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122-84-9

Basic Information
CAS No.: 122-84-9
Name: 4-Methoxyphenylacetone
Article Data: 151
Molecular Structure:
Molecular Structure of 122-84-9 (4-Methoxyphenylacetone)
Formula: C10H12O2
Molecular Weight: 164.204
Synonyms: 2-Propanone,(p-methoxyphenyl)- (6CI,7CI);2-Propanone, 1-(p-methoxyphenyl)- (8CI);1-(4-Methoxyphenyl)-2-propanone;1-(4-Methoxyphenyl)acetone;1-(p-Anisyl)-2-propanone;1-(p-Methoxyphenyl)-2-propanone;4-Methoxybenzylmethyl ketone;4'-Methoxyphenyl-2-propanone;Anisketone;Anisyl methyl ketone;NSC 22983;NSC 46101;p-Acetonylanisole;p-Methoxybenzyl methyl ketone;p-Methoxyphenylacetone;
EINECS: 204-578-7
Density: 1.027 g/cm3
Melting Point: <-15 °C
Boiling Point: 268 °C at 760 mmHg
Flash Point: 101.7 °C
Solubility: 3.084g/L at 25℃
Appearance: pale yellow liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 23-24/25
PSA: 26.30000
LogP: 1.82670
Synthetic route
696-62-8

para-iodoanisole

67-64-1

acetone

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; caesium carbonate at 90℃; for 16h; Inert atmosphere; sealed vial;98%
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; [Pd(π-cinnamyl)Cl]2; caesium carbonate at 25℃; for 48h; Sealed tube; Inert atmosphere; Glovebox;76%
98815-48-6

1-bromo-2-(4-methoxyphenyl)propan-2-ol

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With diethylzinc In dichloromethane at 20℃; for 2h;95%
1712-69-2

1-isopropenyl-4-methoxybenzene

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With [hydroxy(tosyloxy)iodo]benzene In methanol at 20℃; for 0.333333h;92%
With oxone; sodium iodide In water; acetonitrile at 20℃; for 15h; Green chemistry;85%
Stage #1: 1-isopropenyl-4-methoxybenzene With 2-Iodo-5-methylbenzenesulfonic acid In tert-butyl methyl ether; water; isopropyl alcohol at 22℃; for 0.0833333h; Inert atmosphere;
Stage #2: With Oxone In tert-butyl methyl ether; water; isopropyl alcohol at 22℃; for 4h; Inert atmosphere; Further stages;
68%
With iodine; mercury(II) oxide Man laesst auf das entstandene Jodhydrin AgNO3 oder HgO einwirken;
140-67-0

Estragole

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With iron(III) chloride; palladium(II) trifluoroacetate; sodium 2,2,2-trifluoroacetate In water; acetonitrile at 30℃; Temperature; Wacker-Tsuji Olefin Oxidation; Inert atmosphere; Darkness;92%
Multi-step reaction with 2 steps
1: yellow HgO; absolute methanol; iodine
2: alcoholic potash / Durch Einw. von 20prozentiger Schwefelsaeure das Reaktionsprodukt
View Scheme
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
2: Rh((1,8-bis(imidazolin-2-ylidene)-3,6-di(tert-butyl)carbazolide)homoallyl) / benzene-d6 / 2 h / 20 °C / Inert atmosphere; Schlenk technique
View Scheme

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

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With SO3H silica gel In methanol at 50℃; for 2h; Inert atmosphere;92%
98236-12-5

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

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;90%
94169-18-3

1-(4-Methoxy-phenyl)-propan-2-one O-methyl-oxime

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With hydrogenchloride In methanol at 65℃; for 10h;90%
696-62-8

para-iodoanisole

123-54-6

acetylacetone

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With copper(l) iodide; potassium phosphate tribasic trihydrate In dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere;89%
65739-10-8

1-(4-methoxyphenyl)-2-methyl-3-phenylpropan-2-ol

A

122-84-9

4-methoxybenzyl methyl ketone

B

103-79-7

1-phenyl-acetone

Conditions
ConditionsYield
With 2,3,5-trimethyl-pyridine; [Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridyl)](PF6); thiophenol In dichloromethane at 20℃; Sealed tube; Inert atmosphere; Irradiation;A 5%
B 89%
623-12-1

4-chloromethoxybenzene

67-64-1

acetone

122-84-9

4-methoxybenzyl methyl ketone

Conditions
ConditionsYield
With potassium phosphate; 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate at 90℃; for 18h; Inert atmosphere; Schlenk technique;88%
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 2-methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine; caesium carbonate at 90℃; for 24h; Kinetics; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube;84%
With 2-methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine; palladium cinnamyl chloride; caesium carbonate at 90℃; for 12h; Schlenk technique; Inert atmosphere;84%
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Consensus Reports

ANISIC KETONE(122-84-9) is reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

The IUPAC name of Anisic ketone is 1-(4-methoxyphenyl)propan-2-one. With the CAS registry number 122-84-9, it is also named as 4-Methoxyphenylacetone. The product's categories are Aromatic Ketones (substituted); API Intermediates; Aromatics; Miscellaneous Reagents. Besides, it is pale yellow liquid, which should be stored in ventilated, dry place. In addition, its molecular formula is C10H12O2 and molecular weight is 164.20.

The other characteristics of this product can be summarized as: (1)EINECS: 204-578-7; (2)ACD/LogP: 1.35; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.35; (5)ACD/LogD (pH 7.4): 1.35; (6)#H bond acceptors: 2; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 3; (9)Polar Surface Area: 26.3 Å2; (10)Index of Refraction: 1.501; (11)Molar Refractivity: 47.14 cm3; (12)Molar Volume: 159.8 cm3; (13)Polarizability: 18.68×10-24cm3; (14)Surface Tension: 33.7 dyne/cm; (15)Density: 1.027 g/cm3; (16)Flash Point: 101.7 °C; (17)Melting Point: <-15 °C; (18)Enthalpy of Vaporization: 50.61 kJ/mol; (19)Boiling Point: 268 °C at 760 mmHg; (20)Vapour Pressure: 0.00789 mmHg at 25 °C.

Preparation of Anisic ketone: this chemical can be prepared by 1-(2-Iodo-1-methoxy-1-methyl-ethyl)-4-methoxy-benzene.



This reaction needs m-Chloroperbenzoic acid and CH2Cl2 at temperature of 0 °C. The reaction time is 1 hour. The yield is 90 %.

Uses of Anisic ketone: this chemical is used as pharmaceutical intermediate. Similarly, it can react with Benzylamine to get Benzyl-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-amine.



This reaction needs H2, Pt-C and Ethanol. The yield is 99 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. Please do not breathe vapour. And you should avoid contact with skin and eyes.

People can use the following data to convert to the molecule structure.
(1)SMILES: COc1ccc(CC(C)=O)cc1
(2)InChI: InChI=1/C10H12O2/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6H,7H2,1-2H3
(3)InChIKey: WFWKNGZODAOLEO-UHFFFAOYAM
(4)Std. InChI: InChI=1S/C10H12O2/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6H,7H2,1-2H3
(5)Std. InChIKey: WFWKNGZODAOLEO-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 560mg/kg (560mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: TREMOR

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Journal of Pharmaceutical Sciences. Vol. 60, Pg. 799, 1971.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 857, 1979.
rat LD50 oral 3330mg/kg (3330mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: TREMOR

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Food and Cosmetics Toxicology. Vol. 17, Pg. 857, 1979.