Product Name

  • Name

    4-Methoxycinnamic acid

  • EINECS 212-594-0
  • CAS No. 830-09-1
  • Article Data190
  • CAS DataBase
  • Density 1.195 g/cm3
  • Solubility
  • 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
  • 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;
  • PSA 46.53000
  • LogP 1.79300

Synthetic route

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

acrylic acid
79-10-7

acrylic acid

3-(4'-methoxyphenyl)propenoic 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%
methyl p-methoxycinnamate
832-01-9, 3901-07-3, 19310-29-3

methyl p-methoxycinnamate

3-(4'-methoxyphenyl)propenoic acid
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;
malonic acid
141-82-2

malonic acid

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3-(4'-methoxyphenyl)propenoic acid
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%
para-iodoanisole
696-62-8

para-iodoanisole

acrylic acid
79-10-7

acrylic acid

3-(4'-methoxyphenyl)propenoic 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%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3-(4'-methoxyphenyl)propenoic acid
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%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

3-(4'-methoxyphenyl)propenoic acid
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%
acetic anhydride
108-24-7

acetic anhydride

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3-(4'-methoxyphenyl)propenoic acid
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
Methyl 2-iodo-3-(4-methoxyphenyl)propionate
110621-98-2

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

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol for 3h; Heating;89%
(C6H4OCH3)CHCH(BO2C5H10)
905966-49-6

(C6H4OCH3)CHCH(BO2C5H10)

carbon dioxide
124-38-9

carbon dioxide

3-(4'-methoxyphenyl)propenoic acid
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%
ethyl p-methoxycinnamate
24393-56-4, 51507-22-3, 1929-30-2

ethyl p-methoxycinnamate

3-(4'-methoxyphenyl)propenoic acid
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%
para-iodoanisole
696-62-8

para-iodoanisole

ethyl acrylate
140-88-5

ethyl acrylate

A

ethyl p-methoxycinnamate
24393-56-4, 51507-22-3, 1929-30-2

ethyl p-methoxycinnamate

B

methoxybenzene
100-66-3

methoxybenzene

C

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide at 90℃; for 5h; Solvent; Sealed tube;A 66%
B 16%
C 19%
With potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 5h; Solvent; Reagent/catalyst; Sealed tube;A 26%
B 22%
C 31%
...Expand
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

acetic acid
64-19-7

acetic acid

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
Stage #1: acetic acid With sodium tetrahydroborate at 20 - 100℃; for 2h;
Stage #2: 4-methoxy-benzaldehyde In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 12h;		59%
Stage #1: acetic acid With sodium tetrahydroborate at 10 - 100℃; for 1.5h;
Stage #2: 4-methoxy-benzaldehyde In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 10h; Knoevenagel Condensation; Reflux;		55%
zinc diacetate
557-34-6

zinc diacetate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With acetic acid In 1-methyl-pyrrolidin-2-one at 185 - 195℃;58%
acrylic acid
79-10-7

acrylic acid

bis(4-methoxyphenyl)iodonium tetrafluoroborate

bis(4-methoxyphenyl)iodonium tetrafluoroborate

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate In water at 100℃; for 3h;50%
acrylic acid
79-10-7

acrylic acid

Bis-(4-methoxy-phenyl)-iodonium; hydrogen sulfate

Bis-(4-methoxy-phenyl)-iodonium; hydrogen sulfate

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate In water at 100℃; for 3h;50%
para-iodoanisole
696-62-8

para-iodoanisole

ethyl acrylate
140-88-5

ethyl acrylate

A

ethyl p-methoxycinnamate
24393-56-4, 51507-22-3, 1929-30-2

ethyl p-methoxycinnamate

B

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 5h; Reagent/catalyst; Sealed tube; regioselective reaction;A 35%
B 28%
...Expand
para-iodoanisole
696-62-8

para-iodoanisole

ethyl acrylate
140-88-5

ethyl acrylate

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With sodium acetate In water at 90℃; for 5h; Sealed tube; regioselective reaction;16%
4-methoxycinnamic acid amide
36650-51-8, 18166-63-7

4-methoxycinnamic acid amide

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol; water for 4h; Reflux;12%
4-Methoxystyrene
637-69-4

4-Methoxystyrene

CO2 trapped single chain Lewis acid pair polymer nanoparticles

CO2 trapped single chain Lewis acid pair polymer nanoparticles

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
at 25℃; under 0.750075 - 75.0075 Torr; for 4h; Schlenk technique;6%
4-methoxycinnamaldehyde
1963-36-6

4-methoxycinnamaldehyde

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With silver(l) oxide
malonic acid
141-82-2

malonic acid

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

A

3-amino-3-(4-methoxyphenyl)propionic acid
5678-45-5

3-amino-3-(4-methoxyphenyl)propionic acid

B

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With ammonia
...Expand
›Tyr
556-02-5, 556-03-6, 34537-57-0, 55520-40-6, 96946-98-4, 60-18-4

›Tyr

methyl iodide
74-88-4

methyl iodide

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With methanol; potassium carbonate
malonic acid
141-82-2

malonic acid

p-methoxybenzylidene-phenylamine
836-41-9

p-methoxybenzylidene-phenylamine

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With ethanol
4-(4-methoxyphenyl)-3-buten-2-one
3815-30-3

4-(4-methoxyphenyl)-3-buten-2-one

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With sodium hypochlorite
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

methyl iodide
74-88-4

methyl iodide

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With methanol; potassium hydroxide Verseifen des entstandenen Methylesters mit Alkali;
With methanol; potassium hydroxide at 140℃; im geschlossenen Rohr; Verseifen des entstandenen Methylesters mit Alkali;
(2RS,3SR)-2,3-dibromo-3-(4-methoxyphenyl)propanoic acid
31448-61-0, 77820-32-7

(2RS,3SR)-2,3-dibromo-3-(4-methoxyphenyl)propanoic acid

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With sodium iodide In 2-methoxy-ethanol at 49.9℃; for 168h; Kinetics; Mechanism; Thermodynamic data; in dark; ΔH(excit.), ΔS(excit.), ΔG(excit.); other temperatures;
tetrachloromethane
56-23-5

tetrachloromethane

4-Methoxystyrene
637-69-4

4-Methoxystyrene

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

Conditions
ConditionsYield
With water; toluene-4-sulfonic acid; acetic acid; copper(l) chloride 1.) reflux, 3.5 h, 2.) reflux, 1.5 h; Yield given. Multistep reaction;
2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-methoxyphenyl)-propionic acid
52913-16-3

2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-methoxyphenyl)-propionic acid

A

phthalimide
136918-14-4

phthalimide

B

3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

C

(S)-4-(4-Methoxy-phenyl)-1,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[c]azepine-3-carboxylic acid

(S)-4-(4-Methoxy-phenyl)-1,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[c]azepine-3-carboxylic acid

Conditions
ConditionsYield
In acetone at 20℃; for 24h; Irradiation; Yield given. Yields of byproduct given;
...Expand

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.

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View