501-92-8

Basic information

• Product Name: 4-ALLYLPHENOL
• Synonyms: 4-(2-propenyl)-pheno;4-(Prop-2-enyl)-phenol;Chavicol;gamma-(p-Hydroxyphenyl)-alpha-propylene;p-Allylphenol;p-Chavicol;Phenol, 4-(2-propenyl)-;Phenol, p-allyl-
• CAS NO: 501-92-8
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• EINECS: 207-929-2
• Mol File: 501-92-8.mol
• Article Data: 58

Chemical Properties

• Melting Point: 15.8°
• Boiling Point: bp760 238°; bp16 123°
• Flash Point: 102.6 °C
• Appearance: /
• Density: d415 1.0203; d420 1.0175
• Vapor Pressure: 0.0282mmHg at 25°C
• Refractive Index: nD18 1.5441
• PKA: 10.24±0.13(Predicted)
• CAS DataBase Reference: 4-ALLYLPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ALLYLPHENOL(501-92-8)
• EPA Substance Registry System: 4-ALLYLPHENOL(501-92-8)

Safety Data

• Hazardous Substances Data: 501-92-8(Hazardous Substances Data)

Usage

Description

4-Allylphenol, a phenylpropanoid, is a naturally occurring compound found in various plant sources such as Syzygium aromaticum leaves, Alpinia galanga oil, bay leaf oil, and betel leaf. It is characterized by its colorless liquid appearance and medicinal phenolic aroma with high strength odor. This organic compound is defined as a phenol substituted by a prop-2-enyl group at position 4 and has significant applications in different industries.

Uses

Used in Synthetic Chemistry:
4-Allylphenol is used as a building block in the synthetic, regioselective preparation of gamma-lactones, which are important intermediates in the synthesis of various biologically active compounds and pharmaceuticals.
Used in Flavor and Fragrance Industry:
4-Allylphenol is used as a flavoring agent and additive in the flavor and fragrance industry due to its high strength odor and phenolic type aroma. It is recommended to smell it in a 0.10% solution or less to appreciate its characteristic fragrance.
Used in Essential Oils:
4-Allylphenol is found in essential oils such as Alpinia galanga oil, bay leaf oil, and betel leaf, where it contributes to the overall aroma and therapeutic properties of these oils.

Synthetic route

Estragole (140-67-0) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;	100%
With boron tribromide In dichloromethane at 0℃; for 1h; Inert atmosphere;	97.5%
With dimethylsulfide; boron tribromide Heating;	95%

4-chloro-phenol (106-48-9) + allyl-trimethyl-silane (762-72-1) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With caesium carbonate In 2,2,2-trifluoroethanol for 14h; Irradiation;	87%
With caesium carbonate In 2,2,2-trifluoroethanol for 4h; Irradiation; Flow reactor;	70%

4-[3-(2-Nitro-phenylselanyl)-propyl]-phenol (95081-49-5) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With dihydrogen peroxide In tetrahydrofuran at 40℃; for 3.5h;	80%

p-ethoxyallylbenzene (3698-32-6) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
Stage #1: p-ethoxyallylbenzene With aluminum (III) chloride; N,N-dimethyl-aniline In toluene at 100 - 110℃; for 2 - 3h; Stage #2: With hydrogenchloride; water In toluene at 20℃; pH=1 - 2; Product distribution / selectivity;	80%

4-Iodophenol (540-38-5) + allyl bromide (106-95-6) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
Stage #1: p-Iodophenol With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at 40℃; for 2h; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 12h;	79%
Stage #1: p-Iodophenol With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at -78 - 40℃; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction;	79%

allylboronic acid N-methyl-iminodiacetic acid ester + 4-chloro-phenol (106-48-9) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With potassium carbonate In water at 135℃; for 0.3h; Suzuki-Miyaura Coupling; Microwave irradiation; Sealed tube;	75%

4-chloro-phenol (106-48-9) + allyl-trimethyl-silane (762-72-1) → 4-(prop-2-enyl)phenol (501-92-8) + phenol (108-95-2)

Conditions	Yield
In water; acetonitrile for 2.5h; Concentration; Irradiation; Flow reactor;	A 75% B 7 %Chromat.

allyl tosylate (4873-09-0) + phenol (108-95-2) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
{(norbornadiene)rhodium(I)(NCCH3)2}(PF6) In toluene at 0℃; for 24h;	54%

Estragole (140-67-0) → 4-(prop-2-enyl)phenol (501-92-8) + 4-(2-bromopropyl)phenol

Conditions	Yield
Stage #1: Estragole With boron tribromide In dichloromethane at 0 - 20℃; for 3.75h; Inert atmosphere; Stage #2: With water In dichloromethane Inert atmosphere;	A 49% B 31%

2-(4-(allyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1415236-88-2) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With C14H16N6; palladium diacetate; calcium hydroxide In N,N-dimethyl acetamide; water at 70℃; for 48h; Inert atmosphere;	43%

allyl (p-tolyl)sulfide (1516-28-5) + 4-diazo-2,5-cyclohexadienone (89713-14-4, 932-97-8) → 4-(prop-2-enyl)phenol (501-92-8) + 2-allyl-4-(p-tolylthio)phenol

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In 1,2-dichloro-ethane at 40℃; Inert atmosphere; Molecular sieve; Schlenk technique; chemoselective reaction;	A 41% B 32%

allyl phenyl ether (1746-13-0) → 4-(prop-2-enyl)phenol (501-92-8) + 2-Allylphenol (1745-81-9) + phenol (108-95-2)

Conditions	Yield
With β‐cyclodextrin In water at 25℃; for 0.5h; Irradiation;	A 21.9% B 40.2% C 2.1%
With β‐cyclodextrin In water at 25℃; for 0.5h; Quantum yield; Irradiation; without β-CD, in nitrogen or oxygen atmosphere;	A 21.9% B 40.2% C 2.1%
In methanol Product distribution; Kinetics; Quantum yield; Further Variations:; Solvents; Reagents; photo-Claisen rearrangement; Irradiation;
In butan-1-ol at 35℃; for 0.0833333h; Temperature; Time; Concentration; Claisen Rearrangement; Flow reactor; UV-irradiation;

C15H18O5 → C15H18O5 + 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 25℃;	A 38% B 8%

allyl alcohol (107-18-6) + phenol (108-95-2) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With KU-2-8 cation-exchange resin at 95 - 97℃; for 4h;	10%

Estragole (140-67-0) + methyl magnesium iodide (917-64-6) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
at 160 - 170℃;

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With ethanol; ammonia; sodium

4-(2-propenyl)aniline (32704-23-7) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With sulfuric acid; sodium nitrite anschliessendes Erwaermen;

(4-allyl-phenyl)-magnesium bromide → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With diethyl ether; oxygen

allyl phenyl ether (1746-13-0) + isopropyl alcohol (67-63-0) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
Irradiation.UV-Licht;

allyl phenyl ether (1746-13-0) + isopropyl alcohol (67-63-0) → 4-(prop-2-enyl)phenol (501-92-8) + phenol (108-95-2)

Conditions	Yield
UV-Licht.Irradiation;

allyl bromide (106-95-6) + phenol (108-95-2) → 4-(prop-2-enyl)phenol (501-92-8) + 2,4-di(prop-2-en-1-yl)phenol (20490-18-0) + 2-Allylphenol (1745-81-9)

Conditions	Yield
With sodium hydroxide In water

(2-Allyl-phenoxy)-trimethyl-silan (218618-79-2) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With acid In methanol Yield given;

methanol (67-56-1) + acetic anhydride (108-24-7) + miyaginin (66648-51-9) → 4-(prop-2-enyl)phenol (501-92-8) + methyl 2,3,4-tri-O-acetyl-α-D-xylopyranoside (20880-54-0) + Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester (604-70-6)

Conditions	Yield
With pyridine; sulfuric acid 1) reflux, 14 h, 2) room temperature, 14 h; Yield given. Multistep reaction. Yields of byproduct given;

dimethylovobatol (83864-82-8) → 4-(prop-2-enyl)phenol (501-92-8) + 4-propyl-1,2-dimethoxybenzene (5888-52-8)

Conditions	Yield
With potassium In ammonia at -70 - -62℃; for 1.5h;

{(3S,4R,5R)-5-[(2R,3R,4S,5R,6S)-6-(4-Allyl-phenoxy)-3,4,5-trimethoxy-tetrahydro-pyran-2-ylmethoxy]-3,4-dimethoxy-tetrahydro-furan-3-ylmethoxy}-tert-butyl-dimethyl-silane → 2,3,4-tri-O-methyl-D-glucopyranose (1136-20-5, 1136-21-6, 4239-62-7, 13704-10-4, 27539-49-7, 32568-58-4, 35775-21-4, 35775-22-5, 84413-48-9) + 4-(prop-2-enyl)phenol (501-92-8) + 2,3-di-O-methyl-D-apiose

Conditions	Yield
With hydrogenchloride In ethanol for 2h; Heating; Yield given;

1-allyl-4-(methoxymethoxy)benzene (70482-71-2) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
With sulfuric acid; acetic acid
With hydrogenchloride In tetrahydrofuran for 3h; Heating; Yield given;

Estragole (140-67-0) + ethyl bromide (74-96-4) + benzene (71-43-2) + magnesium → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
Erhitzen des Reaktionsprodukts bei 10-15 mm Druck auf 150-160grad;

4-bromo-phenol (106-41-2) + isobutyl halide → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / K2CO3 / acetone / 2 h / Heating 2: 1.) Mg / 1.) THF, 2.) THF, reflux, 3 h 3: 3N aq. HCl / tetrahydrofuran / 3 h / Heating View Scheme

p-methoxymethoxybromobenzene (25458-45-1) → 4-(prop-2-enyl)phenol (501-92-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Mg / 1.) THF, 2.) THF, reflux, 3 h 2: 3N aq. HCl / tetrahydrofuran / 3 h / Heating View Scheme

4-(prop-2-enyl)phenol (501-92-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (4-allylphenoxy)(tert-butyl)dimethylsilane

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 20℃; Inert atmosphere;	98%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;	96%

4-(prop-2-enyl)phenol (501-92-8) + isobutene (115-11-7) → 1-(tert-butoxy)-4-(prop-2-enyl)benzene (339531-14-5)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at -78℃; for 3h;	96%

4-(prop-2-enyl)phenol (501-92-8) + benzyl bromide (100-39-0) → 1-(benzyloxy)-4-(prop-2-en-1-yl)benzene (90617-59-7)

Conditions	Yield
With potassium carbonate In acetone for 4h; Reflux;	95%

ethyl 2-phenyldiazoacetate (22065-57-2) + 4-(prop-2-enyl)phenol (501-92-8) → ethyl 2-(4-allylphenoxy)-2-phenylacetate

Conditions	Yield
Stage #1: ethyl 2-phenyldiazoacetate; 4-(prop-2-enyl)phenol In 1,2-dichloro-ethane at 20℃; for 0.0333333h; Schlenk technique; Green chemistry; Stage #2: With trifluorormethanesulfonic acid In 1,2-dichloro-ethane for 0.333333h; Schlenk technique; Green chemistry;	90%
With sewage sludge-derived carbonaceous materials treated by perchloric acid; air In 1,2-dichloro-ethane at 20 - 70℃; under 750.075 Torr; for 5h; Schlenk technique;	72%

4-(prop-2-enyl)phenol (501-92-8) + chloromethyl methyl ether (107-30-2) → 1-allyl-4-(methoxymethoxy)benzene (70482-71-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran 1.) r.t., 1 h, 2.) r.t., 12 h;	89%

4-(prop-2-enyl)phenol (501-92-8) + acetic anhydride (108-24-7) → phenol, 4-(2-propenyl)-, acetate (61499-22-7)

Conditions	Yield
With pyridine at 20℃; for 16h;	89%
With dmap; triethylamine In dichloromethane at 20℃; for 0.333333h;	71%
With triethylamine In dichloromethane

4-(prop-2-enyl)phenol (501-92-8) → (E)-4,4'-(but-2-ene-1,4-diyl)diphenol

Conditions	Yield
With Grubbs catalyst first generation In dichloromethane for 4.5h; Inert atmosphere; Reflux;	87.3%

4-(prop-2-enyl)phenol (501-92-8) → 4-hydroxy-benzaldehyde (123-08-0)

Conditions	Yield
With iron(III) chloride; tetramethyldisiloxane In ethanol at 20℃; for 24h;	86%

buta-1,3-dien-1-ylbenzene (1515-78-2) + 4-(prop-2-enyl)phenol (501-92-8) → (E)-4-allyl-2-(4-phenylbut-3-en-2-yl)phenol

Conditions	Yield
With tris(pentafluorophenyl)borate In toluene at 25℃; for 0.5h; chemoselective reaction;	84%

buta-1,3-dien-1-ylbenzene (1515-78-2) + 4-(prop-2-enyl)phenol (501-92-8) → 4-allyl-2-(4-phenylbut-3-en-2-yl)phenol

Conditions	Yield
With tris(pentafluorophenyl)borate In toluene at 25℃; for 0.5h; Inert atmosphere; Sealed tube;	84%

4-(prop-2-enyl)phenol (501-92-8) + (S)-Glycidyl tosylate (6746-81-2, 118712-54-2, 70987-78-9) → (S)-2-((4-allylphenoxy)methyl)oxirane (1176891-21-6)

Conditions	Yield
Stage #1: 4-(prop-2-enyl)phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: (S)-Glycidyl tosylate In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	79%

4-(prop-2-enyl)phenol (501-92-8) + N,N-diethylcarbamyl chloride (88-10-8) → C14H19NO2 (1213270-14-4)

Conditions	Yield
With dmap In dichloromethane at 0 - 23℃; for 6h; Inert atmosphere;	78%
With dmap In dichloromethane at 0 - 23℃; for 6h; Inert atmosphere;	78%
With dmap In dichloromethane at 0 - 23℃; for 6h; Inert atmosphere;	78%

4-(prop-2-enyl)phenol (501-92-8) + isobutyryl chloride (79-30-1) → 4-allylphenyl isobutyrate (1365640-10-3)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	78%

4-(prop-2-enyl)phenol (501-92-8) → Magnolol (528-43-8)

Conditions	Yield
With aluminium trichloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In nitromethane for 1.5h; Ambient temperature;	77%
With air; ethanol; iron(III) chloride

4-(prop-2-enyl)phenol (501-92-8) + isopentanoyl chloride (108-12-3) → 4-allylphenyl 3-methylbutanoate (1365640-11-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	75%

4-(prop-2-enyl)phenol (501-92-8) + propionyl chloride (79-03-8) → 4-allylphenyl propionate (1365640-09-0)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	73%

4-(prop-2-enyl)phenol (501-92-8) + benzoyl chloride (98-88-4) → 4-allylphenyl benzoate (4204-49-3)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	70%
With sodium hydroxide
Stage #1: 4-(prop-2-enyl)phenol With sodium hydroxide In water Stage #2: benzoyl chloride In water for 0.5h;	0.32 g

trifluoromethylsulfonic anhydride (358-23-6) + 4-(prop-2-enyl)phenol (501-92-8) → trifluoro-methanesulfonic acid 4-allyl-phenyl ester

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	66%

4-(prop-2-enyl)phenol (501-92-8) + 4-fluorobenzaldehyde (459-57-4) → 4-(4-allyl phenoxy)benzaldehyde (1616458-13-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 48h;	63%

4-(prop-2-enyl)phenol (501-92-8) → 4-allyl-2,6-dibromophenol

Conditions	Yield
With N-Bromosuccinimide; tert-butylamine In dichloromethane at 0℃; for 1h;	61%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃; for 2.08333h;	50.6%

(Z)-but-2-enamide (31110-30-2) + 4-(prop-2-enyl)phenol (501-92-8) → (Z)-4-(4-hydroxyphenyl)but-2-enamide

Conditions	Yield
Stage #1: 4-(prop-2-enyl)phenol With (Z)-2-Butene; C33H28Cl2F2N2ORuS2 In tetrahydrofuran at 22℃; for 1h; Cross Metathesis; Inert atmosphere; Stage #2: (Z)-but-2-enamide In tetrahydrofuran at 22℃; for 20h; Cross Metathesis; Inert atmosphere; diastereoselective reaction;	61%

[bis(acetoxy)iodo]benzene (3240-34-4) + 4-(prop-2-enyl)phenol (501-92-8) → 1-allyl-4-oxocyclohexa-2,5-dienylethanoate (108886-90-4)

Conditions	Yield
In acetic acid for 8h;	60%

4-(prop-2-enyl)phenol (501-92-8) + benzyl (Z)-but-2-enoate (92758-75-3) → benzyl (Z)-4-(4-hydroxyphenyl)but-2-enoate

Conditions	Yield
Stage #1: 4-(prop-2-enyl)phenol With (Z)-2-Butene; C33H28Cl2F2N2ORuS2 In tetrahydrofuran at 22℃; for 1h; Cross Metathesis; Inert atmosphere; Stage #2: benzyl (Z)-but-2-enoate In tetrahydrofuran at 22℃; for 20h; Cross Metathesis; Inert atmosphere; diastereoselective reaction;	59%

Upstream product

• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 106-95-6 allyl bromide 
• 108-95-2 phenol 
• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 66648-51-9 miyaginin 
• 140-67-0 Estragole 
• 74-96-4 ethyl bromide 
• 71-43-2 benzene 
• 95605-38-2 1-(4-hydroxyphenyl)prop-2-en-1-one 
• 1516-28-5 allyl (p-tolyl)sulfide 
• 89713-14-4 4-diazo-2,5-cyclohexadienone 
• 106-48-9 4-chloro-phenol 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 3698-32-6 p-ethoxyallylbenzene 
• 70482-71-2 1-allyl-4-(methoxymethoxy)benzene 
• 59877-61-1 HO-NBA 
• 22805-47-6 3-(p-hydroxyphenyl)-1,2-propanediol 
• 540469-70-3 5-allyl-2-ethoxybenzylphosphine 
• 540469-71-4 bis(hydroxymethyl)(5-allyl-2-ethoxybenzyl)phosphine 
• 540469-74-7 1,5-di-p-tolyl-3,7-di(5'-allyl-2'-ethoxybenzyl)-1,5,3,7-diazadiphosphacyclooctane 
• 100-09-4 4-methoxybenzoic acid 
• 1209481-15-1 (E)-4-(1-propen-1-yl)phenyl propionate 
• 1365640-09-0 4-allylphenyl propionate 
• 13263-68-8 (E)-4-(1-propen-1-yl)phenyl 3-methylbutanoate 

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