Conditions | Yield |
---|---|
With hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30003 Torr; for 96h; Reagent/catalyst; Autoclave; | 100% |
With hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30402 Torr; for 18h; Catalytic behavior; Reagent/catalyst; Glovebox; Inert atmosphere; | 100% |
With borane-ammonia complex; Pd(SIPr)(PCy3) In isopropyl alcohol at 50℃; for 16h; Inert atmosphere; Glovebox; | 99% |
Conditions | Yield |
---|---|
With magnesium; nickel dichloride In water at 20℃; for 12h; Sealed tube; Photolysis; Inert atmosphere; | 99% |
With oxygen; hydrazine hydrate In propan-1-ol at 120℃; under 15001.5 Torr; for 0.5h; | 91% |
With oxygen; hydrazine hydrate In propan-1-ol at 120℃; under 15001.5 Torr; for 0.166667h; Flow reactor; | 91% |
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% |
1-methanesulfonyloxy-3-(4-methoxyphenyl)propane
4-n-propylanisole
Conditions | Yield |
---|---|
With samarium diiodide; tri-n-butyl-tin hydride; lithium iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20 - 35℃; for 21h; Elimination; | 95% |
2-phenyl-1,3,2-benzodioxaborole
E-1-(4'-methoxyphenyl)prop-1-ene
A
4-n-propylanisole
B
phenol
Conditions | Yield |
---|---|
With oxygen; hydrazine hydrate In acetonitrile at 32℃; under 760.051 Torr; for 5h; Schlenk technique; | A 95% B 91% |
Conditions | Yield |
---|---|
Stage #1: propyl bromide With chloro-trimethyl-silane; diisobutylaluminium hydride; magnesium; 1-Bromo-2-chloroethane In tetrahydrofuran at 40℃; Flow reactor; Stage #2: With 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Flow reactor; Stage #3: 4-chloromethoxybenzene With iron(III)-acetylacetonate In tetrahydrofuran at 25℃; for 0.333333h; Inert atmosphere; Flow reactor; Irradiation; | 95% |
1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonic acid 4-methoxyphenyl ester
propyl bromide
4-n-propylanisole
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 5-(dicyclohexylphosphaneyl)-1-(2,6-diisopropoxyphenyl)-1H-pyrazole; magnesium; lithium chloride; zinc(II) chloride In tetrahydrofuran at 25℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction; | 93% |
Conditions | Yield |
---|---|
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction; | 89% |
Conditions | Yield |
---|---|
With palladium diacetate; zinc dibromide; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 20 - 25℃; for 2.5h; Inert atmosphere; | 88% |
Estragole
A
(Z)-1-(4-tolyl)-1-propene
B
(E)-1-methyl-4-(prop-1-enyl)benzene
C
4-n-propylanisole
Conditions | Yield |
---|---|
With iron(III) chloride; lithium aluminium tetrahydride; hydrogen In tetrahydrofuran at 18℃; under 750.075 Torr; for 24h; Inert atmosphere; Sealed tube; | A n/a B n/a C 84% |
4-(p-methoxyphenyl)but-1-ene
4-n-propylanisole
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; ethanol; phenylsilane; thiophenol In propan-1-ol at 23℃; for 108h; Inert atmosphere; | 83% |
isopropyl chloride
4-methoxyphenyl triflate
A
4-n-propylanisole
B
1-methoxy-4-(1-methylethyl)benzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dibutylphosphanyl)-1-phenylpyrrole; magnesium; lithium chloride; zinc(II) chloride In tetrahydrofuran at 60℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; | A 76% B n/a |
Conditions | Yield |
---|---|
With palladium diacetate; zinc dibromide; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 20 - 25℃; for 2.5h; Inert atmosphere; | 72% |
cyclopropyl bromide
3-(4-methoxyphenyl)-1-iodopropane
A
4-n-propylanisole
Conditions | Yield |
---|---|
Stage #1: cyclopropyl bromide With iodine; magnesium In 2-methyltetrahydrofuran for 1.5h; Inert atmosphere; Reflux; Stage #2: 3-(4-methoxyphenyl)-1-iodopropane With N,N,N,N,-tetramethylethylenediamine; cobalt(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; for 1h; Inert atmosphere; chemoselective reaction; | A 6% B 69% |
Conditions | Yield |
---|---|
With C9H24B11N2(1+)*C24BF20(1-); hydrogen In benzene at 80℃; for 24h; Autoclave; | 69% |
4-methoxyphenyl triflate
isopropyl bromide
A
4-n-propylanisole
B
1-methoxy-4-(1-methylethyl)benzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dibutylphosphanyl)-1-phenylpyrrole; magnesium; lithium chloride; zinc(II) chloride In tetrahydrofuran at 60℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; | A 68% B n/a |
4-methoxy-α-ethylbenzyl methyl ether
4-n-propylanisole
Conditions | Yield |
---|---|
With triethylsilane; iron(III) chloride In dichloromethane at 20℃; for 1.5h; | 66% |
With triethylsilane; iron(III) chloride In dichloromethane at 20℃; for 1.5h; | 66% |
Estragole
carbon monoxide
A
4-n-propylanisole
B
3-(p-methoxyphenyl)-2-methylpropionaldehyde
C
4-(4-methoxyphenyl)butyraldehyde
D
E-1-(4'-methoxyphenyl)prop-1-ene
Conditions | Yield |
---|---|
With hydrogen; N-dodecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide; {Rh(cod)[μ-S(CH2)3Si(OMe)3]}2; triphenylphosphine In water; butan-1-ol at 80℃; under 10350.8 Torr; for 6h; microemulsion/sol-gel; Further byproducts given; | A 1.4% B 27.4% C 63.8% D 6.7% |
Conditions | Yield |
---|---|
With palladium diacetate; zinc dibromide; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 20 - 25℃; for 2.5h; Inert atmosphere; | 63% |
Conditions | Yield |
---|---|
With potassium carbonate In 1,2-dimethoxyethane at 145℃; for 0.416667h; Microwave irradiation; Inert atmosphere; Sealed vessel; | 61% |
O-[3-(4-meethoxyphenyl)propyl] O-phenyl thiocarbonate
4-n-propylanisole
Conditions | Yield |
---|---|
With di-tert-butyl peroxide; tris-(trimethylsilyl)silane In benzene at 135℃; for 2h; Barton-McCombie deoxygenation; Inert atmosphere; | 60% |
cyclopropyl bromide
3-(4-methoxyphenyl)-1-iodopropane
A
Estragole
B
4-n-propylanisole
D
E-1-(4'-methoxyphenyl)prop-1-ene
Conditions | Yield |
---|---|
Stage #1: cyclopropyl bromide With iodine; magnesium In 2-methyltetrahydrofuran for 1.5h; Inert atmosphere; Reflux; Stage #2: 3-(4-methoxyphenyl)-1-iodopropane With N,N,N,N,-tetramethylethylenediamine; cobalt(II) aceylacetonate In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; for 1h; Inert atmosphere; chemoselective reaction; | A 15% B 7% C 45% D 10% |
Stage #1: cyclopropyl bromide With iodine; magnesium In 2-methyltetrahydrofuran for 1.5h; Inert atmosphere; Reflux; Stage #2: 3-(4-methoxyphenyl)-1-iodopropane With cobalt(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; for 1h; Inert atmosphere; chemoselective reaction; | A 10% B 13% C 16% D 7% |
4-methoxy-trans-cinnamaldehyde
A
4-n-propylanisole
B
3-(4-methoxyphenyl)propional
C
3-(p-methoxyphenyl)-1-propanol
Conditions | Yield |
---|---|
With methanol; formic acid; water; silica gel; palladium dichloride for 0.9h; Irradiation; microwave; | A 36% B 8% C 44% |
cyclopropyl bromide
3-(4-methoxyphenyl)-1-iodopropane
A
4-n-propylanisole
C
E-1-(4'-methoxyphenyl)prop-1-ene
Conditions | Yield |
---|---|
Stage #1: cyclopropyl bromide With iodine; magnesium In 2-methyltetrahydrofuran for 1.5h; Inert atmosphere; Reflux; Stage #2: 3-(4-methoxyphenyl)-1-iodopropane With (1R,2R)-1,2,3,3-tetramethyl-1,2-cyclohexanediamine; cobalt(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; for 1h; Reagent/catalyst; Inert atmosphere; chemoselective reaction; | A 11% B 42% C 28% |
1-bromo-4-methoxy-benzene
isopropylmagnesium chloride
A
4-n-propylanisole
B
1-methoxy-4-(1-methylethyl)benzene
Conditions | Yield |
---|---|
With N,N,N'N'-tetramethyl-1,3-propanediamine; 1,3-bis(mesityl)imidazolium chloride; cobalt(II) chloride In diethyl ether at 25℃; for 1h; Inert atmosphere; | A 34% B 9% |
cyclopropyl bromide
3-(4-methoxyphenyl)-1-iodopropane
A
Estragole
B
4-n-propylanisole
Conditions | Yield |
---|---|
Stage #1: cyclopropyl bromide With iodine; magnesium In 2-methyltetrahydrofuran for 1.5h; Inert atmosphere; Reflux; Stage #2: 3-(4-methoxyphenyl)-1-iodopropane With iron(III) chloride; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; for 1h; Inert atmosphere; chemoselective reaction; | A 19% B 15% C 32% |
carbon monoxide
anethole
A
4-(4-methoxyphenyl)butan-1-ol
B
4-n-propylanisole
C
2-(4-Methoxy-phenyl)-butan-1-ol
Conditions | Yield |
---|---|
With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); dicarbonylacetylacetonatorhodium(I); tris[(R)-2’-(benzyloxy)-1,1’-binaphthyl-2-yl]phosphite; hydrogen In toluene at 120℃; under 30003 Torr; for 20h; Autoclave; | A n/a B 16% C n/a |
Estragole
A
cis-Anethole
B
4-n-propylanisole
C
E-1-(4'-methoxyphenyl)prop-1-ene
Conditions | Yield |
---|---|
With borane-ammonia complex; [Fe(nacnac)dippCH2SiMe3] In benzene-d6 at 60℃; for 16h; Inert atmosphere; Glovebox; Overall yield = 62 percent; Overall yield = 45.9 mg; Optical yield = 80.769 percent de; | A n/a B 15% C n/a |
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II) In isopropyl alcohol at 20℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube; |
para-iodoanisole
propyl zinc chloride
A
4-n-propylanisole
B
methoxybenzene
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; diethyl ether at 20℃; for 3h; | A 94 % Spectr. B 5% |
4-n-butylanisole
4-n-propylanisole
Conditions | Yield |
---|---|
at 310 - 320℃; im Rohr; | |
at 310 - 320℃; im mit Stickstoff gefuellten Rohr; |
Conditions | Yield |
---|---|
Stage #1: 4-n-propylanisole; acetyl chloride With aluminum (III) chloride In dichloromethane at -10℃; for 0.5h; Stage #2: With hydrogenchloride In dichloromethane; water | 100% |
Stage #1: 4-n-propylanisole; acetyl chloride With aluminum (III) chloride In dichloromethane at -10℃; for 0.5h; Friedel Crafts Acylation; Stage #2: With hydrogenchloride; water In dichloromethane at 0℃; |
Conditions | Yield |
---|---|
With [CuCl(ClIPr)]; sodium t-butanolate; tert-butyl alcohol In tetrahydrofuran; hexane at 40℃; for 20h; Inert atmosphere; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; copper(I) sulfate In water; acetonitrile at 65 - 70℃; for 3h; | 85% |
With formic acid; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 110 - 120℃; for 0.266667h; microwave irradiation; | 66% |
With Bromotrichloromethane; Ir[2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine]2(4,4'-di-tert-butyl-2,2'-bipyridine)PF6; water; potassium carbonate In acetonitrile at 20℃; Irradiation; Inert atmosphere; regioselective reaction; | 60% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; water at 35 - 40℃; for 10h; Wohl-Ziegler Bromination; Irradiation; | 82% |
1,2,3-Benzotriazole
4-n-propylanisole
1-(1-(4-methoxyphenyl)propyl)-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With Bromotrichloromethane; Ir[2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine]2(4,4'-di-tert-butyl-2,2'-bipyridine)PF6; potassium carbonate In acetonitrile at 20℃; Irradiation; Inert atmosphere; regioselective reaction; | 80% |
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone for 1.16667h; sonication; | 74% |
4-n-propylanisole
4-methoxy-trans-cinnamaldehyde
Conditions | Yield |
---|---|
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 2h; | 72% |
Conditions | Yield |
---|---|
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane Microwave irradiation; | 70% |
4-n-propylanisole
A
4-methoxycinnamaldehyde
B
4-methoxy-trans-cinnamaldehyde
Conditions | Yield |
---|---|
With bunazosin In 1,4-dioxane | A 68% B n/a |
Conditions | Yield |
---|---|
With 2-Iodobenzoic acid; potassium peroxomonosulfate; water In acetonitrile for 8h; | A 6% B 64% |
4-n-propylanisole
Conditions | Yield |
---|---|
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; sodium hydrogencarbonate In acetonitrile at 20℃; Schlenk technique; Inert atmosphere; Molecular sieve; Irradiation; | 62% |
IUPAC Name:1-Methoxy-4-propylbenzene
Synonyms: Dihydroanethole ; Fema 2930 ; 4-Propylanisole ; 4-N-Propylanisole ; 1-Methoxy-4-propylbenzene ; Timtec-bb sbb007737 ; P-propyl anisole ; 1-Methoxy-4-propyl-benzen
CAS NO: 104-45-0
Molecular Formula:C10H14O
Molecular Weight: 150.22
Molecular Structure:
EINECS: 203-203-4
FEMA : 2930
Mol File: 104-45-0.mol
Index of Refraction: 1.49
Surface Tension: 29.8 dyne/cm
Density: 0.922 g/cm3
Flash Point: 82.3 °C
Enthalpy of Vaporization: 42.94 kJ/mol
Boiling Point: 211.4 °C at 760 mmHg
Vapour Pressure: 0.266 mmHg at 25°C
Appearance: P-N-Propyl anisole (CAS NO. 104-45-0) is colorless to pale yellow liquid.
Solubility: P-N-Propyl anisole (CAS NO. 104-45-0) is soluble in ethanol, the majority of non-volatile oil and mineral oil, insoluble in glycerin and propylene glycol.
P-N-Propyl anisole (CAS NO. 104-45-0) is used as spices, mainly for the preparation of beer flavor.
anethole in the nickel catalyst at the 60 ~ 95 ℃ and pressure, formed under the conditions of partial hydrogenation.
1. | sln-dmg-orl 5 mmol/L | FCTOD7 Food and Chemical Toxicology. 21 (1983),707. | ||
2. | orl-rat LD50:4400 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),378. | ||
3. | orl-mus LD50:7300 mg/kg | FCTXAV Food and Cosmetics Toxicology. 2 (1964),327. |
Reported in EPA TSCA Inventory.
Mildly toxic by ingestion. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes N
Risk Statements 51/53
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements 61
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
WGK Germany 2
RTECS BZ9450000
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