2648-61-5

Basic information

• Product Name: 2,2-DICHLOROACETOPHENONE
• Synonyms: 2,2-dichloro-acetophenon;Acetophenone, 2,2-dichloro-;Ethanone, 2,2-dichloro-1-phenyl-;Ethanone,2,2-dichloro-1-phenyl-;omega,omega-Dichloroacetophenone;alpha,alpha-Dichloroacetophenone,97%;à,à-dichloroacetophenone;(Dichloroacetyl)benzene
• CAS NO: 2648-61-5
• Molecular Formula: C₈H₆Cl₂O
• Molecular Weight: 189.04
• EINECS: 202-783-6
• Product Categories: C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 2648-61-5.mol
• Article Data: 84

Chemical Properties

• Melting Point: 20-21 °C(lit.)
• Boiling Point: 132-134 °C13 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.34 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0194mmHg at 25°C
• Refractive Index: n20/D 1.5686(lit.)
• BRN: 1864186
• CAS DataBase Reference: 2,2-DICHLOROACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DICHLOROACETOPHENONE(2648-61-5)
• EPA Substance Registry System: 2,2-DICHLOROACETOPHENONE(2648-61-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38
• Safety Statements: 26-27-28-36/37/39-7/9
• RIDADR: UN 2810 6.1/PG 2
• WGK Germany: 3
• RTECS: AM7175000
• TSCA: Yes
• PackingGroup: II
• Hazardous Substances Data: 2648-61-5(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY PINK LIQUID

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 527, 1983 DOI: 10.1016/S0040-4039(00)81455-0

InChI:InChI=1/C8H6Cl2O/c9-8(10)7(11)6-4-2-1-3-5-6/h1-5,8H

Synthetic route

N-(2,2-dichloro-3-oxo-1,3-diphenylpropyl)phenylsulfonamide (907563-74-0) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; water at 20℃; for 4h; retro-aldol reaction;	100%

acetophenone (98-86-2) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With chlorine In methanol at 40℃; under 760.051 - 1520.1 Torr; Solvent; Temperature;	99.1%
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; N-chloro-succinimide at 70℃; Green chemistry;	96%
With chlorine In acetic acid at 51 - 56℃; for 4.5h;	95.5%

phenylacetylene (536-74-3) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With Oxone; potassium chloride In water; acetonitrile at 20℃; for 0.166667h; Reagent/catalyst;	98%
With trichloroisocyanuric acid; p-methylphenylthiourea; water at 20℃; for 0.333333h; Reagent/catalyst; Temperature; Sealed tube; Sonication; Green chemistry; chemoselective reaction;	92%
With hydrogenchloride; sulfuric acid; lithium perchlorate In water; acetonitrile at 10 - 20℃; for 4.25h; Mechanism; Reagent/catalyst; Electrochemical reaction; Electrolysis; Green chemistry;	92%

2,2,2-trichloroacetophenone (2902-69-4) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With methanol; triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Appel Halogenation; Inert atmosphere; chemoselective reaction;	97%
With 10% Pt/activated carbon; hydrogen In N,N-dimethyl acetamide at 25℃; under 760.051 Torr; for 0.7h; Catalytic behavior; chemoselective reaction;	89%
With palladium 10% on activated carbon; hydrogen In N,N-dimethyl acetamide at 25℃; under 760.051 Torr; for 0.7h; chemoselective reaction;	88%

dichloromethane (75-09-2) + N-methoxy-N-methylbenzamide (6919-61-5) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With methyllithium lithium bromide; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; chemoselective reaction;	90%

2,4-Xylidine (95-68-1) + benzoyl(dichloro)acetaldehyde (160663-32-1) → 2,2-dichloroacetophenone (2648-61-5) + N-(2,4-dimethylphenyl)formamide (60397-77-5)

Conditions	Yield
In tetrachloromethane for 12h; Ambient temperature;	A 80% B 89%

benzoyl(dichloro)acetaldehyde (160663-32-1) → 2,2-dichloroacetophenone (2648-61-5) + N-(2,4-dimethylphenyl)formamide (60397-77-5)

Conditions	Yield
With 2,4-Xylidine In tetrachloromethane for 12h; Ambient temperature;	A 80% B 89%

1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With trichloroisocyanuric acid; p-methylphenylthiourea; water at 20℃; for 0.333333h; Sealed tube; Sonication; Green chemistry; chemoselective reaction;	88%

2-(dimethyl(oxo)-λ6-sulfaneylidene)-1-phenylethan-1-one (20718-17-6) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With trichloroisocyanuric acid; tetrabutyl-ammonium chloride In tetrahydrofuran at 0 - 25℃; for 24h; Sealed tube;	87%

acetophenone (98-86-2) → 2,2-dichloroacetophenone (2648-61-5) + 1-chloroacetophenone (532-27-4)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide In ethanol at 91 - 93℃; for 0.25h; Product distribution; Further Variations:; Solvents; Temperatures; time;	A 85% B 4.5%
With N-chloro-succinimide; 1-(n-butyl)-3-methylimidazolium triflate at 70℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Concentration; Green chemistry;	A n/a B 74%
With N-chloro-succinimide; toluene-4-sulfonic acid at 20℃; for 24h;	A 4% B 70%

3-oxo-3-phenylpropanamide (3446-58-0) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate In tetrahydrofuran at 80℃; for 4h; Reagent/catalyst; Time; Solvent; Temperature; Concentration;	83%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; potassium tert-butylate In tetrahydrofuran at 80℃; for 4h; Reagent/catalyst; Solvent; Temperature;	83%
Multi-step reaction with 2 steps 1: N-chloro-succinimide / methanol / 5 h / 20 °C 2: N-chloro-succinimide; potassium tert-butylate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / tetrahydrofuran / 4 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: N-chloro-succinimide / methanol / 5 h / 20 °C 2: potassium tert-butylate / tetrahydrofuran / 4 h / 80 °C View Scheme

1-iodo-2-phenylethyne (932-88-7) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With iodine; sodium chloride In dimethyl sulfoxide at 20℃; for 4h;	81%

2,2-dichloro-1-phenyl-2-(phenylsulfinyl)-1-ethanol (86002-02-0) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
In neat (no solvent) at 150℃; under 1 Torr; for 0.0833333h;	80%

1-phenyl-3-dimethylaminoprop-2-enone (1201-93-0) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With N-chloro-succinimide; dibenzoyl peroxide In para-xylene at 60℃; for 12h;	80%

1-Phenylethanol (98-85-1, 13323-81-4) → 2,2-dichloroacetophenone (2648-61-5) + 1-chloroacetophenone (532-27-4) + acetophenone (98-86-2)

Conditions	Yield
With methanol; trichloroisocyanuric acid In dichloromethane at 20℃; for 5h;	A 10 %Chromat. B 78% C 8 %Chromat.

phenylacetylene (536-74-3) → 2,2-dichloroacetophenone (2648-61-5) + 1-chloroacetophenone (532-27-4)

Conditions	Yield
With iodine; sodium chloride In dimethyl sulfoxide at 20℃; for 4h;	A 78% B 9%
With hydrogenchloride; iodine In dimethyl sulfoxide at 20℃; for 16h;	A 19% B 73%

2-chloro-3-oxo-3-phenylpropanamide → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate In tetrahydrofuran at 80℃; for 4h; Reagent/catalyst;	77%

(2,2-Dichloro-1-ethoxy-vinyl)-benzene (78176-13-3) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With trifluoroacetic acid In water at 65℃; for 7h;	76%

2,2-dichloro-1-phenylethanol (2612-36-4) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In tert-butyl methyl ether at 20℃; under 760.051 Torr; for 24h; Kinetics; Thermodynamic data; Concentration; pH-value; Reagent/catalyst; Solvent; Temperature; Time; Enzymatic reaction;	76%

α-Phenyl-β,β-dichlorvinyl-methylether (27904-75-2) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With sulfuric acid In 1,4-dioxane; water Heating;	75%

methanol (67-56-1) + benzaldehyde (100-52-7) → 2,2-dichloroacetophenone (2648-61-5) + α-chloroacetophenone dimethyl acetal (33604-55-6)

Conditions	Yield
With piperidine; 1,3-dichloro-5,5-dimethylhydantoin for 12h; Molecular sieve; Reflux;	A 7 %Spectr. B 72%

C9H7Cl2NO2 → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 80℃; for 4h; Reagent/catalyst;	71%

1-Phenyl-4,4,4-trifluorobutane-1,3-dione (326-06-7) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With N-chloro-N-methoxybenzenesulfonamide; potassium carbonate In acetonitrile at 20℃;	70%

benzoic acid methyl ester (93-58-3) + dichloromethane (75-09-2) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With lithium dicyclohexylamide In tetrahydrofuran at -78℃; for 0.333333h;	66%

N-(2,2-Dichloro-1-hydroxy-3-oxo-3-phenyl-propyl)-acetamide (184970-72-7) → acetamide (60-35-5) + 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With sodium hydroxide In ethanol for 12h; Ambient temperature;	A n/a B 60%

N-(2,2-Dichloro-1-hydroxy-3-oxo-3-phenyl-propyl)-benzamide (184970-73-8) → 2,2-dichloroacetophenone (2648-61-5) + benzamide (55-21-0)

Conditions	Yield
With sodium hydroxide In ethanol for 12h; Ambient temperature;	A 60% B n/a

dichloroacethyl chloride (79-36-7) + benzene (71-43-2) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With aluminium trichloride for 3h; Ambient temperature;	55.2%
With aluminium trichloride

2,2,2-trichloroacetophenone (2902-69-4) + lithium thiophenoxide (2973-86-6) → 2,2-dichloroacetophenone (2648-61-5) + ω,ω-bis(phenylthio)acetophenone (22805-27-2)

Conditions	Yield
In tetrahydrofuran at -78℃; for 0.166667h;	A 40% B 50%

α-bromoacetophenone (70-11-1) → 2,2-dichloroacetophenone (2648-61-5)

Conditions	Yield
With antimonypentachloride In tetrachloromethane for 8h; Heating;	47%

benzoyl(dichloro)acetaldehyde (160663-32-1) + sodium 1-propanethiolate (6898-84-6) → 2,2-dichloroacetophenone (2648-61-5) + 3-chloro-1-phenyl-3-propylthio-1,2-propanedione

Conditions	Yield
In diethyl ether for 1h; Heating;	A 40% B 40%

2,2-dichloroacetophenone (2648-61-5) + 4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane (167773-10-6) → (R)-1,1-dichloro-4-methyl-2-phenylpent-4-en-2-ol

Conditions	Yield
With methanol; (S)-N-(3-(tert-butyl)-2-hydroxybenzyl)-1-(dimethylamino)-3-methyl-1-oxobutan-2-aminium; zinc dimethoxide In toluene at -40℃; for 18h; Inert atmosphere; Glovebox; enantioselective reaction;	98%

2,2-dichloroacetophenone (2648-61-5) + isovaleraldehyde (590-86-3) → (E)-5-methyl-1-phenyl-hex-2-en-1-one (15175-34-5)

Conditions	Yield
With chromium dichloride In tetrahydrofuran for 2h; Heating;	97%

furfural (98-01-1) + 2,2-dichloroacetophenone (2648-61-5) → Furfuralacetophenon (22488-76-2)

Conditions	Yield
With chromium dichloride In tetrahydrofuran for 2h; Heating;	96%

methanol (67-56-1) + 2,2-dichloroacetophenone (2648-61-5) → 2,2-dimethoxy-1-phenylethanone (6956-56-5)

Conditions	Yield
With sodium carbonate at 80℃; for 12h; Green chemistry;	96%

methanol (67-56-1) + 2,2-dichloroacetophenone (2648-61-5) → phenylglyoxal dimethylacetal (19159-39-8)

Conditions	Yield
With sodium methylate for 4h; Ambient temperature;	95%
With sodium methylate Ambient temperature;	51%

2,2-dichloroacetophenone (2648-61-5) → 2,2,2-trichloroacetophenone (2902-69-4)

Conditions	Yield
With manganese triacetate; lithium chloride In acetic acid for 3.5h; Product distribution; Mechanism; Heating; without LiCl; other time and molar ratio;;	95%
	94%

2,2-dichloroacetophenone (2648-61-5) + phenylacetaldehyde (122-78-1) → (E)-1,4-diphenylbut-2-en-1-one (34587-61-6)

Conditions	Yield
With chromium dichloride In tetrahydrofuran for 2h; Heating;	95%

2-Methylbutyraldehyde (96-17-3, 57456-98-1) + 2,2-dichloroacetophenone (2648-61-5) → (E)-4-Methyl-1-phenyl-hex-2-en-1-one

Conditions	Yield
With chromium dichloride In tetrahydrofuran for 2h; Heating;	94%

2,2-dichloroacetophenone (2648-61-5) → -α-(Dichlormethyl)benzolmethanol

Conditions	Yield
With trimethylaluminum; C44H42O2; isopropyl alcohol In pentane at -10℃; for 24h; Meerwein-Ponndorf-Verley Reduction; Molecular sieve; enantioselective reaction;	94%
With alcohol dehydrogenase from Lactobacillus brevis; isopropyl alcohol In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 48h; pH=7.5; Kinetics; Enzymatic reaction; enantioselective reaction;	n/a
With alcohol dehydrogenase from Lactobacillus brevis; NADPH; magnesium chloride In isopropyl alcohol at 30℃; for 24h; pH=7.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	n/a
With glucose dehydrogenase; D-Glucose; Sporobolomyces salmonicolor carbonyl reductase S224A; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer; dimethyl sulfoxide at 20℃; pH=7; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	n/a

3-Bromopyridine (626-55-1) + 2,2-dichloroacetophenone (2648-61-5) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 9-bromo-2-(dichloromethyl)-2-phenyl-2H,9aH-pyrido[2,1-b][1,3]oxazine-3,4-dicarboxylate (1401312-79-5)

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; stereoselective reaction;	93%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 2,2-dichloroacetophenone (2648-61-5) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 5-(tert-butylimino)-2-(dichloromethyl)-2-phenyl-2,5-dihydrofuran-3,4-dicarboylate (1379588-53-0)

Conditions	Yield
In dichloromethane at 20℃; for 1h; chemoselective reaction;	92%

2,2-dichloroacetophenone (2648-61-5) + 4-nitrobenzaldehdye (555-16-8) → ((2RS,3RS)-2-chloro-3-(4-nitrophenyl)oxiran-2-yl)(phenyl)methanone

Conditions	Yield
Stage #1: 2,2-dichloroacetophenone With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Stage #2: 4-nitrobenzaldehdye In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;	92%

dmap (1122-58-3) + 2,2-dichloroacetophenone (2648-61-5) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 1-benzoyl-7-(dimethylamino)indolizine-2,3-dicarboxylate

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h; chemoselective reaction;	92%

isoquinoline (119-65-3) + 2,2-dichloroacetophenone (2648-61-5) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 2-(dichloromethyl)-2-phenyl-2H,11bH-[1,3]oxazino[2,3-a]isoquinoline-3,4-dicarboxylate

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; for 4h; diastereoselective reaction;	92%

2,2-dichloroacetophenone (2648-61-5) + 2-Phenylpropanal (34713-70-7) → (E)-(4RS)-1,4-diphenylpent-2-en-1-one (114245-62-4)

Conditions	Yield
With chromium dichloride In tetrahydrofuran for 2h; Heating;	91%

3-Chloropyridine (626-60-8) + 2,2-dichloroacetophenone (2648-61-5) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 9-chloro-2-(dichloromethyl)-2-phenyl-2H,9aH-pyrido[2,1-b][1,3]oxazine-3,4-dicarboxylate (1401312-83-1)

Conditions	Yield
In diethyl ether; dichloromethane at 20℃; stereoselective reaction;	91%

4-aminopyridine (504-24-5) + 2,2-dichloroacetophenone (2648-61-5) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 7-amino-1-benzoylindolizine-2,3-dicarboxylate

Conditions	Yield
In tetrahydrofuran at 20℃; chemoselective reaction;	91%

2,2-dichloroacetophenone (2648-61-5) → phenacylacetophenone (495-71-6)

Conditions	Yield
With indium(I) bromide In tetrahydrofuran at 20℃; for 24h;	90%

Octanal (124-13-0) + 2,2-dichloroacetophenone (2648-61-5) → (E)‐1‐phenyldec‐2‐en‐1‐one

Conditions	Yield
With chromium dichloride In tetrahydrofuran for 2h; Heating;	90%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 2,2-dichloroacetophenone (2648-61-5) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 5-(tert-butylimino)-2-(dichloromethyl)-2-phenyl-2,5-dihydrofuran-3,4-dicarboxylate (1379588-52-9)

Conditions	Yield
In dichloromethane at 20℃; for 1h; chemoselective reaction;	90%

dmap (1122-58-3) + 2,2-dichloroacetophenone (2648-61-5) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 1-benzoyl-7-(dimethylamino)indolizine-2,3-dicarboxylate

Conditions	Yield
In tetrahydrofuran at 20℃; chemoselective reaction;	90%

2,2-dichloroacetophenone (2648-61-5) → 2,2-dichloro-1-phenylethanol (2612-36-4)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In ethanol -> 28 deg C (10 min.), 10 min.;	88.1%
With formic acid; 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; sodium formate In water at 80℃; for 18h; pH=4.5; Inert atmosphere; chemoselective reaction;	87%
With sodium tetrahydroborate In ethanol at 20 - 22℃; for 17.33h; Cooling with ice;	73%

Upstream product

• 79-43-6 dichloro-acetic acid 
• 2000-43-3 2,2,2-trichloro-1-phenylethanol 
• 56-23-5 tetrachloromethane 
• 624-85-1 ethyl hypochlorite 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 79-36-7 dichloroacethyl chloride 
• 71-43-2 benzene 
• 3018-12-0 dichloroacetonitrile 
• 93-89-0 benzoic acid ethyl ester 
• 2146-67-0 (dichloromethyl)lithium 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 2648-66-0 α,α-Dichloroacetophenone dimethyl acetal 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 54824-08-7 2,2-dichloro-3-hydroxy-1-phenylpropan-1-one 
• 2612-36-4 2,2-dichloro-1-phenylethanol 
• 75-27-4 bromodichloromethane 
• 395-01-7 2,2-difluoro-1-phenylethanone 
• 19159-39-8 phenylglyoxal dimethylacetal 
• 19676-39-2 (1,1,2,2-tetrachloro-ethyl)-benzene 
• 27700-44-3 2,2-dichloro-1-(3-nitrophenyl)ethan-1-one 
• 74966-68-0 2,2-diiodo-1-phenylethan-1-one 
• 611-71-2 MANDELIC ACID 
• 40731-59-7 phosphoric acid diethyl ester-(2-chloro-1-phenyl-vinyl ester) 
• 26346-87-2 2-Bromo-2,2-dichloro-1-phenyl-ethanone 
• 5955-86-2 Phenylglyoxylsaeurethionethylamid 
• 27970-76-9 Methanesulfonic acid 2,2-dichloro-1-phenyl-vinyl ester 
• 40991-71-7 ω,ω-Bis-dimethylamino-acetophenon 

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