3,4-Dimethoxycinnamic acid Chemical Properties

Melting point:

181-183 °C(lit.)

Boiling point:

267.4°C (rough estimate)

Density 

1.0627 (rough estimate)

refractive index 

1.4389 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Solubility in hot methanol, very faint turbidity. Soluble in dichloromethane, chloroform.

form 

Powder

pka

4.53±0.10(Predicted)

color 

Slightly yellow to light beige

BRN 

1533435

InChI

InChI=1S/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3,(H,12,13)

InChIKey

HJBWJAPEBGSQPR-GQCTYLIASA-N

SMILES

C(O)(=O)C=CC1=CC=C(OC)C(OC)=C1

LogP

2.340

CAS DataBase Reference

2316-26-9(CAS DataBase Reference)

NIST Chemistry Reference

3,4-Dimethoxycinnamic acid(2316-26-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29189900

MSDS

• Language:English Provider:Caffeic acid dimethyl ether
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,4-Dimethoxycinnamic acid Usage And Synthesis

Chemical Properties

Slightly yellow to light beige powder

Uses

3,4-Dimethoxycinnamic Acid is a Cinnamic Acid (C442030) derivative,used in the synthesis of amides and esters through coupling reactions involving carboxylic acids and amines and N-methylation of amides and O-methylation of carboxylic acids.

Definition

ChEBI: 3,4-dimethoxycinnamic acid is a methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively. It is functionally related to a trans-cinnamic acid.

Synthesis

GENERAL METHOD: In a dry reaction vessel, veratraldehyde (500 mg, 1.0 eq.) and malonic acid (981 mg, 2.0 eq.) were dissolved in dimethylformamide (5 mL), followed by the addition of DABCO (105 mg, 0.2 eq.). The reaction mixture was stirred at 100-110°C for 60-90 min. The reaction progress was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was slowly poured into ice water and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by recrystallization from a chloroform/hexane solvent mixture to afford 3,4-dimethoxycinnamic acid in good yield.

References

[1] Organic Letters, 2016, vol. 18, # 5, p. 1182 - 1185
[2] Oriental Journal of Chemistry, 2012, vol. 28, # 4, p. 1725 - 1728
[3] Asian Journal of Chemistry, 2017, vol. 29, # 7, p. 1561 - 1564
[4] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 6, p. 1589 - 1594
[5] RSC Advances, 2015, vol. 5, # 34, p. 26596 - 26603

3,4-Dimethoxycinnamic acid(2316-26-9)Related Product Information

• 3,4-Dimethoxyphenol
• Diphenyldimethoxysilane
• Dacthal
• Ethyl 4-methoxycinnamate
• Dimethyl ether
• Dimethyldimethoxysilane
• Dimethyl phthalate
• Dimethyl sulfate
• Dimethyl carbonate
• 1,3-Dimethoxybenzene
• ETHANE
• 4-Hydroxycinnamic acid
• 1,1-Dimethoxyethane
• 3,4,5-Trimethoxycinnamic acid
• N,N-Dimethylformamide
• Octyl 4-methoxycinnamate
• Dimethoxymethane
• 4-Methoxycinnamic acid