6084-17-9

Basic information

• Product Name: 2-Chloropropiophenone
• Synonyms: 2-CHLOROPROPIOPHENONE;2-CHLORO-1-PHENYL-1-PROPANONE;2-CHLORO-1-PHENYLPROPAN-1-ONE;1-Propanone, 2-chloro-1-phenyl- (9CI);1-Propanone,2-chloro-1-phenyl-
• CAS NO: 6084-17-9
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.62
• EINECS: 230-330-2
• Product Categories: ACETYLHALIDE
• Mol File: 6084-17-9.mol
• Article Data: 40

Chemical Properties

• Melting Point: 213-214 °C
• Boiling Point: 241.8ºC at 760 mmHg
• Flash Point: 118.4ºC
• Appearance: /
• Density: 1.129g/cm3
• Vapor Pressure: 0.0351mmHg at 25°C
• Refractive Index: 1.5430-1.5470
• CAS DataBase Reference: 2-Chloropropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloropropiophenone(6084-17-9)
• EPA Substance Registry System: 2-Chloropropiophenone(6084-17-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 6084-17-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 28, p. 630, 1963 DOI: 10.1021/jo01038a007

InChI:InChI=1/C9H9ClO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,1H3/t7-/m1/s1

Synthetic route

1-phenyl-propan-1-one (93-55-0) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
Stage #1: 1-phenyl-propan-1-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: With methyl chlorosulfate In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;	100%
With chloro-trimethyl-silane; tetrabutylammomium bromide; dimethyl sulfoxide In acetonitrile for 5h;	94%
With sulfuryl dichloride for 2h; Ambient temperature;	93%

1-phenylpropene (637-50-3) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With magnesium(II) chloride hexahydrate; cobalt(II) chloride hexahydrate; sulfuric acid; oxygen; lithium perchlorate In dichloromethane; acetone at 40℃; for 11h; Electrolysis; Sealed tube; chemoselective reaction;	95%
With magnesium(II) chloride hexahydrate; oxygen; lithium perchlorate; manganese(ll) chloride In dichloromethane; acetone at 40℃; for 40h; Electrochemical reaction;	92%
With oxygen; iron(III) chloride In pyridine; tetrachloromethane for 0.5h; Irradiation;	66%

1-Phenyl-1-propanol (93-54-9) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With N,N-dichloro-p-toluenesulfonamide In acetonitrile at 35℃; for 1h;	94%
With N,N-dichloro-p-toluenesulfonamide In acetonitrile at 40℃; for 1.5h; solvent effects for the synthesis α-chloro ketones; reactions with the solvents CCl4, THF, and pyridine. Oxychlorination of other secondary alcohols in acetonitrile.;	94%
With methanol; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at 20℃; for 2h; Reagent/catalyst;	88%

(Z)-(1-Chloro-1-propenyl)benzene (4541-85-9) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With [hydroxy(tosyloxy)iodo]benzene; water; toluene-4-sulfonic acid In acetonitrile at 20℃; for 20h;	94%

2-bromo-1-phenyl-1-propanone (2114-00-3) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With S4N4*SbCl5 In toluene for 9h; Heating;	88%
With potassium chloride In ethanol at 82.5℃; under 725 Torr; Equilibrium constant;
With hydrogenchloride In ethanol

1-Phenyl-2-propen-1-ol (4393-06-0) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With N-chloro-succinimide; [{Cp*IrCl2}]2 In tetrahydrofuran; water at 20℃; for 20h;	80%

(Z)-tert-butyldimethyl((1-phenylprop-1-en-1-yl)oxy)silane (95837-63-1) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With samarium(III) trifluoromethanesulfonate In tetrahydrofuran; dichloromethane at -78℃; for 0.166667h;	76%

2-(dimethyl(oxo)-λ6-sulfaneylidene)-1-phenylethan-1-one (20718-17-6) + methyl iodide (74-88-4) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With tetrabutyl-ammonium chloride In acetonitrile at 25℃; for 24h; Sealed tube;	66%

1-phenyl-propan-1-one (93-55-0) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 2-phenylpropionic acid methyl ester (31508-44-8)

Conditions	Yield
With iodine trichloride; trimethyl orthoformate at 23℃; for 24h;	A 26% B 62%

propiophenone dimethyl acetal (25310-92-3) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 2-phenylpropionic acid methyl ester (31508-44-8)

Conditions	Yield
With iodine trichloride; trimethyl orthoformate at 23℃; for 24h;	A 32% B 55%

α-tosyloxypropiophenone (87456-64-2) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With hydrogenchloride In [D3]acetonitrile at 20℃; for 36h;	35%

1-phenyl-1-trimethylsiloxypropene (37471-46-8) + trifluoromethane sulfonyl chloride (421-83-0) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 3,3,3-trifluoro-2-methyl-1-phenylpropan-1-one (128271-44-3)

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride In benzene at 120℃; for 7h;	A 19% B 28%

1-phenyl-1-trimethylsiloxypropene (37471-46-8) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 3,3,3-trifluoro-2-methyl-1-phenylpropan-1-one (128271-44-3)

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride; trifluoromethane sulfonyl chloride In benzene at 120℃; for 7h;	A 19% B 28%

(Z)-9-(1-phenylprop-1-enyloxy)-9-borabicyclo[3.3.1]nonane (120331-99-9) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 2,3-dimethyl-1,4-diphenyl-butane-1,4-dione (34733-55-6) + (2R*,3S*)-2,3-dimethyl-1,4-diphenylbutane-1,4-dione (73893-85-3)

Conditions	Yield
With vanadium (V) oxide dichloride ethanolate at 20℃; for 2h; Time; Inert atmosphere; Glovebox; diastereoselective reaction;	A 13% B n/a C n/a

2-chloro-2-morpholin-4-ylsulfanyl-1-phenyl-propan-1-one (63369-87-9) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With hydrogenchloride

chloro-2-phenyl-2-methyl-3-oxiranne (Z) (6202-57-9, 22377-79-3) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
at 140℃;

2-chloropropionyl chloride (7623-09-8) + benzene (71-43-2) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With aluminium trichloride
With aluminum (III) chloride at 0 - 30℃; for 4h; Time; Friedel-Crafts Acylation; Inert atmosphere;

2-Chlor-3-methyl-2-phenyloxiran (6202-57-9) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 1-fluoroethyl phenyl ketone (21120-36-5)

Conditions	Yield
With silver tetrafluoroborate In diethyl ether 1) -30 deg C, 5 min, 2) r.t., 30 min; Yield given. Yields of byproduct given;

1-Phenyl-1-propanol (93-54-9) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 1-phenyl-propan-1-one (93-55-0)

Conditions	Yield
In benzene for 24h; Irradiation; Yield given. Yields of byproduct given;

benzoyl chloride (98-88-4) + (R,S)-2-chloropropionic acid (598-78-7) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With lithium diisopropyl amide 1.) THF, hexane, -80 deg C, 5 min., 2.) THF, hexane, -80 deg C --> room temp.; Yield given. Multistep reaction;

chloro-2-phenyl-2-methyl-3-oxiranne (Z) (6202-57-9, 22377-79-3) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 1-fluoroethyl phenyl ketone (21120-36-5)

Conditions	Yield
With F In tetrahydrofuran 1.) -70 deg C; 2.) RT, 1h; Yield given;

[(2-chloro-2-propenyl)-oxo]benzene (19233-44-4) + n-butylmercuric chloride (543-63-5) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 2-Chloro-1-phenyl-heptan-1-one (143427-03-6)

Conditions	Yield
With sodium thiosulfate; HSiPh3 1.) DMSO, 3 h, 2.) DMSO; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

[(2-chloro-2-propenyl)-oxo]benzene (19233-44-4) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 2-Chloro-1-phenyl-heptan-1-one (143427-03-6)

Conditions	Yield
With n-butylmercuric chloride; sodium thiosulfate; HSiPh3 1.) DMSO, 3 h, 2.) DMSO; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

2-iodo-1-phenylpropan-1-one (6084-15-7) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With potassium chloride In ethanol at 82.5℃; under 725 Torr; Equilibrium constant;
With aluminum (III) chloride; ammonium metavanadate; oxygen; tetra-(n-butyl)ammonium iodide In acetonitrile at 80℃; for 24h;	92 %Spectr.

trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane (66323-99-7) → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With pyridine; tert.-butylhydroperoxide; titanium(IV) dichlorodiisopropylate; 3 A molecular sieve 1) THF, CH2Cl2, r.t., 45 min, 2) THF, CH2Cl2, -50 deg C, 1 h, r.t., 12 h; Yield given; Multistep reaction;

benzene (71-43-2) + (+-)-2-chloro-propionic acid-chloride → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
With aluminium trichloride

1-phenyl-propan-1-one (93-55-0) + bis → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran / -60 - 0 °C 2: 1) pyridine, molecular sieves 3 Angstroem, TiCl2(OiPr)2, 2) tBuOOH / 1) THF, CH2Cl2, r.t., 45 min, 2) THF, CH2Cl2, -50 deg C, 1 h, r.t., 12 h View Scheme

1-phenyl-propan-1-one (93-55-0) + /PCCWF195-1820/ → 2-chloro-1-phenylpropan-1-one (6084-17-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 36 percent / Et3N / dimethylformamide / 48 h / Heating 2: 19 percent / RuCl2(PPh3)3 / benzene / 7 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: 36 percent / Et3N / dimethylformamide / 48 h / Heating 2: 19 percent / RuCl2(PPh3)3, CF3SO2Cl / benzene / 7 h / 120 °C View Scheme

Phenyl vinyl ketone (768-03-6) → 2-chloro-1-phenylpropan-1-one (6084-17-9) + 2,3-dimethyl-1,4-diphenyl-butane-1,4-dione (34733-55-6) + (2R*,3S*)-2,3-dimethyl-1,4-diphenylbutane-1,4-dione (73893-85-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 9-bora-bicyclo[3.3.1]nonane / chloroform-d1; tetrahydrofuran / 2 h / 20 °C / Molecular sieve; Inert atmosphere; Glovebox 2: vanadium (V) oxide dichloride ethanolate / 2 h / 20 °C / Inert atmosphere; Glovebox View Scheme

2-chloro-1-phenylpropan-1-one (6084-17-9) + 2,6-dimethyl-1,5-dihydroxynaphthalene (123979-29-3) → 2,6-Dimethyl-1,5-bis(1-oxo-1-phenyl-2-propoxy)naphthalene (137517-24-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;	100%

2-chloro-1-phenylpropan-1-one (6084-17-9) + thiophenol (108-98-5) → 1-phenyl-2-(phenylthio)propan-1-one (28403-86-3)

Conditions	Yield
Stage #1: thiophenol With ethanol; sodium for 0.333333h; Inert atmosphere; Stage #2: 2-chloro-1-phenylpropan-1-one In ethanol at 20℃; for 16h; Inert atmosphere;	97%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane for 12h;	78%

2-chloro-1-phenylpropan-1-one (6084-17-9) → 1-fluoroethyl phenyl ketone (21120-36-5)

Conditions	Yield
With pyridine; tetrabutyl ammonium fluoride In 1,4-dioxane at 80℃; for 24h;	95%
With potassium hydrogenfluoride In diethylene glycol Heating;
With pyridine; hydrogen fluoride; mercury(II) oxide

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 2-chloro-1-phenylpropan-1-one (6084-17-9) → C13H15O2Cl

Conditions	Yield
With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 20h; Horner-Wadsworth-Emmons olefination;	95%

2-chloro-1-phenylpropan-1-one (6084-17-9) + dimethyl amine (124-40-3) → metamfepramone (15351-09-4)

Conditions	Yield
In benzene for 96h; Ambient temperature;	91%

2-chloropyrimidin-4-amine (7461-50-9) + 2-chloro-1-phenylpropan-1-one (6084-17-9) → 5-chloro-3-methyl-2-phenylimidazolo[1,2-c]pyrimidine

Conditions	Yield
In toluene at 60℃; for 20h;	91%

2-chloro-1-phenylpropan-1-one (6084-17-9) + allyltributylstanane (24850-33-7) → 2-Chloro-3-phenyl-hex-5-en-3-ol

Conditions	Yield
With tin(ll) chloride In acetonitrile at 25℃; for 0.25h;	90%

2-chloro-1-phenylpropan-1-one (6084-17-9) → 2-mercapto-1-phenylpropan-1-one (13792-77-3, 140237-90-7, 140237-91-8)

Conditions	Yield
With sodium hydrogensulfide In methanol; diethyl ether at -20℃; for 4h;	89%
With hydrogen sulfide; sodium methylate In methanol

2-chloro-1-phenylpropan-1-one (6084-17-9) + 2-methylpropan-2-thiol (75-66-1) → 2-tert-butylsulfenyl-1-phenylpropanone

Conditions	Yield
With sodium hydroxide; benzyltriethylammonium bromide In dichloromethane; water for 4.5h;	88%

2-chloro-1-phenylpropan-1-one (6084-17-9) + propionaldehyde (123-38-6) → 2,3-epoxy-2-ethyl-1-phenyl-1-propanone (99865-23-3)

Conditions	Yield
With Aliquat 336; lithium hydroxide In water at 20℃; for 4h; Darzens Condensation;	88%

2-chloro-1-phenylpropan-1-one (6084-17-9) + 1-acetoxy-1-phenylethene (2206-94-2) → 2-methyl-1,4-diphenylbutane-1,4-dione (15982-59-9)

Conditions	Yield
With dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III) In acetone at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;	87%

4-Methoxystyrene (637-69-4) + 2-chloro-1-phenylpropan-1-one (6084-17-9) → 5-(4-methoxyphenyl)-3-methyl-2-phenylfuran (1443441-67-5)

Conditions	Yield
With 2,6-dimethylpyridine; dipotassium peroxodisulfate; fac-Ir(2-phenylpyridine)3 In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;	86%

1-ethenyl-4-methylbenzene (622-97-9) + 2-chloro-1-phenylpropan-1-one (6084-17-9) → 3-methyl-2-phenyl-5-(p-tolyl)furan (1443441-65-3)

Conditions	Yield
With 2,6-dimethylpyridine; dipotassium peroxodisulfate; fac-Ir(2-phenylpyridine)3 In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;	85%

para-fluorostyrene (405-99-2) + 2-chloro-1-phenylpropan-1-one (6084-17-9) → 5-(4-fluorophenyl)-3-methyl-2-phenylfuran (1443441-68-6)

Conditions	Yield
With 2,6-dimethylpyridine; dipotassium peroxodisulfate; fac-Ir(2-phenylpyridine)3 In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;	84%

styrene (100-42-5) + 2-chloro-1-phenylpropan-1-one (6084-17-9) → 3-methyl-2,5-diphenylfuran (84302-11-4)

Conditions	Yield
With 2,6-dimethylpyridine; dipotassium peroxodisulfate; fac-Ir(2-phenylpyridine)3 In dimethyl sulfoxide at 20℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Irradiation;	84%

2-chloro-1-phenylpropan-1-one (6084-17-9) → 1-phenyl-propan-1-one (93-55-0)

Conditions	Yield
With water; zinc In acetonitrile at 80℃; for 8h; Sealed tube; Inert atmosphere;	83%
With water; zinc In acetonitrile at 80℃; for 8h; Inert atmosphere; Sealed tube;	83%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid for 4.5h; Irradiation; Inert atmosphere;	75%
With hydrogen selenide; triethylamine In methanol for 3h; Ambient temperature; Yield given;

2-chloro-1-phenylpropan-1-one (6084-17-9) → propiophenone-α-d1 (76973-09-6)

Conditions	Yield
With water-d2; zinc In acetonitrile at 80℃; for 8h; Inert atmosphere; Sealed tube;	83%
With water-d2; zinc In acetonitrile at 80℃; for 8h; Inert atmosphere; Sealed tube;	83%

2-chloro-1-phenylpropan-1-one (6084-17-9) + benzyl-methyl-amine (103-67-3) → 2-(N-benzyl-N-methylamino)-1-phenylpropan-1-one (16735-30-1)

Conditions	Yield
With triethylamine In 1,2-dimethoxyethane Heating;	81%

5-vinyl-1,3-benzodioxole (7315-32-4) + 2-chloro-1-phenylpropan-1-one (6084-17-9) → 5-(4-methyl-5-phenylfuran-2-yl)benzo[d][1,3]dioxole (1443441-66-4)

Conditions	Yield
With 2,6-dimethylpyridine; dipotassium peroxodisulfate; fac-Ir(2-phenylpyridine)3 In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;	81%

2-chloro-1-phenylpropan-1-one (6084-17-9) + N-benzyl-2-(piperazin-1-yl)acetamide hydrochloride (850415-38-2) → N-benzyl-2-(4-(1-oxo-1-phenylpropan-2-yl)piperazin-1-yl)acetamide

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	79%

2-chloro-1-phenylpropan-1-one (6084-17-9) + 2-Vinylnaphthalene (827-54-3) → 3-methyl-5-(naphthalene-2-yl)-2-phenylfuran

Conditions	Yield
With 2,6-dimethylpyridine; dipotassium peroxodisulfate; fac-Ir(2-phenylpyridine)3 In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;	79%

2-chloro-1-phenylpropan-1-one (6084-17-9) + 2,4,6-trimethylstyrene (769-25-5) → 5-mesityl-3-methyl-2-phenylfuran

Conditions	Yield
With 2,6-dimethylpyridine; dipotassium peroxodisulfate; fac-Ir(2-phenylpyridine)3 In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;	79%

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 63369-87-9 2-chloro-2-morpholin-4-ylsulfanyl-1-phenyl-propan-1-one 
• 6202-57-9 chloro-2-phenyl-2-methyl-3-oxiranne (Z) 
• 7623-09-8 2-chloropropionyl chloride 
• 71-43-2 benzene 
• 6202-57-9 2-Chlor-3-methyl-2-phenyloxiran 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 120331-99-9 (Z)-9-(1-phenylprop-1-enyloxy)-9-borabicyclo[3.3.1]nonane 
• 768-03-6 Phenyl vinyl ketone 
• 98-88-4 benzoyl chloride 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 74-88-4 methyl iodide 

Downstream Products

• 62366-01-2 4-phenyl-1,10-phenanthroline 
• 6640-19-3 2-phenoxy-1-phenylpropan-1-one 
• 7391-29-9 2-methyl-3-oxo-3-phenylpropanenitrile 
• 14236-72-7 2-methylsulfanyl-1-phenyl-propan-1-one 
• 35016-08-1 7-methyl-6-phenyl-1,7-dihydro-pyrimido[4,5-b][1,4]thiazine-2,4-dione 
• 35016-09-2 1,3,7-trimethyl-6-phenyl-1,7-dihydro-pyrimido[4,5-b][1,4]thiazine-2,4-dione 
• 2042-85-5 1,2-diphenylpropan-1-one 
• 63017-05-0 2-bromo-2-chloropropiophenone 
• 21120-36-5 1-fluoroethyl phenyl ketone 
• 35553-88-9 2-Acetyl-1-benzoyl-1-methyl-cyclopropan 
• 24242-66-8 2-(4-methoxyphenoxy)-1-phenylpropan-1-one 
• 24264-50-4 2-(3,5-Dimethoxy-phenoxy)-1-phenyl-propan-1-on 
• 95280-23-2 α-(4-Acetyl-phenoxy)-propiophenon 
• 135186-09-3 2-methyl-1-phenylcyclopropanol 

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