2345-34-8

Basic information

• Product Name: 4-Acetoxybenzoic acid
• Synonyms: RARECHEM AL BE 0082;P-ACETOXYBENZOIC ACID;4-(Acetyloxy)benzoic acid;4-(acetyloxy)-benzoicaci;4-(Acetyloxy)benzoicacid;4-Acetate-benzoic acid;Benzoic acid, p-hydroxy-, acetate;O-Acetyl-p-hydroxybenzoic acid
• CAS NO: 2345-34-8
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• EINECS: 219-066-9
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic Acids (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Aldehydes;C9;Carbonyl Compounds
• Mol File: 2345-34-8.mol
• Article Data: 117

Chemical Properties

• Melting Point: 190-194 °C(lit.)
• Boiling Point: 272.96°C (rough estimate)
• Flash Point: 133.208 °C
• Appearance: white crystalline powder
• Density: 1.2933 (rough estimate)
• Vapor Pressure: 9.22E-05mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: almost transparency in Methanol
• PKA: pK1: 4.38 (25°C)
• BRN: 1871997
• CAS DataBase Reference: 4-Acetoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Acetoxybenzoic acid(2345-34-8)
• EPA Substance Registry System: 4-Acetoxybenzoic acid(2345-34-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 2345-34-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

4-Acetoxybenzoic acid has been used in the preparation of poly(4-hydroxybenzoate).

Definition

ChEBI: 4-acetoxy benzoic acid is a member of the class of benzoic acids that is benzoic acid substituted by an acetoxy group at position 4. It is a member of benzoic acids and a member of phenyl acetates.

General Description

Kinetics of the bulk polymerization of 4-acetoxybenzoic acid has been investigated. Mono and submono layers of 4-acetoxybenzoic acid chemisorbed on oxidized aluminum has been studied by IR-absorption spectroscopy.

InChI:InChI=1/C9H8O4/c1-6(10)13-8-4-2-7(3-5-8)9(11)12/h2-5H,1H3,(H,11,12)/p-1

Synthetic route

acetic anhydride (108-24-7) + 4-hydroxy-benzoic acid (99-96-7) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With pyridine In tetrahydrofuran; toluene at 0 - 20℃; for 16h;	100%
With Sulfate; titanium(IV) oxide In cyclohexane at 81℃; for 0.166667h;	98%
With lanthanum(III) nitrate at 20℃; for 0.333333h;	97%

methyl 4-acetoxybenzoate (24262-66-6) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With iodine; aluminium In acetonitrile at 80℃; for 18h;	99%

acetyl chloride (75-36-5) + 4-hydroxy-benzoic acid (99-96-7) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With pyridine In tetrahydrofuran for 1h; Cooling with ice;	98.6%
In cyclohexane at 30 - 40℃; for 2h; Concentration;	97%
In pyridine at 0 - 20℃; for 1.58333h;	82.3%

4-formylphenyl acetate (878-00-2) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With dihydrogen peroxide at 20℃; for 0.5h;	94%
With oxygen; C34H4F60NiO4 In toluene at 64℃; under 760 Torr; for 12h;	74%
With oxygen; acetic anhydride; butyraldehyde; cobalt(II) chloride In acetonitrile Ambient temperature;	62%
In water at 25℃; Rate constant; xanthine oxidase; also in aerosol OT/isooctane system;

acetic anhydride (108-24-7) + 4-hydroxy-benzaldehyde (123-08-0) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With oxygen; CoCl2 In 1,2-dichloro-ethane at 25℃;	93%
With oxygen; cobalt(II) chloride In 1,2-dichloro-ethane at 25℃; for 20h;	93%

methyl 4-acetoxybenzoate (24262-66-6) → 4-acetyloxy-benzoic acid (2345-34-8) + methyl 4-hydroxylbenzoate (99-76-3)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; 2-amino-benzenethiol at 100℃; for 0.75h; Hydrolysis;	A 7% B 93%

p-cresol (106-44-5) → 4-acetyloxy-benzoic acid (2345-34-8) + 1-acetoxy-4-methylbenzene (140-39-6)

Conditions	Yield
With acetic acid	A 92% B n/a

4-acetoxy-benzoic acid 3-methyl-but-2-enyl ester → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 5.5h;	89%

4-O-acetylbenzaldehyde oxime (757965-23-4) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With [hydroxy(tosyloxy)iodo]benzene; water In dimethyl sulfoxide at 20℃; for 24h;	89%

p-acetoxystyrene (2628-16-2) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 19h;	88%
With tert.-butylhydroperoxide In water at 50℃; for 12h; Sealed tube; Green chemistry;	80%
With Oxone; mesoporous silicate MCM-48 - osmium In N,N-dimethyl-formamide at 25℃; for 3h;	75%
With ammonium thiocyanate; oxygen In acetic acid at 25℃; for 8h;	30%

4-acetoxybenzyl alcohol (6309-46-2) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With oxygen In water; tert-butyl alcohol at 120℃; under 52505.3 Torr; for 0.533333h; Flow reactor; Green chemistry;	84%

C25H26O4Si → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With water; N,N-dimethyl-formamide at 45℃; for 12h; Green chemistry; chemoselective reaction;	84%

1-acetoxy-4-methylbenzene (140-39-6) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With zinc(II) oxide In N,N-dimethyl-formamide for 0.133333h; microwave irradiation;	83%
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate; acetic acid at 100℃; for 15h;	83%
With cerium(III) chloride; 1,1,1-trichloroethanol; oxygen In acetonitrile at 60℃; Irradiation;	80%

cobalt (II) acetate·4 H2O + manganese (II) acetate·4 H2O + 1-acetoxy-4-methylbenzene (140-39-6) + azobisisobutyronitrile (34241-39-9) + 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione (143435-52-3) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With acetic acid	82%

4-acetyloxyacetophenone (13031-43-1) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate In acetic acid at 100℃; under 760.051 Torr; for 15h;	74%
With hydrogen bromide; acetic anhydride; acetic acid In titanium-clad
With hydrogen bromide; acetic anhydride; acetic acid In titanium-clad
With cobalt(II) nitrate hexahydrate; manganese (II) nitrate tetrahydrate; oxygen at 100℃; for 8h;

1-acetoxy-4-methylbenzene (140-39-6) + manganese(II) acetate (638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3) → 4-acetyloxy-benzoic acid (2345-34-8) + acetyloxy(4-acetyloxyphenyl)methyl acetate (7143-16-0) + 4-(acetyloxy)benzyl acetate (2937-64-6)

Conditions	Yield
With sulfuric acid; ozone; potassium bromide at 5℃; under 760.051 Torr;	A n/a B 70% C 18%

acetic acid (64-19-7) + 4-hydroxy-benzoic acid (99-96-7) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With sodium hydroxide for 1h; cooling;	63%

4-(oxiran-2-yl)phenyl acetate (86952-89-8) → 4-acetyloxy-benzoic acid (2345-34-8) + 4-(1,2-dihydroxyethyl)phenyl acetate (439584-65-3) + 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
With oxygen; bismuth mandelate In dimethyl sulfoxide at 80℃; under 760 Torr; for 4.3h;	A 4% B 17% C 61%

4-acetoxycinnamic acid amide → 4-acetyloxy-benzoic acid (2345-34-8) + 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
Stage #1: 4-acetoxycinnamic acid amide With oxygen; ozone; acetic acid In water at 0 - 10℃; for 2h; Stage #2: With dihydrogen peroxide In water at 15 - 90℃; for 2h;	A 59% B 36%

3-(4-acetoxyphenyl)acrylic acid (27542-85-4, 50363-92-3, 15486-19-8) → 4-acetyloxy-benzoic acid (2345-34-8) + 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
Stage #1: 3-(4-acetoxyphenyl)acrylic acid With oxygen; ozone; acetic acid In water at 0 - 10℃; for 1.16667h; Stage #2: With dihydrogen peroxide In water at 15 - 95℃; for 3h;	A 51% B 30%

1-acetoxy-4-methylbenzene (140-39-6) + acetic anhydride (108-24-7) → 4-acetyloxy-benzoic acid (2345-34-8) + 4-(acetyloxy)benzyl acetate (2937-64-6)

Conditions	Yield
With ozone at 5℃; Kinetics;	A 9.2% B 7.8%

4-formylphenyl acetate (878-00-2) + tert-butylhypochlorite (507-40-4) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With tetrachloromethane

acetic anhydride (108-24-7) + benzene (71-43-2) + 4-hydroxy-benzoic acid (99-96-7) → 4-acetyloxy-benzoic acid (2345-34-8)

4-acetyl-benzoic acid (586-89-0) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With dihydrogen peroxide; trifluoroacetic anhydride In chloroform

4-nitrophenol acetate (830-03-5) + 4-hydroxy-benzoic acid (99-96-7) → 4-acetyloxy-benzoic acid (2345-34-8) + p-nitrophenolate (14609-74-6)

Conditions	Yield
With borate buffer; azoniacyclophane CP66 In 1,4-dioxane at 25℃; Rate constant;

p-cresol (106-44-5) + acetic anhydride (108-24-7) → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With acetic acid; sodium bromide; cobalt(II) acetate; manganese(II) acetate 1.) 110 deg C, 60 min, 2.) 105 deg C;

4.5-isopropylidene-(-)-quinid-<4-acetoxy benzoate> → 4-acetyloxy-benzoic acid (2345-34-8) + 7-(4-hydroxy-benzoyloxy)-2,2-dimethyl-tetrahydro-4,7-methano-[1,3]dioxolo[4,5-c]oxepin-6-one

Conditions	Yield
With sodium hydroxide at 18℃;

4-hydroxy-benzoic acid (99-96-7) + acetyl derivative → 4-acetyloxy-benzoic acid (2345-34-8)

acetic anhydride (108-24-7) + disodium-salt of/the/ 4-hydroxy-benzoic acid → 4-acetyloxy-benzoic acid (2345-34-8)

Conditions	Yield
With pyridine
With sodium hydroxide at 0℃;

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 oxalyl dichloride In dichloromethane at 20℃; for 6h;	100%

4-acetyloxy-benzoic acid (2345-34-8) → 4-hydroxy-benzoic acid (99-96-7)

Conditions	Yield
Stage #1: 4-acetyloxy-benzoic acid With sodium hydroxide; water at 90℃; for 15h; Stage #2: With hydrogenchloride In water	100%
With aluminum oxide In neat (no solvent) at 75℃; for 0.05h; microwave irradiation;	84%
With bismuth mandelate In dimethyl sulfoxide at 95℃; for 24h;	73%

ethanol (64-17-5) + 4-acetyloxy-benzoic acid (2345-34-8) → ethyl 4-acetoxybenzoate (13031-45-3)

Conditions	Yield
With magnesium chloride at 40℃; for 18h;	95%

4-acetyloxy-benzoic acid (2345-34-8) + 2-chloro-4-[(1r,3r)-3-amino-2,2,4,4-tetramethylcyclobutoxy]benzonitrile → 4-[[(1,3-trans)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl]phenyl acetate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h;	94%

4-acetyloxy-benzoic acid (2345-34-8) + 4-((1R,3R)-3-amino-2,2,4,4-tetramethylcyclobutoxy)-2-chlorobenzonitrile hydrogen chloride → 4-[[(1,3-trans)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl]phenyl acetate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;	94%

4-acetyloxy-benzoic acid (2345-34-8) + 6-[4-(4-aminophenyl)piperazin-1-yl]pyridine-3-carbonitrile → [4-[[4-[4-(5-cyano-2-pyridyl)piperazin-1-yl]phenyl]carbamoyl]phenyl] acetate

Conditions	Yield
Stage #1: 4-acetyloxy-benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20 - 25℃; for 1.5h; Stage #2: 6-[4-(4-aminophenyl)piperazin-1-yl]pyridine-3-carbonitrile With N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 25℃; for 0.5h;	92%

4-acetyloxy-benzoic acid (2345-34-8) + potassium thioacyanate (333-20-0) → 4-(isothiocyanatocarbonyl)phenyl acetate

Conditions	Yield
Stage #1: 4-acetyloxy-benzoic acid With trichloroisocyanuric acid; triphenylphosphine In toluene at 0℃; for 0.25h; Stage #2: potassium thioacyanate In toluene at 0 - 20℃; for 1.5h;	90%

4-acetyloxy-benzoic acid (2345-34-8) + diisopropylamine (108-18-9) → 4-hydroxy-N,N-bis(1-methylethyl)benzamide (79119-46-3)

Conditions	Yield
Stage #1: 4-acetyloxy-benzoic acid With thionyl chloride at 80℃; for 1h; Stage #2: diisopropylamine With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling;	89%

4-acetyloxy-benzoic acid (2345-34-8) + ethyl iodide (75-03-6) → ethyl 4-acetoxybenzoate (13031-45-3)

Conditions	Yield
With cesium fluoride In acetonitrile for 2h; Heating;	88%

piperidine (110-89-4) + 4-acetyloxy-benzoic acid (2345-34-8) → Acetic acid 4-(piperidine-1-carbonyl)-phenyl ester (60397-69-5)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane	88%

4-acetyloxy-benzoic acid (2345-34-8) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → 4-(4-acetoxy-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (681482-85-9)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane	88%

4-acetyloxy-benzoic acid (2345-34-8) + isosorbide mononitrate (16106-20-0, 16908-90-0, 16908-91-1, 35993-37-4, 38709-03-4, 114718-64-8, 127001-76-7, 16051-77-7) → (1S,4S,5R,8R)-8-nitrooxy-2,6-dioxabicyclo[3.3.0]octan-4-yl-4-acetoxybenzoate

Conditions	Yield
With dimethylallyl diphosphate; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 5h;	87%

4-acetyloxy-benzoic acid (2345-34-8) + (S)-1-((S)-2-Amino-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid (3,3,3-trifluoro-2-hydroxy-1-isopropyl-propyl)-amide → Acetic acid 4-{(S)-2-methyl-1-[(S)-2-(3,3,3-trifluoro-2-hydroxy-1-isopropyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-propylcarbamoyl}-phenyl ester (190388-19-3)

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 18h; Ambient temperature;	86%

(R)-2-pentanol (31087-44-2) + 4-acetyloxy-benzoic acid (2345-34-8) + benzylamine (100-46-9) → 4-hydroxy-1-(1-methylbutyloxycarbonyl)benzene

Conditions	Yield
With pyridine; thionyl chloride In toluene	86%

4-acetyloxy-benzoic acid (2345-34-8) + o-hydroxyacetophenone (118-93-4) → C17H14O5

Conditions	Yield
With pyridine; trichlorophosphate at 20℃; for 24h;	85%

4-acetyloxy-benzoic acid (2345-34-8) + 2-(2-pyridinyldisulfanyl)ethanamine hydrochloride → [4-[2-(2-pyridyldisulfanyl)ethylcarbamoyl]phenyl] acetate

Conditions	Yield
Stage #1: 4-acetyloxy-benzoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In dichloromethane at 20℃; for 0.166667h; Stage #2: 2-(2-pyridinyldisulfanyl)ethanamine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	84%

4-acetyloxy-benzoic acid (2345-34-8) + C15H29N3O5 → 4-(2,3-bis(tert-butoxycarbonyl)guanidino)butyl 4-acetoxybenzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	84%

Upstream product

• 75-36-5 acetyl chloride 
• 99-96-7 4-hydroxy-benzoic acid 
• 24262-66-6 methyl 4-acetoxybenzoate 
• 2628-16-2 p-acetoxystyrene 
• 33527-94-5 4-acetoxyiodobenzene 
• 144-62-7 oxalic acid 
• 108-24-7 acetic anhydride 
• 71-43-2 benzene 
• 878-00-2 4-formylphenyl acetate 
• 507-40-4 tert-butylhypochlorite 
• 127-08-2 potassium acetate 
• 757965-23-4 4-O-acetylbenzaldehyde oxime 
• 27542-85-4 3-(4-acetoxyphenyl)acrylic acid 
• 7400-08-0 para-coumaric acid 

Downstream Products

• 121575-87-9 bis-[4-(4-acetoxy-benzoyloxy)-phenyl]-sulfone 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 16357-40-7 3-acetyl-4-hydroxybenzoic acid 
• 98-89-5 Cyclohexanecarboxylic acid 
• 46437-76-7 4-acetoxy-benzoic acid vinyl ester 
• 114273-37-9 2-formyl-cis-bicyclo<3.3.0>octa-2,7-dien-exo-4-yl 4-acetoxybenzoate 
• 64-19-7 acetic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 24262-66-6 methyl 4-acetoxybenzoate 
• 736910-19-3 Acetic acid 4-(4-propyl-piperazine-1-carbonyl)-phenyl ester 
• 122504-06-7 C₂₁H₂₂O₆ 
• 386750-31-8 cholesteryl 4-(4-acetoxybenzoyloxy)-benzoate 
• 522658-84-0 5-(4-hydroxybenzoyl)pyrimidine-2,4,6-trione 
• 522658-83-9 5-(4-hydroxybenzoyl)-1,3-dimethylpyrimidine-2,4,6-trione 

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