Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(II) chloride In diethyl ether for 12h; Heating; | 90% |
Conditions | Yield |
---|---|
With organo lithium reagent In hexane at 20℃; for 24h; | A 80% B 86% |
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; cobalt acetylacetonate In tetrahydrofuran at 15 - 20℃; for 0.25h; | 80% |
Conditions | Yield |
---|---|
With C68H72Cl2N6NiP2 In tetrahydrofuran at 50℃; for 12h; Inert atmosphere; | 77% |
1-propenylboronic acid
4-chloromethoxybenzene
anethole
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate In 1,4-dioxane for 24h; Suzuki-Miyaura cross-coupling; Heating; | 58% |
(E)-methyl 3-(3-bromo-4-hydroxyphenyl)acrylate
A
Estragole
B
trans-2-bromo-4-(3-hydroxypropen-1-yl)phenol
C
anethole
Conditions | Yield |
---|---|
With aluminium hydride In diethyl ether for 1h; Ambient temperature; Yields of byproduct given; | A n/a B 48% C n/a |
ethyl p-methoxycinnamate
A
Estragole
B
p-methoxycinnamyl alcohol
C
anethole
Conditions | Yield |
---|---|
With aluminium hydride In diethyl ether for 0.5h; Ambient temperature; Yields of byproduct given; | A n/a B 47% C n/a |
anethole
Conditions | Yield |
---|---|
Stage #1: carbonic acid 1-(4-methoxy-phenyl)-allyl ester methyl ester With bis(1,5-cyclooctadiene)diiridium(I) dichloride; dibenzyl ether; N-isopropylidene-N’-2-nitrobenzenesulfonyl hydrazine In acetonitrile for 18h; Sealed tube; Inert atmosphere; Glovebox; Stage #2: With acetic acid In tetrahydrofuran; 2,2,2-trifluoroethanol; water for 2h; Sealed tube; Inert atmosphere; Glovebox; regioselective reaction; | 45% |
Conditions | Yield |
---|---|
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 70℃; i = 250 mA, nickel-sponge cathode; | 44% |
Estragole
A
1-methoxy-4-(4-(p-methoxyphenyl)but-3-enyl)benzene
B
4,4'-dimethoxystilbene
C
1,3-bis(4-methoxyphenyl)prop-1-ene
D
anethole
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 40℃; Inert atmosphere; Schlenk technique; | A n/a B n/a C n/a D n/a E 41% |
Conditions | Yield |
---|---|
With trityl tetrafluoroborate In dichloromethane at -78℃; for 30h; | 15% |
Conditions | Yield |
---|---|
With infusorial earht at 500℃; | |
iridium(III) chloride; β‐cyclodextrin In water at 95℃; for 2.5h; | |
PEG-KOH In potassium hydroxide; toluene at 65℃; Mechanism; Rate constant; variations of stirring rate, aqueous KOH concentration, and catalyst (7-130 oxyethylene units / PEG monomethyl, dimethyl, and dibenzyl ethers), other temp.; activation energy; |
acetic anhydride
A
N,N-dimethyl acetamide
B
1-(4-methoxyphenyl)prop-1-yl acetate
C
anethole
Conditions | Yield |
---|---|
With sodium proprionate |
propene
(4-Methoxyphenyl)mercuric acetate
A
Estragole
B
1-isopropenyl-4-methoxybenzene
C
anethole
Conditions | Yield |
---|---|
(i) Pd(OAc)2, MeCN, (ii) /BRN= 1696878/; Multistep reaction; |
Conditions | Yield |
---|---|
With H2O2 or O2; copper dichloride; palladium dichloride In ethanol |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane Yield given; | |
Stage #1: ethyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at 20℃; for 12h; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 1h; | 52 % Chromat. |
A
1-isopropenyl-4-methoxybenzene
B
4-methoxyphenylcyclopropane
C
anethole
Conditions | Yield |
---|---|
at 160℃; Yield given. Yields of byproduct given; |
anethole
anethole
Conditions | Yield |
---|---|
With sulfuric acid durch Destillation; |
anethole
Conditions | Yield |
---|---|
With potassium carbonate | |
With pyridine |
anethole
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
at 500℃; |
1-(4-methoxyphenyl)prop-1-yl acetate
anethole
Conditions | Yield |
---|---|
With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen In toluene at 60℃; under 7500.75 Torr; for 24h; chemoselective reaction; | 99% |
With sodium hydrogen telluride In ethanol Heating; overnight; | 94% |
With formic acid; Pd(SIPr)(PCy3) In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With iodic acid; potassium bromide In dichloromethane; water at 20℃; for 0.166667h; | 99% |
With periodic acid; potassium bromide In dichloromethane; water at 20℃; for 0.133333h; | 98% |
With diethyl ether; bromine |
2-(2-phenylethynyl)-1,4-benzoquinone
anethole
2-(4-methoxyphenyl)-2-methyl-7-(phenylethynyl)-2,3-dihydrobenzofuran-5-ol
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 0℃; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
Stage #1: propionic acid With 2,6-dimethylpyridine; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; thiophenol In 1,2-dichloro-ethane at 0 - 23℃; for 0.25h; Inert atmosphere; Stage #2: anethole In 1,2-dichloro-ethane for 30h; Inert atmosphere; Irradiation; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
Stage #1: isobutyric Acid With 2,6-dimethylpyridine; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; thiophenol In 1,2-dichloro-ethane at 0 - 23℃; for 0.25h; Inert atmosphere; Stage #2: anethole In 1,2-dichloro-ethane for 62h; Inert atmosphere; Irradiation; regioselective reaction; | 99% |
Togni's reagent II
anethole
3,3,3-trifluoro-1-(4-methoxyphenyl)-2-methylpropan-1-one
Conditions | Yield |
---|---|
With tris[2-phenylpyridinato-C2,N]iridium(III); dimethyl sulfoxide at 20℃; for 2h; Irradiation; Green chemistry; | 99% |
With N9,N9,N10,N10-tetrakis(4-(tert-butyl)phenyl)anthracene-9,10-diamine; dimethyl sulfoxide In dichloromethane at 20℃; for 3h; Irradiation; | 75% |
With dmap; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; magnesium sulfate In dimethyl sulfoxide at 20℃; for 48h; Solvent; Reagent/catalyst; Inert atmosphere; Irradiation; | 40% |
anethole
isoprene
(1SR,2SR)-4'-methoxy-2,4-dimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl
Conditions | Yield |
---|---|
With N,N’,N’’-tris(3,5-bis(trifluoromethyl)phenyl)thiophosphoramide; [Ru(4,4'-bis(trifluoromethyl)-2,2'-bipyridine)3](3,5-bis(trifluoromethyl)benzenesulfonate)2 In dichloromethane at 20℃; for 0.333333h; Quantum yield; Reagent/catalyst; Diels-Alder Cycloaddition; Inert atmosphere; Irradiation; | 99% |
With tris(4-bromophenyl)ammoniumyl hexafluoroantimonate In dichloromethane for 1h; Quantum yield; Reagent/catalyst; Diels-Alder Cycloaddition; Irradiation; | 35% |
Conditions | Yield |
---|---|
With copper(ll) bromide In acetonitrile at 20℃; for 2h; Schlenk technique; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With copper(ll) bromide In acetonitrile at 20℃; for 2h; Schlenk technique; Inert atmosphere; | 99% |
anethole
2-(4-methoxyphenyl)-3-methyloxirane
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In acetone for 0.666667h; Ambient temperature; | 98% |
With dihydrogen peroxide; sodium hydrogencarbonate In acetonitrile | |
With oxidovanadium(IV)-β-octabromo-meso-tetrakis(2,6-dibromo-3,5-dimethoxyphenyl)porphyrin; dihydrogen peroxide; sodium hydrogencarbonate In water; acetonitrile at 60℃; for 0.5h; Catalytic behavior; Reagent/catalyst; |
Conditions | Yield |
---|---|
With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) In 1,2-dichloro-ethane at 0℃; for 6h; | 98% |
Conditions | Yield |
---|---|
Lewatit SP 120 (acid form) In 1,4-dioxane at 60℃; for 0.5h; | 97% |
With sulfuric acid |
4,4-dimethoxycyclohexa-2,5-dienone
anethole
2,3-dihydro-5-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran
Conditions | Yield |
---|---|
With polystyrene-supported perfluorobenzoic acid In dichloromethane; 1,1,1,3',3',3'-hexafluoro-propanol at 0℃; chemoselective reaction; | 97% |
With 1,1,1,3',3',3'-hexafluoro-propanol; Pentafluorobenzoic acid In dichloromethane at 25℃; for 0.166667h; | 93% |
Conditions | Yield |
---|---|
Stage #1: butyric acid With 2,6-dimethylpyridine; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; thiophenol In 1,2-dichloro-ethane at 0 - 23℃; for 0.25h; Inert atmosphere; Stage #2: anethole In 1,2-dichloro-ethane for 48h; Inert atmosphere; Irradiation; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
With copper(ll) bromide In acetonitrile at 20℃; for 2h; Solvent; Schlenk technique; Inert atmosphere; | 97% |
anethole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
(S)-2-(1-(4-methoxyphenyl)propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With C24H31Cl2FeN3O2; sodium triethylborohydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 97% |
With C26H28N4O; cobalt(II) acetate In diethyl ether at 20℃; for 18h; enantioselective reaction; | 87% |
C12H12O2
anethole
7-(3,3-dimethylbut-1-ynyl)-2-(4-methoxyphenyl)-2-methyl-2,3-dihydrobenzofuran-5-ol
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 0℃; Inert atmosphere; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
With C18H22N2O; copper(II) bis(trifluoromethanesulfonate) In toluene at -80℃; for 36h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 96% |
anethole
2-(4-methoxyphenyl)propanal
Conditions | Yield |
---|---|
With iodine; silver(l) oxide In 1,4-dioxane; water for 4h; Ambient temperature; | 95% |
With N-iodo-succinimide; water; cetyltrimethylammonim bromide In 1,4-dioxane at 20 - 105℃; for 0.333333h; Microwave irradiation; | 78% |
With N-Bromosuccinimide; water; cetyltrimethylammonim bromide In dimethyl sulfoxide at 200℃; for 0.2h; Microwave irradiation; | 65% |
anethole
A
2-(4-methoxyphenyl)-3-methyloxirane
B
2-(4-methoxyphenyl)propanal
Conditions | Yield |
---|---|
With iodine; silver(l) oxide In 1,4-dioxane; water for 4h; Product distribution; Ambient temperature; various bases, solvents and temp.; | A n/a B 95% |
With sodium hydroxide; iodine for 2h; Ambient temperature; | A 10 % Chromat. B n/a |
anethole
1,2-bis(4-methoxyphenyl)ethene
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In neat (no solvent) at 90℃; for 1.33333h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With copper(ll) bromide In acetonitrile at 20℃; for 2h; Schlenk technique; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With C18H22N2O; copper(II) bis(trifluoromethanesulfonate) In toluene at -80℃; for 36h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
With C18H22N2O; copper(II) bis(trifluoromethanesulfonate) In toluene at -80℃; for 36h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
With aluminum oxide; potassium permanganate In dichloromethane at 20℃; for 4h; | 94% |
With disodium hydrogenphosphate; oxygen; cobalt(II) acetate In methanol at 50℃; for 6h; | 89.9% |
With oxygen; ozone In water; ethyl acetate at 20℃; for 1.66667h; | 81.7% |
Conditions | Yield |
---|---|
Stage #1: benzoic acid With 2,6-dimethylpyridine; 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; thiophenol In 1,2-dichloro-ethane at 0 - 23℃; for 0.25h; Inert atmosphere; Stage #2: anethole In 1,2-dichloro-ethane for 30h; Inert atmosphere; Irradiation; regioselective reaction; | 94% |
Conditions | Yield |
---|---|
With trimethylsilylazide; water; dimethylglyoxal In toluene at 20℃; for 8h; Inert atmosphere; Schlenk technique; | 94% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 100℃; for 2h; | 93% |
Conditions | Yield |
---|---|
With C18H22N2O; copper(II) bis(trifluoromethanesulfonate) In toluene at -80℃; for 36h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 93% |
anethole
2-bromo-1-(4-methoxyphenyl)-1-propanone
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 25 - 35℃; for 0.3h; regioselective reaction; | 92% |
With dipotassium peroxodisulfate; potassium bromide In water at 60℃; for 12h; Green chemistry; | 21% |
With bromine; ethyl acetate for 2h; | 3.9% |
Multi-step reaction with 2 steps 1: absolute diethyl ether; bromine 2: CrO3; glacial acetic acid View Scheme |
The Molecular formula of p-PROPENYLANISOLE(104-46-1):C10H12O
The Molecular Weight of p-PROPENYLANISOLE(104-46-1):148.2
The Molecular Structure of p-PROPENYLANISOLE(104-46-1) is:
Melting point:20-21 °C(lit.)
Boiling point:237.5 °C at 760 mmHg
Flash point:88.4 °C
Solubility in water:slightly water soluble .
Index of Refraction:1.545
Molar Refractivity:48.82 cm3
Molar Volume:154.4 cm3
Polarizability:19.35 10-24cm3
Surface Tension:31.8 dyne/cm
Enthalpy of Vaporization:45.51 kJ/mol
Vapour Pressure:0.0687 mmHg at 25°C
Appearance:white crystals or a liquid
IUPAC Name:1-methoxy-4-[(E)-prop-1-enyl]benzene
Synonyms:P-METHOXYPROPENYLBENZENE;P-PROPENYLPHENYL METHYL ETHER;TRANS-1-METHOXY-4-(1-PROPENYL)BENZENE;TRANS-P-METHOXYPROPENYLBENZENE;TRANS-P-PROPENYLANISOLE;FEMA 2086;(E)-1-METHOXY-4-(1-PROPENYL)BENZENE;PARA METHOXY ALPHA PHENYL PROPENE
1. | orl-rat LD50:2090 mg/kg | FCTXAV Food and Cosmetics Toxicology. 2 (1964),327. | ||
2. | orl-mus LD50:3050 mg/kg | FCTXAV Food and Cosmetics Toxicology. 2 (1964),327. | ||
3. | orl-gpg LD50:2160 mg/kg | FCTXAV Food and Cosmetics Toxicology. 2 (1964),327. | ||
4. | orl-bwd LD50:316 mg/kg | AECTCV Archives of Environmental Contamination and Toxicology. 12 (1983),355. |
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