Methyl 4-methoxysalicylate Chemical Properties

Melting point:

50-53 °C (lit.)

Boiling point:

134°C 7mm

Density 

1.1634 (rough estimate)

refractive index 

1.4600 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystalline Powder or Crystals

pka

9.38±0.10(Predicted)

color 

White to light yellow

Water Solubility 

Soluble in acetone. Insoluble in water.

BRN 

2691644

InChIKey

ZICRWXFGZCVTBZ-UHFFFAOYSA-N

LogP

2.430 (est)

CAS DataBase Reference

5446-02-6(CAS DataBase Reference)

NIST Chemistry Reference

Methyl 4-methoxysalicylate(5446-02-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29189900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl 4-methoxysalicylate Usage And Synthesis

Chemical Properties

white to light yellow crystalline powder

Uses

Methyl 4-methoxysalicylate (methyl 2-hydroxy-4-methoxybenzoate) was used in the enantioselective synthesis of (+)-coriandrone A and B, two bioactive natural products.

Synthesis

General procedure for the synthesis of methyl 4-methoxysalicylate from methyl 4-methoxybenzoate: Ru(MesCO2)(L) (p-cymene) [L=2,2'-bipyridine or 4,4'-dibromo bipyridine] (2.5 mol%), oxidizing agent (2.0 eq.), and methyl 4-methoxybenzoate (1.0 eq.) were added to a sealed tube. Subsequently, a mixture of trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA) in the ratio of 0.6 mL:0.4 was added. The reaction mixture was placed in an oil bath preheated to 110 °C and stirred until the reaction was complete, and the reaction process was continuously monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was quenched by the addition of ice water and extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate (Na2SO4) and subsequently concentrated by rotary evaporator. Finally, the residue was purified by silica gel column chromatography to afford the target product methyl 4-methoxysalicylate.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 38, p. 3743 - 3746

Methyl 4-methoxysalicylate(5446-02-6)Related Product Information

• (Trifluoromethoxy)benzene
• 4-Methoxyphenylacetic acid
• METHYL THIOPHENE-2-CARBOXYLATE
• ACETYLSALICYLIC ACID METHYL ESTER
• Anisole
• Methyl acrylate
• Methyl salicylate
• 4-Methoxybenzylchloride
• p-Anisaldehyde
• 2'-Hydroxy-3-phenylpropiophenone
• 4-Methoxybenzoic acid
• Kresoxim-methyl
• CHLOROPHOSPHONAZO III
• Bensulfuron methyl
• Methylparaben
• Butylparaben
• Methyl acetate
• Thiophanate-methyl