophenone (56041-57-7) + (1-trityl-1H-imidazol-4-yl)magnesium bromide (184579-26-8) → 1-(2,3-dichloro-phenyl)-1-(1-trityl-1H-imidazol-4-yl)-ethanol (881409-76-3)

Conditions	Yield
Stage #1: 2',3'-dichloroacetophenone; (1-trityl-1H-imidazol-4-yl)magnesium bromide In dichloromethane at 20℃; for 16h; Stage #2: With ammonium chloride In dichloromethane

2',3'-dichloroacetophenone (56041-57-7) + toluene-4-sulfonic acid (104-15-4) + ethylene glycol (107-21-1) → 2-(bromomethyl)-2-(2,3-dichlorophenyl)-1,3-dioxolane

Conditions	Yield
With bromine In di-isopropyl ether; butan-1-ol; benzene	96.6 parts (49%)

Upstream product

• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 54798-91-3 2,3-Dichloro-α-methylbenzyl alcohol 
• 95-50-1 1,2-dichloro-benzene 
• 6574-97-6 2,3-dichlorobenzonitrile 
• 75-16-1 methylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 54484-61-6 2,3-Dichlorethylbenzol 
• 39226-94-3 1-(2',3'-dichlorophenyl)ethylamine 
• 158397-38-7 2,3-dichlorophenyloxirane 
• 1394858-94-6 3-(2-(benzyloxy)-1-(2,3-dichlorophenyl)ethyl)-1-methyl-1-(1-methylpiperidine-4-yl)urea 
• 1394860-41-3 C₈H₇BrCl₂O 
• 1394860-42-4 C₁₅H₁₄Cl₂O₂ 
• 1394860-43-5 C₂₃H₁₇Cl₂NO₃ 
• 1394860-44-6 C₁₅H₁₅Cl₂NO 

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