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4-Methoxycinnamic acid

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Name

4-Methoxycinnamic acid

EINECS 212-594-0
CAS No. 830-09-1 Density 1.195 g/cm3
PSA 46.53000 LogP 1.79300
Solubility N/A Melting Point 173-175 °C
Formula C10H10O3 Boiling Point 342.6 °C at 760 mmHg
Molecular Weight 178.188 Flash Point 138.6 °C
Transport Information N/A Appearance white fine crystalline powder
Safety 26-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 830-09-1 (4-Methoxycinnamic acid) Hazard Symbols IrritantXi
Synonyms

Cinnamicacid, p-methoxy- (6CI,8CI);3-(4-Methoxyphenyl)-2-propenoic acid;3-(4-Methoxyphenyl)acrylic acid;3-(4-Methoxyphenyl)propenoic acid;4-Methoxycinnamic acid;4'-Methoxycinnamic acid;Bernel hydro;NSC 5303;NSC623437;O-Methyl-p-coumaric acid;p-Methoxycinnamic acid;3-(4-methoxyphenyl)prop-2-enoic acid;2-propenoic acid, 3-(4-methoxyphenyl)-;3-(4-methoxyphenyl)acrylic acid;

Article Data 190

4-Methoxycinnamic acid Synthetic route

104-92-7

1-bromo-4-methoxy-benzene

79-10-7

acrylic acid

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With potassium carbonate; palladium diacetate; tris-(o-tolyl)phosphine In N,N,N,N,N,N-hexamethylphosphoric triamide; water at 100℃; for 1.5h;98%
With tetrabutylammomium bromide; sodium carbonate In water at 90℃; for 22h; Heck Reaction; Green chemistry;90%
Stage #1: acrylic acid With sodium carbonate In water
Stage #2: With copper (II) carbonate hydroxide In water for 0.166667h; Autoclave;
Stage #3: 1-bromo-4-methoxy-benzene Reagent/catalyst; Further stages;
88.1%
832-01-9, 3901-07-3, 19310-29-3

methyl p-methoxycinnamate

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With iron(III) sulfate; water In toluene at 110℃; for 2h; Ionic liquid;98%
With sodium hydroxide In tetrahydrofuran; ethanol; water at 20℃; for 12h;
141-82-2

malonic acid

123-11-5

4-methoxy-benzaldehyde

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With piperidine In pyridine at 100 - 120℃; for 2.25h;97.4%
With piperidine; pyridine at 80℃; for 7h;97.5%
With piperidine; pyridine at 75℃; for 7h; Perkin Carboxylic Acid Synthesis;97.5%
696-62-8

para-iodoanisole

79-10-7

acrylic acid

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With tributyl-amine In N,N-dimethyl-formamide at 90℃; for 7h; Heck Reaction; Reflux;97%
With potassium hydroxide In water at 90℃; for 5h; Mizoroki-Heck reaction;96%
Stage #1: acrylic acid With potassium tert-butylate In water at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: para-iodoanisole With C16H21Br2N3Pd In water at 100℃; for 24h; Mizoroki-Heck reaction; Inert atmosphere; Sealed tube;
95%
2033-24-1

cycl-isopropylidene malonate

123-11-5

4-methoxy-benzaldehyde

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With 2-carbamoylhydrazine-1-sulfonic acid In neat (no solvent) at 110℃; for 0.416667h; Reagent/catalyst; Green chemistry;96%
104-92-7

1-bromo-4-methoxy-benzene

292638-85-8

acrylic acid methyl ester

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate; palladium In water at 170℃; for 0.25h; Heck Reaction; Microwave irradiation;93%
With tetrabutylammomium bromide; potassium carbonate In water at 170℃; for 0.333333h; Heck Reaction; Microwave irradiation;93%
108-24-7

acetic anhydride

123-11-5

4-methoxy-benzaldehyde

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With zinc diacetate; potassium acetate In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; Catalytic behavior; Temperature; Reagent/catalyst; Reflux; Large scale;92.5%
With sodium tetramethoxyborate; lithium chloride In 1-methyl-pyrrolidin-2-one for 12h; Perkin reaction; Heating;59%
With sodium acetate at 175 - 180℃; im geschlossenen Rohr;
With sodium acetate at 170℃; im geschlossenen Rohr;
With sodium acetate
110621-98-2

Methyl 2-iodo-3-(4-methoxyphenyl)propionate

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol for 3h; Heating;89%
905966-49-6

(C6H4OCH3)CHCH(BO2C5H10)

124-38-9

carbon dioxide

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;89%
24393-56-4, 51507-22-3, 1929-30-2

ethyl p-methoxycinnamate

830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 20℃; for 24h;75%
Stage #1: ethyl p-methoxycinnamate With sodium hydroxide In ethanol
Stage #2: With hydrogenchloride In water
64%

4-Methoxycinnamic acid Specification

The p-Methoxycinnamic acid, with the CAS registry number 830-09-1 and EINECS registry number 213-405-4, has the systematic name of 3-(4-methoxyphenyl)prop-2-enoic acid. And the molecular formula of this chemical is C10H10O3. It is a kind of white fine crystalline powder, and belongs to the classification code of Drug/Therapeutic Agent. What's more, it is often used in the cosmetics, and it is also used as medicine intermediate to produce esmolol.

The physical properties of p-Methoxycinnamic acid are as following: (1)ACD/LogP: 2.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.89; (4)ACD/LogD (pH 7.4): -0.85; (5)ACD/BCF (pH 5.5): 1.23; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 15.45; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 35.53 Å2; (13)Index of Refraction: 1.591; (14)Molar Refractivity: 50.38 cm3; (15)Molar Volume: 149 cm3; (16)Polarizability: 19.97×10-24cm3; (17)Surface Tension: 46.2 dyne/cm; (18)Density: 1.195 g/cm3; (19)Flash Point: 138.6 °C; (20)Enthalpy of Vaporization: 61.88 kJ/mol; (21)Boiling Point: 342.6 °C at 760 mmHg; (22)Vapour Pressure: 2.86E-05 mmHg at 25°C.

Preparation of p-Methoxycinnamic acid: This chemical can be prepared by acetic acid anhydride and 4-methoxy-benzaldehyde. The reaction will need reagent sodium tetramethoxyborate and LiCl, and the solvent 1-methyl-pyrrolidin-2-one. The reaction time is 12 hours with heating, and the yield is about 59%. 

p-Methoxycinnamic acid can be prepared by acetic acid anhydride and 4-methoxy-benzaldehyde

Uses of p-Methoxycinnamic acid: It can react with methyllithium to produce 4t-(4-methoxy-phenyl)-but-3-en-2-one. This reaction will need the solvent diethyl ether. The reaction temperature is 5-20 hours, and the yield is about 62.5%.

p-Methoxycinnamic acid can react with methyllithium to produce 4t-(4-methoxy-phenyl)-but-3-en-2-one. This reaction will need the solvent diethyl ether

 

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C=Cc1ccc(OC)cc1
(2)InChI: InChI=1/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)
(3)InChIKey: AFDXODALSZRGIH-UHFFFAOYAN

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intraperitoneal > 1300mg/kg (1300mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: REGIDITY
Indian Journal of Pharmaceutical Sciences. Vol. 49, Pg. 77, 1987.

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