27914-73-4

Basic information

• Product Name: 4-Acetoxy-benzoylchloride
• Synonyms: 4-Acetoxy-benzoylchloride;Benzoyl chloride, 4-(acetyloxy)-
• CAS NO: 27914-73-4
• Molecular Formula: C₉H₇ClO₃
• Molecular Weight: 198.61
• Mol File: 27914-73-4.mol
• Article Data: 114

Chemical Properties

• Melting Point: 28-31°C
• Boiling Point: 286.642 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.294 g/cm³
• CAS DataBase Reference: 4-Acetoxy-benzoylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Acetoxy-benzoylchloride(27914-73-4)
• EPA Substance Registry System: 4-Acetoxy-benzoylchloride(27914-73-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 27914-73-4(Hazardous Substances Data)

Usage

General Description

4-Acetoxy-benzoylchloride, also known as Benzoyl chloride, 4'-(acetyloxy), is a chemical compound with the formula C10H7ClO3. It is used in the production of various polymers, pharmaceuticals, and dyes. Due to its reactive nature, it is often used as an acylating agent in chemical synthesis. It appears as a light yellow to brown liquid, has a strong odor, and it's sensitive to moisture. Handling of 4-Acetoxy-benzoylchloride should be done with caution as it may cause burns to the skin, eyes, and mucous membranes. It is also combustible and poses a danger to the environment.

Synthetic route

4-acetyloxy-benzoic acid (2345-34-8) → 4-acetoxybenzoyl chloride (27914-73-4)

Conditions	Yield
With oxalyl dichloride at 20℃; for 4h;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h;	100%
With thionyl chloride at 79℃; for 4h; Heating / reflux;	99%

C11H25NO2Si (748122-53-4) + 3-(chlorocarbonyl)phenyl acetate (16446-73-4) → 4-acetoxybenzoyl chloride (27914-73-4)

Conditions	Yield
In dichloromethane 1.) 0 deg C, 30 min, 2.) RT, 1 h;

4-hydroxy-benzoic acid (99-96-7) → 4-acetoxybenzoyl chloride (27914-73-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / aq. NaOH / 1 h / cooling 2: thionyl chloride; N,N-dimethylformamide / 5 h / 70 °C View Scheme
With thionyl chloride; sulfuric acid In acetic anhydride
Multi-step reaction with 2 steps 1: 6 h / Reflux 2: thionyl chloride / 2 h / Reflux View Scheme

oxalyl dichloride (79-37-8) + 4-acetyloxy-benzoic acid (2345-34-8) → 4-acetoxybenzoyl chloride (27914-73-4)

4-acetyloxy-benzoic acid (2345-34-8) + N-cyclohexyl-cyclohexanamine (101-83-7) → 4-acetoxybenzoyl chloride (27914-73-4)

Conditions	Yield
With thionyl chloride In dichloromethane

methyl 4-acetoxybenzoate (24262-66-6) → 4-acetoxybenzoyl chloride (27914-73-4)

Conditions	Yield
With thionyl chloride In chloroform; N,N-dimethyl-formamide Reflux;

tert-butyl 4-hydroxybenzoate (25804-49-3) → 4-acetoxybenzoyl chloride (27914-73-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 16.25 h / 0 - 20 °C / Inert atmosphere 2: thionyl chloride; water / 16 h / 23 °C / Sealed tube View Scheme

tert-butyl 4-acetoxybenzoate (59854-09-0) → 4-acetoxybenzoyl chloride (27914-73-4)

Conditions	Yield
With thionyl chloride; water at 23℃; for 16h; Sealed tube;

4-acetoxybenzoyl chloride (27914-73-4) + 1'-[(3S)-3-(3,4-dichlorophenyl)-4-(methylamino)butyl]-N,N-dimethyl-1,4'-bipiperidine-4'-carboxamide trihydrochloride → 4-({[(2S)-2-(3,4-dichlorophenyl)-4-{4'-[(-N,N-dimethylamino)-carbonyl]1,4'-bipiperidin-1'-yl}butyl](methyl)amino}carbonyl)phenyl acetate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 15h;	100%

4-acetoxybenzoyl chloride (27914-73-4) + R-(-)-4-ethylhexan-2-ol (220150-55-0) → (R)-4-acetoxy-1-(3-ethyl-1-methylpentyloxycarbonyl)benzene (443682-67-5)

Conditions	Yield
With pyridine In dichloromethane; water	100%
With pyridine In toluene at 20℃; for 15h;	97%
With pyridine In water; toluene	92%
With pyridine In water; toluene	63 g (0.215 mol. yield 97%)

4-acetoxybenzoyl chloride (27914-73-4) + (R)-2-nonanol (628-99-9, 70419-06-6, 74683-66-2, 70419-07-7) → (R)-1-methyloctyl-4-acetoxyphenylcarboxylate (479629-72-6)

Conditions	Yield
With pyridine In dichloromethane; water	100%

4-acetoxybenzoyl chloride (27914-73-4) + 1'-[(3S)-3-(3,4-dichlorophenyl)-4-(methylamino)butyl]-N,N-dimethyl-1,4'-bipiperidine-4'-carboxamide hydrochloride → 4-({[(2S)-2-(3,4-dichlorophenyl)-4-{4'-[(-N,N-dimethylamino)-carbonyl]1,4'-bipiperidin-1'-yl}butyl](methyl)amino}carbonyl)phenyl acetate

Conditions	Yield
Stage #1: 4-acetoxybenzoyl chloride; 1'-[(3S)-3-(3,4-dichlorophenyl)-4-(methylamino)butyl]-N,N-dimethyl-1,4'-bipiperidine-4'-carboxamide hydrochloride With triethylamine In dichloromethane at 20℃; for 15h; Stage #2: With potassium hydroxide In tert-butyl methyl ether; water; ethyl acetate	100%

4-acetoxybenzoyl chloride (27914-73-4) + N,N-diethyl-2-(piperazin-1-yl)acetamide (40004-14-6) → Acetic acid 4-(4-diethylcarbamoylmethyl-piperazine-1-carbonyl)-phenyl ester; hydrochloride

Conditions	Yield
In diethyl ether at -15 - -10℃; for 0.166667h;	98%

4-acetoxybenzoyl chloride (27914-73-4) + methyl 2-amino-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (119004-72-7) → methyl 2-(4-hydroxybenzamido)-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Conditions	Yield
Stage #1: 4-acetoxybenzoyl chloride; methyl 2-amino-6-phenyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Stage #2: With lithium hydroxide monohydrate In tetrahydrofuran; methanol at 40℃; for 0.5h;	98%

1-(1-methylethyl)piperazine (4318-42-7) + 4-acetoxybenzoyl chloride (27914-73-4) → Acetic acid 4-(4-isopropyl-piperazine-1-carbonyl)-phenyl ester; hydrochloride

Conditions	Yield
In diethyl ether at -15 - -10℃; for 0.166667h;	97%

1-(2-(diethylamino)ethyl)piperazine (4038-92-0) + 4-acetoxybenzoyl chloride (27914-73-4) → Acetic acid 4-[4-(2-diethylamino-ethyl)-piperazine-1-carbonyl]-phenyl ester; hydrochloride

Conditions	Yield
In diethyl ether at -15 - -10℃; for 0.166667h;	97%

4-acetoxybenzoyl chloride (27914-73-4) + 1-n-propylpiperazine (21867-64-1) → Acetic acid 4-(4-propyl-piperazine-1-carbonyl)-phenyl ester; hydrochloride

Conditions	Yield
In diethyl ether at -15 - -10℃; for 0.166667h;	97%

4-acetoxybenzoyl chloride (27914-73-4) + 4-fluoropyridin-2-amine (944401-77-8) → 4-[(4-fluoropyridin-2-yl)carbamoyl]phenyl acetate

Conditions	Yield
In pyridine; dichloromethane at 20℃;	97%

4-acetoxybenzoyl chloride (27914-73-4) + butyl-iodo-manganese (62485-87-4) → Acetic acid 4-pentanoyl-phenyl ester (97037-82-6)

Conditions	Yield
In diethyl ether for 2h; Ambient temperature;	96%

4-acetoxybenzoyl chloride (27914-73-4) + 1-phenylmethylpiperazine (2759-28-6) → Acetic acid 4-(4-benzyl-piperazine-1-carbonyl)-phenyl ester; hydrochloride

Conditions	Yield
In diethyl ether at -15 - -10℃; for 0.166667h;	96%

4-acetoxybenzoyl chloride (27914-73-4) + benzene (71-43-2) → 4-acetoxybenzophenone (13031-44-2)

Conditions	Yield
With aluminium trichloride Friedels-Crafts benzoylation; Heating;	95%

4-acetoxybenzoyl chloride (27914-73-4) + N-trimethylsilylmethylamine (18166-02-4) → 4-{[(trimethylsilyl)methyl]carbamoyl}phenyl acetate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	94%

4-acetoxybenzoyl chloride (27914-73-4) + 2-amino-6-(1,1-dimethylethyl)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid methyl ester (213192-26-8) → methyl 2-(4-acetoxybenzamido)-6-(tert-butyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	93%

4-acetoxybenzoyl chloride (27914-73-4) + R-(-)-4-ethylhexan-2-ol (220150-55-0) → (R)-3-ethyl-1-methylpentyl-4-acetoxybenzoate

Conditions	Yield
With pyridine In toluene at 20℃; for 3h;	92%

4-acetoxybenzoyl chloride (27914-73-4) + isopropylamine (75-31-0) → 4-(isopropylcarbamoyl)phenyl acetate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; Schlenk technique;	92%

4-acetoxybenzoyl chloride (27914-73-4) + N-(3,5-dimethoxyphenyl)-N-methylamine (118684-17-6) → 4-{[(3,5-dimethoxyphenyl)(methyl)amino]carbonyl}phenyl acetate (1132660-78-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 1h;	91%

4-acetoxybenzoyl chloride (27914-73-4) + 3-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzohydrazide (1169389-62-1) → 4-(2-(3-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzoyl)hydrazinecarbonyl)phenyl acetate (1169389-79-0)

Conditions	Yield
Stage #1: 4-acetoxybenzoyl chloride; 3-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzohydrazide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18h; Stage #2: With pyridine In tetrahydrofuran; N,N-dimethyl-formamide for 1h;	90.9%

4-acetoxybenzoyl chloride (27914-73-4) + hydroquinone (123-31-9) → 1,4-bis(4-acetoxybenzoyloxy)-benzene (79066-38-9)

Conditions	Yield
With pyridine In 1,2-dichloro-ethane at 20℃; for 48h; Inert atmosphere;	90%

4-acetoxybenzoyl chloride (27914-73-4) + O-benzylhydoxylamine hydrochloride (2687-43-6) → 4-((benzyloxy)carbamoyl)phenyl acetate

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 1h;	90%

4-acetoxybenzoyl chloride (27914-73-4) + 4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzoylhydrazine (1169389-56-3) → 4-(2-(4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzoyl)hydrazinecarbonyl)phenyl acetate (1169389-75-6)

Conditions	Yield
Stage #1: 4-acetoxybenzoyl chloride; 4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzoylhydrazine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 19h; Stage #2: With pyridine In tetrahydrofuran; N,N-dimethyl-formamide for 1.5h;	90%

4-acetoxybenzoyl chloride (27914-73-4) + o-(methylamino)acetophenone (1859-75-2) → 4-{[(2-acetylphenyl)(methyl)amino]carbonyl}phenyl acetate (1319210-04-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; for 3h;	90%

4-acetoxybenzoyl chloride (27914-73-4) + chloro-p-hydroquinone (615-67-8) → C24H17ClO8

Conditions	Yield
With pyridine In 1,2-dichloro-ethane at 20℃; for 48h; Inert atmosphere;	90%
With pyridine In 1,2-dichloro-ethane

4-acetoxybenzoyl chloride (27914-73-4) + 2,3-O-isopropylidene-D-ribofuranose (67814-68-0, 70266-87-4, 76249-50-8, 76249-51-9, 93451-15-1, 4099-88-1) → C17H20O8

Conditions	Yield
With pyridine at 20℃; for 0.5h;	90%

4-acetoxybenzoyl chloride (27914-73-4) + 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethyl cyclohexane (129188-99-4) → (3,3,5-trimethylcyclohexane-1,1-diyl)bis(1,4-phenylene)bis(4-acetoxybenzoate)

Conditions	Yield
With pyridine at 110℃;	89%

4-acetoxybenzoyl chloride (27914-73-4) + 1,1-bis(4-hydroxyphenyl)cyclohexane (843-55-0) → 4-(1-{4-[(4-acetoxybenzoyl)oxy]phenyl}cyclohexyl)phenyl 4-acetoxybenzoate

Conditions	Yield
With pyridine at 110℃; Reflux;	89%
With pyridine at 110℃;	89%

4-acetoxybenzoyl chloride (27914-73-4) + thiosemicarbazide (79-19-6) → 4-(2-thiocarbamoylhydrazinocarbonyl) phenyl acetate (7001-76-5)

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h;	89%

4-acetoxybenzoyl chloride (27914-73-4) + 4-methyl-2-(piperazin-1-yl)quinoline (50693-78-2) → 4-methyl-2-(4-(4-acetoxybenzoyl)-1-piperazinyl)-quinoline

Conditions	Yield
Stage #1: 4-methyl-2-(piperazin-1-yl)quinoline With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: 4-acetoxybenzoyl chloride In dichloromethane at 20℃; for 0.25h;	88%

Upstream product

• 748122-53-4 C₁₁H₂₅NO₂Si 
• 16446-73-4 3-(chlorocarbonyl)phenyl acetate 
• 99-96-7 4-hydroxy-benzoic acid 
• 79-37-8 oxalyl dichloride 
• 2345-34-8 4-acetyloxy-benzoic acid 
• 59854-09-0 tert-butyl 4-acetoxybenzoate 
• 25804-49-3 tert-butyl 4-hydroxybenzoate 
• 24262-66-6 methyl 4-acetoxybenzoate 
• 101-83-7 N-cyclohexyl-cyclohexanamine 

Downstream Products

• 79119-31-6 N, N-diethyl-4-hydroxybenzamide 
• 87539-80-8 Acetic acid 4-(6-chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-phenyl ester 
• 121867-26-3 4-(4-Acetoxy-benzoylamino)-benzoic acid ethyl ester 
• 180986-54-3 4-Acetoxy-benzoic acid 2-phenyl-propyl ester 
• 24262-65-5 phenyl 4-(acetyloxy)benzoate 
• 183591-54-0 4-acetoxybenzoyl-4-phenylpiperidine 
• 180136-44-1 4-acetoxy-N-(2-methyl-5-nitrophenyl)benzamide 
• 180136-46-3 N-(2-methoxy-5-nitrophenyl)-4-acetoxybenzamide 
• 207238-96-8 [6-(4-Acetoxy-benzoyl)-benzo[1,3]dioxol-5-yl]-acetic acid methyl ester 
• 212118-15-5 2'-(trimethylsilyl)ethyl-4-acetoxybenzoate 
• 386750-97-6 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-bis[(4-acetoxybenzoyl)oxy]calix[4]arene 
• 146922-83-0 ethyl 4-[1-(4-acetoxybenzoyl)indolizin-3-yl]butyrate 
• 259268-32-1 acetic acid 4-(4'-bromo-biphenyl-4-carbonyl)-phenyl ester 

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