CAS No.501-92-8,4-ALLYLPHENOL Suppliers

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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: 501-92-8 MF: C9H10O MW: 134.18 Appeara

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Synthetic route

: 140-67-0
Estragole

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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%

: 106-48-9
4-chloro-phenol

: 762-72-1
allyl-trimethyl-silane

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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%

: 95081-49-5
4-[3-(2-Nitro-phenylselanyl)-propyl]-phenol

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 3698-32-6
p-ethoxyallylbenzene

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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%

: 540-38-5
4-Iodophenol

: 106-95-6
allyl bromide

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 106-48-9
4-chloro-phenol

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 106-48-9
4-chloro-phenol

: 762-72-1
allyl-trimethyl-silane

A: 501-92-8
4-(prop-2-enyl)phenol

B: 108-95-2
phenol

Conditions

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

...Expand

: 4873-09-0
allyl tosylate

: 108-95-2
phenol

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 140-67-0
Estragole

A: 501-92-8
4-(prop-2-enyl)phenol

B: 4-(2-bromopropyl)phenol

Conditions

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%

: 1415236-88-2
2-(4-(allyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 1516-28-5
allyl (p-tolyl)sulfide

: 89713-14-4, 932-97-8
4-diazo-2,5-cyclohexadienone

A: 501-92-8
4-(prop-2-enyl)phenol

B: 2-allyl-4-(p-tolylthio)phenol

Conditions

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%

...Expand

: 1746-13-0
allyl phenyl ether

A: 501-92-8
4-(prop-2-enyl)phenol

B: 1745-81-9
2-Allylphenol

C: 108-95-2
phenol

Conditions

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;

...Expand

: C15H18O5

: C15H18O5

B: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 107-18-6
allyl alcohol

: 108-95-2
phenol

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 140-67-0
Estragole

: 917-64-6
methyl magnesium iodide

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

Conditions	Yield
at 160 - 170℃;

: 94-59-7
1-allyl-3,4-methylenedioxybenzene

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

Conditions	Yield
With ethanol; ammonia; sodium

: 32704-23-7
4-(2-propenyl)aniline

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

Conditions	Yield
With sulfuric acid; sodium nitrite anschliessendes Erwaermen;

: (4-allyl-phenyl)-magnesium bromide

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

Conditions	Yield
With diethyl ether; oxygen

: 1746-13-0
allyl phenyl ether

: 67-63-0
isopropyl alcohol

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

Conditions	Yield
Irradiation.UV-Licht;

: 1746-13-0
allyl phenyl ether

: 67-63-0
isopropyl alcohol

A: 501-92-8
4-(prop-2-enyl)phenol

B: 108-95-2
phenol

Conditions

Conditions	Yield
UV-Licht.Irradiation;

...Expand

: 106-95-6
allyl bromide

: 108-95-2
phenol

A: 501-92-8
4-(prop-2-enyl)phenol

B: 20490-18-0
2,4-di(prop-2-en-1-yl)phenol

C: 1745-81-9
2-Allylphenol

Conditions

Conditions	Yield
With sodium hydroxide In water

...Expand

: 218618-79-2
(2-Allyl-phenoxy)-trimethyl-silan

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

Conditions	Yield
With acid In methanol Yield given;

: 67-56-1
methanol

: 108-24-7
acetic anhydride

: 66648-51-9
miyaginin

A: 501-92-8
4-(prop-2-enyl)phenol

B: 20880-54-0
methyl 2,3,4-tri-O-acetyl-α-D-xylopyranoside

C: 604-70-6
Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester

Conditions

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

...Expand

: 83864-82-8
dimethylovobatol

A: 501-92-8
4-(prop-2-enyl)phenol

B: 5888-52-8
4-propyl-1,2-dimethoxybenzene

Conditions

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

A: 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
2,3,4-tri-O-methyl-D-glucopyranose

B: 501-92-8
4-(prop-2-enyl)phenol

C: 2,3-di-O-methyl-D-apiose

Conditions

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

...Expand

: 70482-71-2
1-allyl-4-(methoxymethoxy)benzene

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 140-67-0
Estragole

: 74-96-4
ethyl bromide

: 71-43-2
benzene

magnesium: magnesium

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

...Expand

: 106-41-2
4-bromo-phenol

isobutyl halide: isobutyl halide

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 25458-45-1
p-methoxymethoxybromobenzene

: 501-92-8
4-(prop-2-enyl)phenol

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 18162-48-6
tert-butyldimethylsilyl chloride

: (4-allylphenoxy)(tert-butyl)dimethylsilane

Conditions

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%

: 501-92-8
4-(prop-2-enyl)phenol

: 115-11-7
isobutene

: 339531-14-5
1-(tert-butoxy)-4-(prop-2-enyl)benzene

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 100-39-0
benzyl bromide

: 90617-59-7
1-(benzyloxy)-4-(prop-2-en-1-yl)benzene

Conditions

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

: 22065-57-2
ethyl 2-phenyldiazoacetate

: 501-92-8
4-(prop-2-enyl)phenol

: ethyl 2-(4-allylphenoxy)-2-phenylacetate

Conditions

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%

: 501-92-8
4-(prop-2-enyl)phenol

: 107-30-2
chloromethyl methyl ether

: 70482-71-2
1-allyl-4-(methoxymethoxy)benzene

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 108-24-7
acetic anhydride

: 61499-22-7
phenol, 4-(2-propenyl)-, acetate

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: (E)-4,4'-(but-2-ene-1,4-diyl)diphenol

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 123-08-0
4-hydroxy-benzaldehyde

Conditions

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

: 1515-78-2
buta-1,3-dien-1-ylbenzene

: 501-92-8
4-(prop-2-enyl)phenol

: (E)-4-allyl-2-(4-phenylbut-3-en-2-yl)phenol

Conditions

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

: 1515-78-2
buta-1,3-dien-1-ylbenzene

: 501-92-8
4-(prop-2-enyl)phenol

: 4-allyl-2-(4-phenylbut-3-en-2-yl)phenol

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 6746-81-2, 118712-54-2, 70987-78-9
(S)-Glycidyl tosylate

: 1176891-21-6
(S)-2-((4-allylphenoxy)methyl)oxirane

Conditions

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%

: 501-92-8
4-(prop-2-enyl)phenol

: 88-10-8
N,N-diethylcarbamyl chloride

: 1213270-14-4
C14H19NO2

Conditions

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%

: 501-92-8
4-(prop-2-enyl)phenol

: 79-30-1
isobutyryl chloride

: 1365640-10-3
4-allylphenyl isobutyrate

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 528-43-8
Magnolol

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 108-12-3
isopentanoyl chloride

: 1365640-11-4
4-allylphenyl 3-methylbutanoate

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 79-03-8
propionyl chloride

: 1365640-09-0
4-allylphenyl propionate

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 98-88-4
benzoyl chloride

: 4204-49-3
4-allylphenyl benzoate

Conditions

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

: 358-23-6
trifluoromethylsulfonic anhydride

: 501-92-8
4-(prop-2-enyl)phenol

: trifluoro-methanesulfonic acid 4-allyl-phenyl ester

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 459-57-4
4-fluorobenzaldehyde

: 1616458-13-9
4-(4-allyl phenoxy)benzaldehyde

Conditions

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

: 501-92-8
4-(prop-2-enyl)phenol

: 4-allyl-2,6-dibromophenol

Conditions

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%

: 31110-30-2
(Z)-but-2-enamide

: 501-92-8
4-(prop-2-enyl)phenol

: (Z)-4-(4-hydroxyphenyl)but-2-enamide

Conditions

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%

: 3240-34-4
[bis(acetoxy)iodo]benzene

: 501-92-8
4-(prop-2-enyl)phenol

: 108886-90-4
1-allyl-4-oxocyclohexa-2,5-dienylethanoate

Conditions

Conditions	Yield
In acetic acid for 8h;	60%

: 501-92-8
4-(prop-2-enyl)phenol

: 92758-75-3
benzyl (Z)-but-2-enoate

: benzyl (Z)-4-(4-hydroxyphenyl)but-2-enoate

Conditions

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%

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