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

Chemical Properties

Colorless liquid; medicinal phenolic aroma

Occurrence

Reported found in Alpinia galanga oil (0.20%), bay leaf oil (<0.01–15.51%), bay leaf oil anise (0.8%), bay leaf oil clove (17.1%), and betel leaf.

Uses

4-Allylphenol is a useful building block naturally occurring in Syzygium aromaticum leaves. 4-Allylphenol has been used in the synthetic, regioselective preparation of gamma-lactones.

Definition

ChEBI: A phenylpropanoid that is phenol substituted by a prop-2-enyl group at position 4.

Aroma threshold values

High strength odor; phenolic type; recommend smelling in a 0.10% solution or less

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

• 140-67-0 Estragole 
• 917-64-6 methyl magnesium iodide 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 74-96-4 ethyl bromide 
• 71-43-2 benzene 
• 106-48-9 4-chloro-phenol 
• 762-72-1 allyl-trimethyl-silane 
• 95605-38-2 1-(4-hydroxyphenyl)prop-2-en-1-one 
• 106-95-6 allyl bromide 
• 97-53-0 4-allylguaiacol 
• 269409-70-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 1415236-88-2 2-(4-(allyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 20649-40-5 (E)-4-(3-hydroxyprop-1-enyl)phenol 
• 3698-32-6 p-ethoxyallylbenzene 

Downstream Products

• 140-67-0 Estragole 
• 64704-00-3 p-allylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 93673-81-5 magnolignan A 
• 95058-15-4 p-allylphenyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside 
• 66648-51-9 miyaginin 
• 95058-14-3 miyaginin hexaacetate 
• 64703-98-6 4-hydroxy-allylbenzene 4-O-β-D-glucopyranoside 
• 100-09-4 4-methoxybenzoic acid 
• 528-43-8 Magnolol 
• 139726-29-7 dunnianol 
• 87688-90-2 isomagnolol 
• 82095-40-7 1--2,3-epoxypropan 
• 20649-40-5 (E)-4-(3-hydroxyprop-1-enyl)phenol 
• 108886-90-4 1-allyl-4-oxocyclohexa-2,5-dienylethanoate 

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