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cis-Anethol

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cis-Anethol

EINECS 203-205-5
CAS No. 104-46-1 Density 0.988 g/mL at 25 °C(lit.)
PSA 9.23000 LogP 2.72830
Solubility N/A 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 N/A 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;

Article Data 69

cis-Anethol Synthetic route

863775-00-2

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

75-16-1

methylmagnesium bromide

104-46-1

anethole

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

C16H22N2O

A

5519-42-6

3,4,5-Trimethylpyrazole

B

104-46-1

anethole

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

1-bromo-1-propene

699-19-4

4-methoxyphenylmagnesium chloride

104-46-1

anethole

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

ethyl 1-propenyl ether

13139-86-1

4-methoxyphenyl magnesium bromide

104-46-1

anethole

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

4-chloromethoxybenzene

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%
74568-53-9

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

A

140-67-0

Estragole

B

74568-54-0

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

C

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

ethyl p-methoxycinnamate

A

140-67-0

Estragole

B

53484-50-7, 17581-85-0

p-methoxycinnamyl alcohol

C

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

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%
104-92-7

1-bromo-4-methoxy-benzene

590-14-7

1-bromo-1-propene

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%
140-67-0

Estragole

A

87797-12-4

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

B

4705-34-4

4,4'-dimethoxystilbene

C

34414-53-4

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

D

104-46-1

anethole

E

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%

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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