6323-18-8

Basic information

• Product Name: 2-chloropropiophenone
• Synonyms: 1-(2-chlorophenyl)propan-1-one;1-Propanone,1-(2-chlorophenyl)-;NSC 32597
• CAS NO: 6323-18-8
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.62
• Mol File: 6323-18-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 115-116℃ (15 Torr)
• Appearance: /
• Density: 1.128±0.06 g/cm3(Predicted)
• Refractive Index: 1.5320 to 1.5360
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Benzene, Chloroform, DMSO, Methanol
• CAS DataBase Reference: 2-chloropropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloropropiophenone(6323-18-8)
• EPA Substance Registry System: 2-chloropropiophenone(6323-18-8)

Safety Data

• Hazardous Substances Data: 6323-18-8(Hazardous Substances Data)

Usage

General Description

2-Chloropropiophenone is a synthetic organic chemical compound characterized by a phenyl ring bonded to a propiophenone group with a chlorine atom attached. Its molecular formula is C9H9ClO, indicating it consists of 9 carbon, 9 hydrogen, one chlorine, and one oxygen atom. 2-chloropropiophenone falls into the chemical category of phenylpropanoids and polyketides. Its uses are mainly industrial, specifically in the pharmaceutical and chemical industries, as it is often utilized as a chemical intermediate in the production of other substances. Commonly, it is used in the synthesis of pharmaceuticals, such as antidepressants and antihistamines. It should be handled with care, as it may be harmful if swallowed, inhaled, or made contact with skin or eyes.

Synthetic route

2-chloro-α-ethylbenzyl alcohol (22869-35-8) → 2-chloropropiophenone (6323-18-8)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;	99%
With chromium(VI) oxide; sulfuric acid In acetone for 2h;
With chromium(VI) oxide; sulfuric acid In water; acetone at 10℃; Jones oxidation;

2-Chlorobenzonitrile (873-32-5) + ethylmagnesium bromide (925-90-6) → 2-chloropropiophenone (6323-18-8)

Conditions	Yield
Stage #1: 2-Chlorobenzonitrile; ethylmagnesium bromide Stage #2: With water Further stages.;	89%
Stage #1: 2-Chlorobenzonitrile; ethylmagnesium bromide Stage #2: With sulfuric acid	79%

2'-Aminopropiophenon (1196-28-7) → 2-chloropropiophenone (6323-18-8)

Conditions	Yield
With hydrogenchloride; copper(l) chloride at 70℃;

ethylmagnesium iodide (10467-10-4) + 2-Chlorobenzonitrile (873-32-5) → 2-chloropropiophenone (6323-18-8)

Conditions	Yield
(i), (ii) aq. H2SO4; Multistep reaction;

methyl-malonic acid dimethylester (609-02-9) + o-chlorobenzoyl chloride (609-65-4) → 2-chloropropiophenone (6323-18-8)

Conditions	Yield
(i) Mg, I2, EtOH, CCl4, benzene, (ii) /BRN= 386435/; Multistep reaction;

2-chloro-benzaldehyde (89-98-5) → 2-chloropropiophenone (6323-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.33 h / -78 - 20 °C 1.2: 65 percent / 4 h / 20 °C 2.1: 99 percent / PCC / CH2Cl2 / 2 h / 20 °C View Scheme

2-chloro-benzaldehyde (89-98-5) + (+-)-piperoin → 2-chloropropiophenone (6323-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: CrO3; H2SO4 / acetone; H2O / 10 °C View Scheme

2-Chlorobenzonitrile (873-32-5) → 2-chloropropiophenone (6323-18-8) + 2-bromo-2'-chloropropiophenone (75815-22-4)

sesquiethylaluminum chloride dimer + o-chlorobenzoyl chloride (609-65-4) → 2-chloropropiophenone (6323-18-8)

Conditions	Yield
With aluminium trichloride at 40℃;

methanol (67-56-1) + 2-chloropropiophenone (6323-18-8) → 1-(2-chlorophenyl)-2-methyl-propan-1-one (5408-59-3)

Conditions	Yield
With C34H27IrN2P(1+)*C32H12BF24(1-); caesium carbonate at 65℃; for 24h; Inert atmosphere;	89%

2-chloropropiophenone (6323-18-8) → 2-chloro-α-ethylbenzyl alcohol (22869-35-8)

Conditions	Yield
With dimethylsulfide borane complex In diethyl ether for 24h; Heating; further reducing agents;	85%

2-chloropropiophenone (6323-18-8) + dibenzylamine (103-49-1) → (E)-1-(2-chlorophenyl)-2-methyl-3-phenylprop-2-en-1-one

Conditions	Yield
With ammonium peroxydisulfate In tert-Amyl alcohol Inert atmosphere;	79%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + 2-chloropropiophenone (6323-18-8) + trimethylphosphane (594-09-2) → Ni(C6H4-o-C(O)CH2CH3)(Cl)(PMe3)2 (897400-48-5)

Conditions	Yield
In toluene under N2 atm. soln. PMe3 in toluene was added to suspn. Ni(cod)2 in toluene at -78°C, allowed to warm to room temp., 2-chloropropiophenone was added and stirred at 45°C for 4 h; solvent was evapd. in vacuo, residue was extd. with Et2O, concd. and cooled to -20°C; elem. anal.;	75%

methyl selenide (6486-05-1) + 2-chloropropiophenone (6323-18-8) → 2-Methylselenopropiophenon (6512-85-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	68%

2-chloropropiophenone (6323-18-8) + diethylazodicarboxylate (1972-28-7) → C15H19ClN2O5 (1469875-61-3) + C15H19ClN2O5

Conditions	Yield
With trifluorormethanesulfonic acid; N-(1S,2S)-2-[(R)-3,5-dihydro-4H-dinaphth[2,1-c:10,20-e]azepin-4-yl]cyclohexanamine In isopropyl alcohol at 20℃; for 96h; Molecular sieve; enantioselective reaction;	A 65% B n/a

formaldehyd (50-00-0) + 2-chloropropiophenone (6323-18-8) + pyrrolidine hydrochloride (25150-61-2) → 1-(2-Chloro-phenyl)-2-methyl-3-pyrrolidin-1-yl-propan-1-one

Conditions	Yield
With hydrogenchloride In isopropyl alcohol Heating;	62%

2-chloropropiophenone (6323-18-8) → (S)-1-(2-chlorophenyl)propanol (158635-38-2)

Conditions	Yield
With Rhizopus arrhizus In ethanol at 20℃; for 192h;	62%

piperidine (110-89-4) + 2-chloropropiophenone (6323-18-8) → 2-piperidin-1-[(3-(chlorophenyl))]propan-1-one

Conditions	Yield
With ammonium iodide In acetonitrile at 20℃; Electrolysis;	60%

2-hydroxy-2-methylpropionohydrazide (42596-46-3) + 2-chloropropiophenone (6323-18-8) → 2-Hydroxy-2-methyl-propionic acid [1-(2-chloro-phenyl)-prop-(E)-ylidene]-hydrazide (122433-05-0)

Conditions	Yield
In ethanol for 4h;	58%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + 2-chloropropiophenone (6323-18-8) + Dimethyl(phenyl)phosphine (672-66-2) → Ni(C6H4-o-C(O)CH2CH3)(Cl)(PMe2Ph)2 (897400-50-9)

Conditions	Yield
In toluene under N2 atm. PMe2Ph was added to suspn. Ni(cod)2 in toluene at -78°C, allowed to warm to room temp., 2-chloropropiophenone was added andstirred at 45°C for 4 h; solvent was evapd. in vacuo, residue was extd. with THF, cooled to -20°C; elem. anal.;	58%

2-chloropropiophenone (6323-18-8) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 2-chloropiophenone 4-methylphenylsulfonylhydrazone (767288-70-0) + 2-chloropiophenone 4-methylphenylsulfonylhydrazone

Conditions	Yield
With acetyl chloride In ethanol for 25h; Heating;	A 49% B 21%

2-chloropropiophenone (6323-18-8) + Diphenylphosphine oxide (4559-70-0) → 1-(2-chlorophenyl)-2-(diphenylphosphoryl)propan-1-one

Conditions	Yield
With copper(l) iodide; t-butyldimethylsiyl triflate; oxygen; triethylamine In acetonitrile at 20℃; for 2h;	32%

2-chloropropiophenone (6323-18-8) → 2-chlorophenylacetone (6305-95-9)

Conditions	Yield
Multistep reaction;

2-chloropropiophenone (6323-18-8) → 1-(o-Chlorophenyl)-2,2-dichloro-1-propanone (35996-45-3)

Conditions	Yield
With sodium acetate; chlorine In acetic acid
With chlorine

2-chloropropiophenone (6323-18-8) → 1-(o-chlorophenyl)-2-chloro-1-propanone (81671-55-8)

Conditions	Yield
With hydrogenchloride; chlorine 1.) CH2Cl2, 0 deg C, 1 h, 2.) RT, overnight; Yield given. Multistep reaction;

2-chloropropiophenone (6323-18-8) → (R)-1-(2-chlorophenyl)propanol + (S)-1-(2-chlorophenyl)propanol (158635-38-2)

Conditions	Yield
With chiral (R,R)-<(R)-styrene oxide/benzylamine/samarium(III)>; isopropyl alcohol Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; tetrabutylammomium bromide; water; sodium formate; (2S)-pyrrolidine-2-carboxylic acid N-((1R)-1-phenyl-ethyl)-amide at 40℃; for 24h; optical yield given as %ee; enantioselective reaction;

2-chloropropiophenone (6323-18-8) → 1-(o-Chlorophenyl)-2,2-dibromo-1-propanone (69086-88-0)

Conditions	Yield
With bromine

2-chloropropiophenone (6323-18-8) → 2-bromo-2'-chloropropiophenone (75815-22-4)

Conditions	Yield
With bromine In tetrachloromethane
With bromine In dichloromethane; water at 35℃;
With bromine; acetic acid In diethyl ether at 0 - 20℃;

2-chloropropiophenone (6323-18-8) → 1-(2-chloro-phenyl)-propan-1-one oxime

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol at 20℃; for 18h;

2-chloropropiophenone (6323-18-8) + methoxycarbonylmethylamine (616-34-2) → [1-(2-chloro-phenyl)-propylamino]-acetic acid methyl ester

Conditions	Yield
With thiophene; hydrogen; palladium on activated charcoal In methanol

carbon monoxide (201230-82-2) + 2-chloropropiophenone (6323-18-8) → 3-(Z)-(methylmethylene)-1(3H)-isobenzofuranone (4767-62-8)

Conditions	Yield
Stage #1: 2-chloropropiophenone With bis(1,5-cyclooctadiene)nickel (0) In toluene at 45℃; for 72h; Stage #2: With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Stage #3: carbon monoxide In tetrahydrofuran at 20℃; for 0.0833333h;

2-chloropropiophenone (6323-18-8) → 3-ethyl-1-(4-methylphenylsulfonyl)indazole

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / acetyl chloride / ethanol / 25 h / Heating 2: 43 percent / t-BuONa / Pd(OAc)2; dppp / dioxane / 15 h / 50 °C View Scheme

Upstream product

• 609-02-9 methyl-malonic acid dimethylester 
• 609-65-4 o-chlorobenzoyl chloride 
• 873-32-5 2-Chlorobenzonitrile 
• 925-90-6 ethylmagnesium bromide 
• 89-98-5 2-chloro-benzaldehyde 
• 10467-10-4 ethylmagnesium iodide 
• 22869-35-8 2-chloro-α-ethylbenzyl alcohol 
• 1196-28-7 2'-Aminopropiophenon 

Downstream Products

• 75815-22-4 2-bromo-2'-chloropropiophenone 
• 767288-70-0 2-chloropiophenone 4-methylphenylsulfonylhydrazone 
• 90919-30-5 1-o-Chlor-phenyl-1-methoxy-aceton 
• 5408-59-3 1-(2-chlorophenyl)-2-methyl-propan-1-one 
• 1469875-61-3 C₁₅H₁₉ClN₂O₅ 

Relevant articles and documents

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Syntheses of 3-substituted indazoles and benzoisoxazoles were efficiently accomplished with the aid of Pd-catalyzed intramolecular carbon-nitrogen and carbon-oxygen bond formations. The catalyst system described herein allows the cyclization to proceed under very mild conditions and thus could be applied to a wide range of substrates with acid- or base-sensitive functional groups. A total synthesis for the indazole ring-containing natural product nigellicine is also described.

Cyclic enolates of Ni and Pd: Equilibrium between C- and O-bound tautomers and reactivity studies

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