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104-46-1 Usage

General Description

Anethole, also known as anise camphora, is a type of chemical compound with a pleasant, sweet aromatic scent, similar to anise or licorice. It's classified under the phenylpropene class of chemical compounds which are organic and aromatic in nature. Anethole is found naturally in various plants and spices, including star anise, fennel, and anise plants, from which it derives its name. This chemical compound is widely used as a flavoring substance due to its pleasant aroma and sweet taste. In addition to its use in culinary applications, anethole also possesses antimicrobial properties, making it a useful ingredient in certain medicinal formulations. It is also quite safe, as it is shown to be not harmful to humans when consumed in moderate amounts.

Check Digit Verification of cas no

The CAS Registry Mumber 104-46-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 104-46:
(5*1)+(4*0)+(3*4)+(2*4)+(1*6)=31
31 % 10 = 1
So 104-46-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O/c1-3-10(11-2)9-7-5-4-6-8-9/h3-8H,1-2H3

104-46-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name anethole

1.2 Other means of identification

Product number -
Other names cis-Anethol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-46-1 SDS

104-46-1Synthetic 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

104-46-1Related news

Anethole (cas 104-46-1) potentiates dodecanol's fungicidal activity by reducing PDR5 expression in budding yeast08/18/2019

Backgroundtrans-Anethole (anethole), a major component of anise oil, has a broad antimicrobial spectrum and a weaker antimicrobial potency than other available antibiotics. When combined with polygodial, nagilactone E, and n-dodecanol, anethole has been shown to exhibit synergistic antifungal ac...detailed

Synergistic effects of Anethole (cas 104-46-1) and ibuprofen in acute inflammatory response08/16/2019

This study assessed the effect of the combination of anethole and ibuprofen in comparison with monotherapy by either drug alone, using two in vivo inflammatory models, namely the pleurisy and paw edema in rats. We also measured the levels of the TNF protein in plasma, and the ability of anethole...detailed

Evaluation of encapsulated Anethole (cas 104-46-1) and carvone in lambs artificially- and naturally-infected with Haemonchus contortus08/12/2019

Molecules from natural sources, such as essential oils, have shown activity against parasites in vitro, but have not yet been explored extensively in vivo. Anethole and carvone (10% each), encapsulated with 80% of a solid matrix, referred to as EO (encapsulated oils), were tested in vivo in 2 ex...detailed

Original research articleThe concentration-dependent effect of Anethole (cas 104-46-1) on collagen, MMP-2 and GAG in human skin fibroblast cultures08/11/2019

PurposeIn aging skin and some skin disorders, components of skin extracellular matrix (ECM) are disturbed and therefore research to find skin drugs is important. Evaluation of anethole impact on collagen, GAGs and MMP-2 in human skin fibroblasts was the aim of this study.detailed

104-46-1Relevant articles and documents

-

Moureu,Chauvet

, p. 412 (1897)

-

Didecyldimethylammonium bromide (DDAB): a universal, robust, and highly potent phase-transfer catalyst for diverse organic transformations

Chidambaram, Mandan,Sonavane, Sachin U.,de la Zerda, Jaima,Sasson, Yoel

, p. 7696 - 7701 (2007)

Didecyldimethylammonium bromide (DDAB) has been scrutinized in comparison with traditional phase-transfer catalysts in variety of liquid-liquid reactions. It was found to be an exceptionally comprehensive, durable, and highly efficient phase-transfer catalyst (PTC) in a number of representative organic transformations such as C- and N-alkylations, isomerization, esterification, elimination, cyanation, bromination, and oxidation under very mild conditions of temperature and mixing. It was confirmed that DDAB is an exceedingly accessible and concurrently a highly liphophilic phase-transfer catalyst. This unprecedented characteristic renders DDAB to be a multipurpose catalyst that functions effectively both in mass transfer controlled and chemically controlled phase-transfer reactions.

Diastereomer-differentiating photochemistry of β-arylbutyrophenones: Yang cyclization versus type II elimination

Singhal, Nidhi,Koner, Apurba L.,Mal, Prasenjit,Venugopalan, Paloth,Nau, Werner M.,Moorthy, Jarugu Narasimha

, p. 14375 - 14382 (2005)

The diastereomers of ketones 2 and 3 are shown to exhibit distinct photochemical reactivities due to conformational preferences; while the anti isomers of 2 and 3 undergo efficient Yang cyclization in 75-90% yields with a remarkable diastereoselectivity (> 90%), the syn isomers predominantly undergo Norrish Type II elimination. The differences in the product profiles of the diastereomers are consistent with a mechanistic picture involving the formation of precursor diastereomeric triplet 1,4-biradicals in which the substituents at α and β-positions stabilize the cisoid (cyclization) or transoid (elimination) geometry. The fact that such a diastereomeric relationship does indeed ensue at the triplet-excited-state itself is demonstrated via the nanosecond laser-flash photolysis of model ketones 1. The diastereomeric discrimination in the product profiles observed for ketones 2 and 3 as well as in the triplet lifetimes observed for ketones 1 can both be mechanistically traced back to different conformational preferences of the ground-state diastereomeric ketones and the intermediary 1,4-biradicals. Additionally, it emerges from the present study that the syn and anti diastereomers of ketones 2 and 3 represent two extremes of a broad range of widely examined butyrophenones, which lead to varying degrees of Yang photocyclization depending on the alkyl substitution pattern.

Synthesis, characterization and in vitro biological evaluation of [Ru(η6-arene)(N,N)Cl]PF6 compounds using the natural products arenes methylisoeugenol and anethole

Delgado, Ricardo A.,Galdámez, Antonio,Villena, Joan,Reveco, Patricio G.,Thomet, Franz A.

, p. 131 - 137 (2015)

Abstract Five new organometallic Ru(II) compounds (VI-X) with the general formula [Ru(η6-arene)(N,N)Cl]PF6, where arene-N,N correspond to methylisoeugenol-bipyridine (VI); anethole-bipyridine (VII); methylisoeugenol-ethylenediamine (VIII); anethole-ethylenediamine (IX) and methylisoeugenol-1,2-diaminobenzene (X), have been synthesized, fully characterized and biologically evaluated in vitro. The reaction conditions based on the reduction of [Ru(1,5-COD)Cl2]n in situ with methyleugenol and estragole, which are natural ligands, induced an alkene isomerization on the allylic substituent of coordinated arenes. The Ru(II)-arene bond formation and isomerization of the CC bond on the allyl substituent was confirmed using 1H NMR spectroscopy; this result was validated for compound VIII by X-ray diffraction. An XRD analysis revealed the presence of both enantiomers of the complex in the single-crystal. Compounds IX and X exhibited a better cytotoxic activity in vitro than carboplatin, which is a commercial drug, against three human tumor cell lines (MCF-7, PC-3 and HT-29).

Phospholes as efficient ancillaries for the rhodium-catalyzed hydroformylation and hydroaminomethylation of estragole

Oliveira, Kelley C.B.,Carvalho, Sabrina N.,Duarte, Matheus F.,Gusevskaya, Elena V.,Dos Santos, Eduardo N.,Karroumi, Jamal El,Gouygou, Maryse,Urrutigo?ty, Martine

, p. 10 - 16 (2015)

The hydroaminomethylation (HAM) of estragole, a bio-renewable starting material, with di-n-butylamine was studied for the first time resulting in three novel amines. The process consists of the alkene hydroformylation followed by the in situ reductive amination of primarily formed aldehydes. In order to control chemo- and regioselectivities, three classes of phosphorus(III) compounds were employed as ancillaries for rhodium(I) catalysts: phosphine, phosphites and phospholes. Phosphole-promoted systems have showed the best overall performance, being more selective in the hydrofomylation step than non-promoted or phosphite-promoted systems, as well as more efficient in the reductive amination step than the standard triphenylphosphine based system. It has been found that both the double bond isomerization (a concurrent reaction) and the enamine hydrogenation (the last step in the HAM process) are favored by less electron-donating ligands, with phospholes presenting an excellent compromise to ensure high chemoselectivity and reasonably fast formation of target amines.

-

Bohrmann,Younken Jr.

, p. 1415,1416 (1968)

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Isomerization during olefin metathesis: An assessment of potential catalyst culprits

Higman, Carolyn S.,Plais, Lucie,Fogg, Deryn E.

, p. 3548 - 3551 (2013)

Two ruthenium hydride complexes commonly proposed as agents of unintended isomerization during olefin metathesis are examined for their activity in isomerization of estragole, a representative allylbenzene. Neither proves kinetically competent to account for the levels of isomerization observed during cross-metathesis of estragole by the second-generation Grubbs catalyst. A structure-activity analysis of selected ruthenium hydride complexes indicates that higher isomerization activity correlates with a more electrophilic metal center. It wasn't me: Two Ru hydrides thought to trigger double-bond migration during olefin metathesis are examined for their isomerization activity. Neither can account for the high levels of undesired isomerization seen during self-metathesis of estragole, a model allylbenzene substrate. Higher activity is found to correlate with a less electron-rich Ru center. Copyright

Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups

Cook, Adam,MacLean, Haydn,St. Onge, Piers,Newman, Stephen G.

, p. 13337 - 13347 (2021/11/20)

We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.

Spicing up olefin cross metathesis with the renewables estragole and methyl sorbate

Ferreira, Leonildo A.,Silva, Josiane T.,Alves, Raissa G.,Oliveira, Kelley C.B.,dos Santos, Eduardo N.

, (2021/05/03)

Diene moieties conjugated to a carbonyl group are ubiquitous in nature and are present in compounds with relevant biological properties. Herein we investigate the cross metathesis (CM) of the renewable cross partners estragole and methyl sorbate (MeSo) to produce methyl 6-(4-methoxyphenyl)hexa-2,4-dienoate. By the judicious choice of the ruthenium-based metathesis catalysts, as well as the reaction conditions, it was possible to obtain good conversion and selectivity for the desired product in catalyst loadings as low as 50 ppm (0.005 mol%), with a minimal amount of solvent.

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