METHYL 4-AMINOSALICYLATE Chemical Properties

Melting point:

120-123°C

Boiling point:

120 °C

Density 

1.305±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

9.81±0.10(Predicted)

form 

Powder

color 

White to Pale Beige

Water Solubility 

Slightly soluble in water.

λmax

254nm(lit.)

CAS DataBase Reference

4136-97-4(CAS DataBase Reference)

Safety Information

RTECS 

VO1683000

HazardClass 

IRRITANT

HS Code 

2922500090

METHYL 4-AMINOSALICYLATE Usage And Synthesis

Uses

Methyl 4-aminosalicylate is used as pharmaceutical intermediate.

Definition

ChEBI: P-Aminosalicylic acid methyl ester is an aromatic amine.

Synthesis

Step 2: Preparation of methyl 4-amino-2-hydroxybenzoate In a 500 mL Parr reactor, methyl 2-hydroxy-4-nitrobenzoate (1.3 g, 6.59 mmol) was mixed with a suspension formed by 10% Pd/C catalyst (100 mg) in methanol (40 mL). The reaction mixture was shaken for 1 h under hydrogen atmosphere (30 psi). Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. Methyl 4-amino-2-hydroxybenzoate was obtained as a yellow solid (1.08 g, 6.46 mmol, 98% yield). The product was analyzed by UPLC-MS showing 100% purity and the mass spectrum (MS/ESI+) showed a molecular ion peak [MH]+ of 167.9.

References

[1] ACS Catalysis, 2014, vol. 4, # 6, p. 1777 - 1782
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3597 - 3600
[3] Patent: US2014/155391, 2014, A1. Location in patent: Paragraph 0432; 0434
[4] Journal of the Chemical Society, 1949, p. 1498,1502
[5] Proceedings - Indian Academy of Sciences, Section A, 1950, vol. 32, p. 357,362

METHYL 4-AMINOSALICYLATE(4136-97-4)Related Product Information

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• Methyl-4-amino-3-bromo-5-methylbenzoate
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• METHYL PENTAFLUOROBENZOATE
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• METHYL 3-(4-METHOXYPHENYL)PROPIONATE
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