Product Name

  • Name

    Anethole

  • EINECS 203-205-5
  • CAS No. 104-46-1
  • Article Data69
  • CAS DataBase
  • Density 0.988 g/mL at 25 °C(lit.)
  • Solubility
  • Melting Point 20-21 °C(lit.)
  • Formula C10H12O
  • Boiling Point 237.5 °C at 760 mmHg
  • Molecular Weight 148.205
  • Flash Point 88.4 °C
  • Transport Information
  • Appearance Colourless,clear, liquid
  • Safety 36/37
  • Risk Codes 43
  • Molecular Structure Molecular Structure of 104-46-1 (Anethole)
  • Hazard Symbols IrritantXi
  • Synonyms Anise camphor;Isoestragole;NSC 4018;Nauli gum;Oil of aniseed;p-1-Propenylanisole;p-Anethole;p-Methoxy-b-methylstyrene;p-Propenylanisole;p-Propenylphenyl methyl ether;Anisole,p-propenyl- (8CI);Benzene, 1-methoxy-4-(1-propenyl)- (9CI);1-Methoxy-4-(1-propenyl)benzene;1-Methoxy-4-propenylbenzene;1-Propene,1-(4-methoxyphenyl)-;4-(1-Propenyl)anisole;4-Methoxy-1-propenylbenzene;4-Methoxypropenylbenzene;4-Propenylanisole;Anethol;
  • PSA 9.23000
  • LogP 2.72830

Synthetic route

4-[(Z)-2-dodecylthioethenyl]anisole
863775-00-2

4-[(Z)-2-dodecylthioethenyl]anisole

methylmagnesium bromide
75-16-1

methylmagnesium bromide

anethole
104-46-1

anethole

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride In diethyl ether for 12h; Heating;90%
C16H22N2O

C16H22N2O

A

3,4,5-Trimethylpyrazole
5519-42-6

3,4,5-Trimethylpyrazole

B

anethole
104-46-1

anethole

Conditions
ConditionsYield
With organo lithium reagent In hexane at 20℃; for 24h;A 80%
B 86%
1-bromo-1-propene
590-14-7

1-bromo-1-propene

4-methoxyphenylmagnesium chloride
699-19-4

4-methoxyphenylmagnesium chloride

anethole
104-46-1

anethole

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; cobalt acetylacetonate In tetrahydrofuran at 15 - 20℃; for 0.25h;80%
ethyl 1-propenyl ether
928-55-2

ethyl 1-propenyl ether

4-methoxyphenyl magnesium bromide
13139-86-1

4-methoxyphenyl magnesium bromide

anethole
104-46-1

anethole

Conditions
ConditionsYield
With C68H72Cl2N6NiP2 In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;77%
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

anethole
104-46-1

anethole

Conditions
ConditionsYield
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
74568-53-9

(E)-methyl 3-(3-bromo-4-hydroxyphenyl)acrylate

A

Estragole
140-67-0

Estragole

B

trans-2-bromo-4-(3-hydroxypropen-1-yl)phenol
74568-54-0

trans-2-bromo-4-(3-hydroxypropen-1-yl)phenol

C

anethole
104-46-1

anethole

Conditions
ConditionsYield
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
24393-56-4, 51507-22-3, 1929-30-2

ethyl p-methoxycinnamate

A

Estragole
140-67-0

Estragole

B

p-methoxycinnamyl alcohol
53484-50-7, 17581-85-0

p-methoxycinnamyl alcohol

C

anethole
104-46-1

anethole

Conditions
ConditionsYield
With aluminium hydride In diethyl ether for 0.5h; Ambient temperature; Yields of byproduct given;A n/a
B 47%
C n/a
carbonic acid 1-(4-methoxy-phenyl)-allyl ester methyl ester

carbonic acid 1-(4-methoxy-phenyl)-allyl ester methyl ester

anethole
104-46-1

anethole

Conditions
ConditionsYield
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%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

1-bromo-1-propene
590-14-7

1-bromo-1-propene

anethole
104-46-1

anethole

Conditions
ConditionsYield
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 70℃; i = 250 mA, nickel-sponge cathode;44%
Estragole
140-67-0

Estragole

A

1-methoxy-4-(4-(p-methoxyphenyl)but-3-enyl)benzene
87797-12-4

1-methoxy-4-(4-(p-methoxyphenyl)but-3-enyl)benzene

B

4,4'-dimethoxystilbene
4705-34-4

4,4'-dimethoxystilbene

C

1,3-bis(4-methoxyphenyl)prop-1-ene
34414-53-4

1,3-bis(4-methoxyphenyl)prop-1-ene

D

anethole
104-46-1

anethole

E

1,4-bis(4-methoxyphenyl)but-2-ene

1,4-bis(4-methoxyphenyl)but-2-ene

Conditions
ConditionsYield
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%
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

anethole
104-46-1

anethole

Conditions
ConditionsYield
With trityl tetrafluoroborate In dichloromethane at -78℃; for 30h;15%
pyridine
110-86-1

pyridine

1-(4-methoxyphenyl)prop-1-yl acetate
16031-55-3

1-(4-methoxyphenyl)prop-1-yl acetate

anethole
104-46-1

anethole

Estragole
140-67-0

Estragole

anethole
104-46-1

anethole

Conditions
ConditionsYield
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;
[1-(4-methoxy-phenyl)-propyl]-dimethyl-amine

[1-(4-methoxy-phenyl)-propyl]-dimethyl-amine

acetic anhydride
108-24-7

acetic anhydride

A

N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

B

1-(4-methoxyphenyl)prop-1-yl acetate
16031-55-3

1-(4-methoxyphenyl)prop-1-yl acetate

C

anethole
104-46-1

anethole

ethylmagnesium iodide
10467-10-4

ethylmagnesium iodide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

anethole
104-46-1

anethole

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

propionic acid anhydride
123-62-6

propionic acid anhydride

anethole
104-46-1

anethole

Conditions
ConditionsYield
With sodium proprionate
propene
187737-37-7

propene

(4-Methoxyphenyl)mercuric acetate
5780-90-5

(4-Methoxyphenyl)mercuric acetate

A

Estragole
140-67-0

Estragole

B

1-isopropenyl-4-methoxybenzene
1712-69-2

1-isopropenyl-4-methoxybenzene

C

anethole
104-46-1

anethole

Conditions
ConditionsYield
(i) Pd(OAc)2, MeCN, (ii) /BRN= 1696878/; Multistep reaction;
Estragole
140-67-0

Estragole

A

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

B

anethole
104-46-1

anethole

Conditions
ConditionsYield
With H2O2 or O2; copper dichloride; palladium dichloride In ethanol
ethyltriphenylphosphonium bromide
1530-32-1

ethyltriphenylphosphonium bromide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

anethole
104-46-1

anethole

Conditions
ConditionsYield
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;
Benzylidene-tris-(4-methoxy-phenyl)-λ5-phosphane
75619-30-6

Benzylidene-tris-(4-methoxy-phenyl)-λ5-phosphane

acetaldehyde
75-07-0

acetaldehyde

anethole
104-46-1

anethole

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 1h;52 % Chromat.
1-(2-Diazo-1-methyl-ethyl)-4-methoxy-benzene

1-(2-Diazo-1-methyl-ethyl)-4-methoxy-benzene

A

1-isopropenyl-4-methoxybenzene
1712-69-2

1-isopropenyl-4-methoxybenzene

B

4-methoxyphenylcyclopropane
4030-17-5

4-methoxyphenylcyclopropane

C

anethole
104-46-1

anethole

Conditions
ConditionsYield
at 160℃; Yield given. Yields of byproduct given;
α-methyl-β-<4-methoxy-phenyl>-acrylic acid

α-methyl-β-<4-methoxy-phenyl>-acrylic acid

anethole
104-46-1

anethole

ethyl-<4-methoxy-phenyl>-carbinol

ethyl-<4-methoxy-phenyl>-carbinol

anethole
104-46-1

anethole

Conditions
ConditionsYield
With sulfuric acid durch Destillation;
ethyl-<4-methoxy-phenyl>--methyl-acetate

ethyl-<4-methoxy-phenyl>--methyl-acetate

anethole
104-46-1

anethole

Conditions
ConditionsYield
With potassium carbonate
With pyridine
p-allyl-anisole

p-allyl-anisole

anethole
104-46-1

anethole

Conditions
ConditionsYield
With potassium hydroxide
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl magnesium halide (excessive)

ethyl magnesium halide (excessive)

A

anethole
104-46-1

anethole

B

polymer(ic) anethole

polymer(ic) anethole

Estragole
140-67-0

Estragole

concentrated alcoholic KOH-solution

concentrated alcoholic KOH-solution

anethole
104-46-1

anethole

Estragole
140-67-0

Estragole

infusorial earht

infusorial earht

anethole
104-46-1

anethole

Conditions
ConditionsYield
at 500℃;
1-(4-methoxyphenyl)prop-1-yl acetate
16031-55-3

1-(4-methoxyphenyl)prop-1-yl acetate

alcoholic KOH-solution

alcoholic KOH-solution

anethole
104-46-1

anethole

anethole
104-46-1

anethole

4-n-propylanisole
104-45-0

4-n-propylanisole

Conditions
ConditionsYield
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%
anethole
104-46-1

anethole

1-(1,2-dibromopropyl)-4-methoxybenzene
1201-60-1

1-(1,2-dibromopropyl)-4-methoxybenzene

Conditions
ConditionsYield
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
89845-28-3

2-(2-phenylethynyl)-1,4-benzoquinone

anethole
104-46-1

anethole

2-(4-methoxyphenyl)-2-methyl-7-(phenylethynyl)-2,3-dihydrobenzofuran-5-ol
1432504-68-1

2-(4-methoxyphenyl)-2-methyl-7-(phenylethynyl)-2,3-dihydrobenzofuran-5-ol

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 0℃; Inert atmosphere; Schlenk technique;99%
propionic acid
802294-64-0

propionic acid

anethole
104-46-1

anethole

1-(4-methoxyphenyl)propan-2-yl propionate
1446122-90-2

1-(4-methoxyphenyl)propan-2-yl propionate

Conditions
ConditionsYield
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%
isobutyric Acid
79-31-2

isobutyric Acid

anethole
104-46-1

anethole

isobutyric acid 2-(4-methoxyphenyl)-1-methylethyl ester

isobutyric acid 2-(4-methoxyphenyl)-1-methylethyl ester

Conditions
ConditionsYield
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
887144-94-7

Togni's reagent II

anethole
104-46-1

anethole

3,3,3-trifluoro-1-(4-methoxyphenyl)-2-methylpropan-1-one
1610846-52-0

3,3,3-trifluoro-1-(4-methoxyphenyl)-2-methylpropan-1-one

Conditions
ConditionsYield
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
104-46-1

anethole

isoprene
78-79-5

isoprene

(1SR,2SR)-4'-methoxy-2,4-dimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl
112150-17-1

(1SR,2SR)-4'-methoxy-2,4-dimethyl-1,2,3,6-tetrahydro-1,1'-biphenyl

Conditions
ConditionsYield
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%
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

anethole
104-46-1

anethole

(4-fluorophenyl)(1-(4-methoxyphenyl)propyl)sulfane

(4-fluorophenyl)(1-(4-methoxyphenyl)propyl)sulfane

Conditions
ConditionsYield
With copper(ll) bromide In acetonitrile at 20℃; for 2h; Schlenk technique; Inert atmosphere;99%
p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

anethole
104-46-1

anethole

(4-chlorophenyl)(1-(4-methoxyphenyl)propyl)sulfane

(4-chlorophenyl)(1-(4-methoxyphenyl)propyl)sulfane

Conditions
ConditionsYield
With copper(ll) bromide In acetonitrile at 20℃; for 2h; Schlenk technique; Inert atmosphere;99%
anethole
104-46-1

anethole

2-(4-methoxyphenyl)-3-methyloxirane
51410-46-9

2-(4-methoxyphenyl)-3-methyloxirane

Conditions
ConditionsYield
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;
ethyl diazoalaninate
6111-99-5

ethyl diazoalaninate

anethole
104-46-1

anethole

5-ethoxy-2-(4-methoxyphenyl)-3,4-dimethyl-2,3-dihydrofuran

5-ethoxy-2-(4-methoxyphenyl)-3,4-dimethyl-2,3-dihydrofuran

Conditions
ConditionsYield
With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) In 1,2-dichloro-ethane at 0℃; for 6h;98%
formaldehyd
50-00-0

formaldehyd

anethole
104-46-1

anethole

4-p-methoxyphenyl-5-methyl-1,3-dioxane
5689-72-5

4-p-methoxyphenyl-5-methyl-1,3-dioxane

Conditions
ConditionsYield
Lewatit SP 120 (acid form) In 1,4-dioxane at 60℃; for 0.5h;97%
With sulfuric acid
4,4-dimethoxycyclohexa-2,5-dienone
935-50-2

4,4-dimethoxycyclohexa-2,5-dienone

anethole
104-46-1

anethole

2,3-dihydro-5-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran
1326704-90-8

2,3-dihydro-5-methoxy-2-(4-methoxyphenyl)-3-methylbenzofuran

Conditions
ConditionsYield
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%
anethole
104-46-1

anethole

butyric acid
107-92-6

butyric acid

1-(4-methoxyphenyl)propan-2-yl butyrate
183471-68-3

1-(4-methoxyphenyl)propan-2-yl butyrate

Conditions
ConditionsYield
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%
para-thiocresol
106-45-6

para-thiocresol

anethole
104-46-1

anethole

(1-(4-methoxyphenyl)propyl)(p-tolyl)sulfane

(1-(4-methoxyphenyl)propyl)(p-tolyl)sulfane

Conditions
ConditionsYield
With copper(ll) bromide In acetonitrile at 20℃; for 2h; Solvent; Schlenk technique; Inert atmosphere;97%
anethole
104-46-1

anethole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

(S)-2-(1-(4-methoxyphenyl)propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1589553-46-7

(S)-2-(1-(4-methoxyphenyl)propyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
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
1447990-65-9

C12H12O2

anethole
104-46-1

anethole

7-(3,3-dimethylbut-1-ynyl)-2-(4-methoxyphenyl)-2-methyl-2,3-dihydrobenzofuran-5-ol
1432504-78-3

7-(3,3-dimethylbut-1-ynyl)-2-(4-methoxyphenyl)-2-methyl-2,3-dihydrobenzofuran-5-ol

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 0℃; Inert atmosphere; Schlenk technique;96%
3,6-Dioxo-cyclohexa-1,4-dienecarboxylic acid isopropyl ester
143427-14-9

3,6-Dioxo-cyclohexa-1,4-dienecarboxylic acid isopropyl ester

anethole
104-46-1

anethole

C20H22O5

C20H22O5

Conditions
ConditionsYield
With C18H22N2O; copper(II) bis(trifluoromethanesulfonate) In toluene at -80℃; for 36h; Schlenk technique; Inert atmosphere; enantioselective reaction;96%
anethole
104-46-1

anethole

2-(4-methoxyphenyl)propanal
252058-33-6, 305820-74-0

2-(4-methoxyphenyl)propanal

Conditions
ConditionsYield
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
104-46-1

anethole

A

2-(4-methoxyphenyl)-3-methyloxirane
51410-46-9

2-(4-methoxyphenyl)-3-methyloxirane

B

2-(4-methoxyphenyl)propanal
252058-33-6, 305820-74-0

2-(4-methoxyphenyl)propanal

Conditions
ConditionsYield
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
Conditions
ConditionsYield
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%
para-bromobenzenethiol
106-53-6

para-bromobenzenethiol

anethole
104-46-1

anethole

(4-bromophenyl)(1-(4-methoxyphenyl)propyl)sulfane

(4-bromophenyl)(1-(4-methoxyphenyl)propyl)sulfane

Conditions
ConditionsYield
With copper(ll) bromide In acetonitrile at 20℃; for 2h; Schlenk technique; Inert atmosphere;95%
C11H12O4

C11H12O4

anethole
104-46-1

anethole

C21H24O5

C21H24O5

Conditions
ConditionsYield
With C18H22N2O; copper(II) bis(trifluoromethanesulfonate) In toluene at -80℃; for 36h; Schlenk technique; Inert atmosphere; enantioselective reaction;95%
methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate
3958-79-0

methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate

anethole
104-46-1

anethole

C18H18O5

C18H18O5

Conditions
ConditionsYield
With C18H22N2O; copper(II) bis(trifluoromethanesulfonate) In toluene at -80℃; for 36h; Schlenk technique; Inert atmosphere; enantioselective reaction;95%
anethole
104-46-1

anethole

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
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%
benzoic acid
65-85-0

benzoic acid

anethole
104-46-1

anethole

1-(4-methoxyphenyl)propan-2-yl benzoate
1325210-54-5

1-(4-methoxyphenyl)propan-2-yl benzoate

Conditions
ConditionsYield
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%
di-tert-butyl-diazodicarboxylate
870-50-8

di-tert-butyl-diazodicarboxylate

anethole
104-46-1

anethole

di-tert-butyl 1-(2-azido-1-(4-methoxyphenyl)propyl)-hydrazine-1,2-dicarboxylate

di-tert-butyl 1-(2-azido-1-(4-methoxyphenyl)propyl)-hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With trimethylsilylazide; water; dimethylglyoxal In toluene at 20℃; for 8h; Inert atmosphere; Schlenk technique;94%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

anethole
104-46-1

anethole

C18H15NO4

C18H15NO4

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 100℃; for 2h;93%
2-ethoxycarbonyl-1,4-benzoquinone
62830-98-2

2-ethoxycarbonyl-1,4-benzoquinone

anethole
104-46-1

anethole

C19H20O5

C19H20O5

Conditions
ConditionsYield
With C18H22N2O; copper(II) bis(trifluoromethanesulfonate) In toluene at -80℃; for 36h; Schlenk technique; Inert atmosphere; enantioselective reaction;93%
anethole
104-46-1

anethole

2-bromo-1-(4-methoxyphenyl)-1-propanone
21086-33-9

2-bromo-1-(4-methoxyphenyl)-1-propanone

Conditions
ConditionsYield
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

cis-Anethol Chemical Properties

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

cis-Anethol Uses

It used as a toothpaste flavor, spice, also used for food, medicine, etc.   

cis-Anethol Toxicity Data With Reference

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.

cis-Anethol Consensus Reports

Reported in EPA TSCA Inventory.

cis-Anethol Safety Profile

Poison by ingestion. Questionable carcinogen with experimental tumorigenic data. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHERS.
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