3874-54-2

Basic information

• Product Name: 4-Chloro-4'-fluorobutyrophenone
• Synonyms: 3-CHLOROPROPYL4-FLUOROPHENYLKETONE/4-CHLORO-4''-FLUOROBUTYROPHENONE;1-Butanone, 4-chloro-1-(4-fluorophenyl)-;1-(4-Fluorophenyl)-4-chloro-1-butanone;γ-Chloro-4'-fluorobutyrophenone;ω-Chloro-4'-fluorobutyrophenone;4-Chloro-4'-fluorobu;4-chloro-4-fluorophenyl ketone;1-Chloro-4-(4-fluorophenyl)-4-oxobutane
• CAS NO: 3874-54-2
• Molecular Formula: C₁₀H₁₀ClFO
• Molecular Weight: 200.64
• EINECS: 223-395-3
• Product Categories: ketone;Fluorobenzene;C10;Carbonyl Compounds;Ketones;Aromatics;Miscellaneous Reagents;API Intermediate
• Mol File: 3874-54-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 5-6 °C
• Boiling Point: 130-132 °C (0.97513 mmHg)
• Flash Point: >230 °F
• Appearance: Slightly yellow-greenish clear/Oil
• Density: 1.22 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5255(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility: 0.38 g/L (20 ºC)
• BRN: 608741
• CAS DataBase Reference: 4-Chloro-4'-fluorobutyrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-4'-fluorobutyrophenone(3874-54-2)
• EPA Substance Registry System: 4-Chloro-4'-fluorobutyrophenone(3874-54-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3874-54-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3874-54-2 differently. You can refer to the following data:
1. 4-Chloro-4'-fluorobutyrophenone (cas# 3874-54-2) is a compound useful in organic synthesis.
2. 4-Chloro-4''-fluorobutyrophenone (cas# 3874-54-2) is a compound useful in organic synthesis.

Chemical Properties

slightly yellow-greenish clear oil

Synthetic route

fluorobenzene (462-06-6) + 4-Chlorobutanoyl chloride (4635-59-0) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; for 4h; Time;	90%
With aluminium trichloride In carbon disulfide at 20℃; for 2h;	73.2%
With aluminium trichloride

4-chloro-1-(4-fluorophenyl)-1,1-(ethylenedioxy)butane (3308-94-9) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
In(OSO2CF3)3 In acetone at 100℃; for 0.0833333h; microwave irradiation;	89%

4-flourophenylmagnesium bromide (352-13-6) + 4-Chlorobutanoyl chloride (4635-59-0) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
Stage #1: 4-Chlorobutanoyl chloride With 1-methyl-pyrrolidin-2-one In toluene at 0℃; for 0.5h; Stage #2: 4-flourophenylmagnesium bromide In tetrahydrofuran; toluene at -10 - 0℃; for 4.25h; chemoselective reaction;	88%

1-(4-chlorobut-1-yn-1-yl)-4-fluorobenzene (1183278-95-6) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With iron(III) chloride; water; silver(I) triflimide In 1,4-dioxane for 18h; regioselective reaction;	85%
With water; bis(trifluoromethanesulfonyl)amide In 1,4-dioxane at 100℃;	85%
With water In 1,4-dioxane at 80 - 120℃; regioselective reaction;	85%

1-(4-fluorophenyl)cyclobutan-1-ol (339365-53-6) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With manganese(II) triflate; tetrabutylammonium acetate; acetic acid; magnesium chloride In acetonitrile at 25℃; for 3.5h; Inert atmosphere; Electrochemical reaction; Sealed tube;	84%
With 1,10-Phenanthroline; tert-butylhypochlorite; silver trifluoromethanesulfonate In acetonitrile at 20℃; for 6h; Inert atmosphere; Schlenk technique; regioselective reaction;	81%

4-chlorobutyraldehyde (6139-84-0) + 1-Bromo-4-fluorobenzene (460-00-4) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With Quinuclidine; 4,4'-di-tert-butyl-2,2'-bipyridine nickel(II) bromide; [Ir(C6H2F2-C5H3NCF3)2(4,4′-di-tert-butyl-2,2′-dipyridyl)]; potassium carbonate In 1,4-dioxane at 20℃; for 20h; Inert atmosphere; Sealed tube; Irradiation;	77%
With palladium diacetate; 9,10-phenanthrenequinone; potassium hydrogencarbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In acetone at 20℃; for 24h; Reagent/catalyst; Irradiation;	71%

1-iodo-3-chloro-propane (6940-76-7) + 4-fluoroboronic acid (1765-93-1) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
Stage #1: 1-iodo-3-chloro-propane; 4-fluoroboronic acid With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; benzene at 20℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Irradiation; Stage #2: molybdenum hexacarbonyl With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 70℃; Suzuki-Miyaura Coupling; Inert atmosphere;	68%

1-ethynyl-4-fluorobenzene (766-98-3) + 3-chloropropionyl peroxide (19263-25-3) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; trifluorormethanesulfonic acid In tetrahydrofuran at 70 - 80℃; for 12.25h; Inert atmosphere; Schlenk technique;	60%

3-chloro-4'-fluoropropiophenone (347-93-3) + diethyl 4-chloromethyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate (3613-34-1) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
With manganese; di-tert-butyl peroxide; α,α,α-trifluorotoluene at 100℃; for 48h; Inert atmosphere;	51%

1-Bromo-4-fluorobenzene (460-00-4) → 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / Inert atmosphere; Reflux; Sealed tube 1.2: 0 - 20 °C / Inert atmosphere; Sealed tube 2.1: acetic acid; manganese(II) triflate; magnesium chloride; tetrabutylammonium acetate / acetonitrile / 3.5 h / 25 °C / Inert atmosphere; Electrochemical reaction; Sealed tube View Scheme

para-thiocresol (106-45-6) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-fluorophenyl)-4-(p-tolylthio)butan-1-one (132427-90-8)

Conditions	Yield
	100%
With triethylamine In tetrahydrofuran for 16h; Ambient temperature;	99%

N-methoxylamine hydrochloride (593-56-6) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 4-chloro-1-(4-fluorophenyl)butan-1-one O-methyl oxime (1352950-38-9)

Conditions	Yield
With pyridine at 20℃;	100%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → cyclopropyl(4-fluorophenyl)methanone (772-31-6)

Conditions	Yield
With sodium hydroxide In water at 60℃; for 5h;	100%

toluene-3-thiol (108-40-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(Fluorophenyl)-4-(3-methylphenylthio)-1-butanone

Conditions	Yield
With triethylamine In tetrahydrofuran	99%
With triethylamine In tetrahydrofuran	99%

toluene-3-thiol (108-40-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-Fluorophenyl)-4-(3-methylphenylthio)-1-butanone

Conditions	Yield
With triethylamine In tetrahydrofuran	99%

ethylene glycol (107-21-1) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 4-chloro-1-(4-fluorophenyl)-1,1-(ethylenedioxy)butane (3308-94-9)

Conditions	Yield
With toluene-4-sulfonic acid In water; toluene for 16h; Inert atmosphere; Reflux;	98%
With toluene-4-sulfonic acid In benzene for 18h; Heating;	93%
With toluene-4-sulfonic acid In benzene for 15h; Heating;	90%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + 1-(2,5-dimethylphenyl)piperazine (1013-25-8) → 4-[4-(2,5-dimethylphenyl)piperazin-1-yl]-1-(4-fluorophenyl)butan-1-one

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In acetonitrile for 22h; Reflux;	96%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → (+/-)-4-chloro-1-(4-fluorophenyl)butan-1-ol (51787-87-2)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0℃; for 7h;	95%
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 3h;	94%
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 12h;	93%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-iodo-3-(p-fluorophenylcarbonyl)propane (40862-32-6)

Conditions	Yield
With sodium iodide In butanone for 3h; Heating;	95%
With sodium iodide In acetone for 24h; Reflux;	92%
With sodium iodide In acetone for 16h; Reflux;	77%
In sodium iodide; butanone
With sodium iodide In [(2)H6]acetone for 8h; Reflux;

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 4-(n-butyl)fluorobenzene (20651-65-4)

Conditions	Yield
With nickel In tetrahydrofuran for 15h; Heating;	95%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → C10H10FN3O (154440-76-3)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide	95%
With sodium azide; potassium iodide In N,N-dimethyl-formamide at 90℃;

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (S,E)-N-(4-chloro-1-(4-fluorophenyl)butylidene)-2-methylpropane-2-sulfinamide (1218989-31-1)

Conditions	Yield
With titanium (IV) ethoxide In tetrahydrofuran at 65℃; for 48h; Inert atmosphere;	94%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → C10H11FO

Conditions	Yield
Stage #1: 4-(4-fluorophenyl)-4-oxo-n-butyl chloride With C32H33FeN3O2Si; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at -40 - 20℃; for 2h; Schlenk technique; Glovebox; Stage #2: With potassium carbonate In methanol; toluene at 20℃; for 12h; Schlenk technique; Glovebox; enantioselective reaction;	94%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + 1-Phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (1021-25-6) → spiperone (749-02-0)

Conditions	Yield
With diisopropylamine In N,N-dimethyl-formamide at 80℃; for 17h; Inert atmosphere;	93%
With triethylamine; potassium iodide In acetonitrile for 20h; Heating;	74%
With triethylamine; potassium iodide In acetonitrile for 20h; Inert atmosphere; Reflux;	63%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + potassium thioacetate (10387-40-3) → S-(4-(4-fluorophenyl)-4-oxobutyl) ethanethioate

Conditions	Yield
In N,N-dimethyl-formamide at 0 - 20℃; for 10h; Inert atmosphere;	92%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → (1R)-(+)-4-chloro-1-(4-fluorophenyl)butan-1-ol (126640-11-7)

Conditions	Yield
With B-chlorodiisopinocampheylborane In diethyl ether at -25℃; for 16h;	90%
With C22H27Cl2CoN3O; sodium triethylborohydride; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; enantioselective reaction;	87%
Stage #1: 4-(4-fluorophenyl)-4-oxo-n-butyl chloride With Triethoxysilane; (S,E)-(+)-2,6-diisopropyl-N-(2-((2-(4-phenyl-4,5-dihydrooxazol-2-yl)phenyl)amino)benzylidene)aniline; sodium triethylborohydride; cobalt(II) chloride In tetrahydrofuran; dichloromethane at 20℃; for 15h; Schlenk technique; Inert atmosphere; Stage #2: With potassium carbonate In tetrahydrofuran; methanol; dichloromethane at 20℃; for 2h; Schlenk technique; Inert atmosphere; enantioselective reaction;	75%
Multi-step reaction with 2 steps 1: 81 percent / NaBH4 / methanol / 4 °C View Scheme
With B-chlorodiisopinocampheylborane In tetrahydrofuran; diethyl ether; 2,2'-iminobis[ethanol] at 25℃;

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → (1S)-(-)-4-chloro-1-(4-fluorophenyl)butan-1-ol (126640-10-6)

Conditions	Yield
With (-)-diisopinocamphenylborane chloride In diethyl ether at -25℃; for 16h;	90%
Multi-step reaction with 2 steps 1: 81 percent / NaBH4 / methanol / 4 °C View Scheme
With (-)-diisopinocamphenylborane chloride In tetrahydrofuran; diethyl ether; 2,2'-iminobis[ethanol] at 25℃;

4-fluorobenzylic alcohol (459-56-3) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → cyclopropyl-[4-(4-fluoro-benzyloxy)-phenyl]-methanone (868699-44-9)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran at 30℃; for 18h;	90%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → (-)-4-chloro-1-(4-fluorophenyl)butan-1-ol

Conditions	Yield
Stage #1: 4-(4-fluorophenyl)-4-oxo-n-butyl chloride With (S)-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine; phenylsilane; copper(II) acetate monohydrate In toluene at -20 - 20℃; for 48h; Stage #2: With hydrogenchloride In water; toluene Reagent/catalyst; enantioselective reaction;	90%

fluoroiodomethane (373-53-5) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 5-chloro-1-fluoro-2-(4-fluorophenyl)pentan-2-ol

Conditions	Yield
With methyllithium lithium bromide In tetrahydrofuran; diethyl ether at -78℃; for 0.0833333h; Inert atmosphere;	90%

1-phenylmethylpiperazine (2759-28-6) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → cyclopropyl-{4-(4-benzylpiperazin-1-yl)phenyl}methanone

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 140℃;	90%

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-chlorobutyl)-4-fluorobenzene (54540-58-8)

Conditions	Yield
With triethylsilane; trifluoroacetic acid at 0℃; for 2h;	89%
With hydrogen; palladium on activated charcoal In ethanol
With hydrogenchloride; mercury dichloride; zinc In toluene for 5h; Reflux;
With triethylsilane In trifluoroacetic acid

4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) + 4-flourophenylmagnesium bromide (352-13-6) → δ-Hydroxy-δ-bis(p-fluorophenyl)butyl chloride (51787-80-5)

Conditions	Yield
In diethyl ether Heating;	88.4%

4-hydroxy-4-phenylpiperidin (40807-61-2) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 1-(4-fluorophenyl)-4-(4-hydroxy-4-phenylpiperidin-1-yl)butan-1-one (3109-12-4)

Conditions	Yield
With sodium hydrogencarbonate; potassium iodide In toluene for 24h; Reflux;	88%
With potassium iodate; potassium carbonate In toluene Inert atmosphere;	27%
With toluene; potassium iodide

4-(4-chlorophenyl)-4-hydroxypiperidine (39512-49-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → haloperidol (52-86-8)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 75℃; for 24h; Temperature;	88%
With potassium iodide In toluene for 45h; Reflux;	85%
With potassium iodide In toluene at 130℃; for 45h; Sealed tube;	79%

1-(4-chlorophenyl)-1,4-diazepane (41885-98-7) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → 4-(4-(4-chlorophenyl)-1,4-diazepan-1-yl)-1-(4-fluorophenyl)butan-1-one

Conditions	Yield
With potassium carbonate; potassium iodide In 1,2-dimethoxyethane for 18h; Heating;	87%

[bis(acetoxy)iodo]benzene (3240-34-4) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2) → C12H12ClFO3 (1394244-16-6)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In 1,4-dioxane at 20℃; for 1h;	87%

Upstream product

• 347-93-3 3-chloro-4'-fluoropropiophenone 
• 3613-34-1 diethyl 4-chloromethyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 6139-84-0 4-chlorobutyraldehyde 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 19263-25-3 3-chloropropionyl peroxide 
• 6940-76-7 1-iodo-3-chloro-propane 
• 1765-93-1 4-fluoroboronic acid 
• 13939-06-5 molybdenum hexacarbonyl 
• 339365-53-6 1-(4-fluorophenyl)cyclobutan-1-ol 
• 1183278-95-6 1-(4-chlorobut-1-yn-1-yl)-4-fluorobenzene 
• 352-13-6 4-flourophenylmagnesium bromide 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 3308-94-9 4-chloro-1-(4-fluorophenyl)-1,1-(ethylenedioxy)butane 

Downstream Products

• 21492-58-0 4-(2,3-dihydro-5H-benzo[f][1,4]oxazepin-4-yl)-1-(4-fluoro-phenyl)-butan-1-one 
• 104271-43-4 5,6-dihydro-8-<4-(1H-imidazol-1-yl)phenyl>imidazo<1,2-a>pyridine 
• 35623-04-2 4-Benzyl-1-[4-(4-fluorophenyl)-4-oxo-1-butyl]piperidine 
• 125834-97-1 9-γ-(4-fluorobenzoyl)propyl-9-azabicyclo<3.3.1>nonan-3-one 
• 170921-52-5 8-[4-(4-fluoro-phenyl)-4-oxo-butyl]-1,3,8-triaza-spiro[4.5]decan-4-one 
• 38077-13-3 4-(p-Chloro-α-hydroxybenzyl)-1-[3-(p-fluorobenzoyl)propyl]piperidine 
• 36116-18-4 cyclopropyl 4-hydroxyphenyl ketone 
• 841200-22-4 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dithiane 
• 868699-45-0 cyclopropyl-[4-(furan-2-ylmethoxy)-phenyl]-methanone 
• 184025-18-1 ciproxifan 
• 1050-79-9 moperone 

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