METHYL 3,5-DIHYDROXYBENZOATE Chemical Properties

Melting point:

67-70 °C (lit.)

Boiling point:

253.6±20.0 °C(Predicted)

Density 

1.354±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Acetone (Slightly), Methanol (Slightly)

form 

Solid

pka

9.24±0.10(Predicted)

color 

Light Brown

InChI

InChI=1S/C8H8O4/c1-12-8(11)7-5(9)3-2-4-6(7)10/h2-4,9-10H,1H3

InChIKey

WCQZCKUNZVMBDC-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=C(O)C=CC=C1O

LogP

2.290 (est)

CAS DataBase Reference

2150-45-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29182900

MSDS

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

METHYL 3,5-DIHYDROXYBENZOATE Usage And Synthesis

Uses

Methyl 2,6-dihydroxybenzoate may be used for the preparation of methyl 2-hydroxy-6-methoxybenzoate and oxamyl propionic acid.

Definition

ChEBI: Methyl 2,6-dihydroxybenzoate is a member of phenols and a benzoate ester. It is functionally related to a salicylic acid.

General Description

Methyl 2,6-dihydroxybenzoate can be synthesized from 2,6-dihydroxybenzoic acid. Multiple fluorescences in methyl 2,6-dihydroxybenzoate have been investigated. Its short wavelength (387) and long wavelength (500) emissions are reported to arise from extramolecularly hydrogen-bonded and intramolecularly hydrogen-bonded species.

Synthesis

The general procedure for the synthesis of methyl 2,6-dihydroxybenzoate from 2,6-dihydroxybenzoic acid is as follows: a) 80% sodium hydride (10.00 g, 333.3 mmol) was dissolved in N,N-dimethylformamide (45 mL) under argon protection and the solution was cooled to 0°C. Subsequently, a solution of 2,6-dihydroxybenzoic acid (48.88 g, 317.1 mmol) in N,N-dimethylformamide (50 mL) was slowly added over 45 minutes. After stirring for 45 minutes, iodomethane (21.0 mL, 337 mmol) was added dropwise over 20 minutes. The reaction mixture was stirred at room temperature for 70 hours. Upon completion of the reaction, the mixture was diluted with dichloromethane and filtered through a silica gel plug, using dichloromethane as the eluent. Finally, the solvent was evaporated to afford the target product methyl 2,6-dihydroxybenzoate (35.22 g, 66.1% yield). The product was characterized by 1H NMR (250 MHz, DMSO-d6): δ 9.91 (s, 2H), 7.09 (t, J = 1.2 Hz, J = 2.5 Hz, 1H), 6.37 (d, J = 1.1 Hz, 2H), 3.78 (s, 3H).

References

[1] Patent: US6204294, 2001, B1
[2] Patent: US4663344, 1987, A
[3] Patent: US6200981, 2001, B1

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