Methyl 4-amino-3-methylbenzoate Chemical Properties

Melting point:

116 °C

Boiling point:

314.8±22.0 °C(Predicted)

Density 

1.132±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO, Methanol

form 

Solid

pka

2.32±0.10(Predicted)

color 

Light Beige

CAS DataBase Reference

18595-14-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-37/38-36-22

Safety Statements 

26-37/39

HazardClass 

IRRITANT

HS Code 

2922498590

Methyl 4-amino-3-methylbenzoate Usage And Synthesis

Chemical Properties

White to light yellow crystal powder

Uses

Methyl 4-Amino-3-methylbenzoate is used in the synthesis of neuroprotective hydrazides used in the treatment of Alzheimer’s. It is also used in the research and development of diphenylamine-based retinoids.

Synthesis

The general procedure for the synthesis of methyl 4-amino-3-methylbenzoate from methyl 3-methyl-4-nitrobenzoate was as follows: methyl 3-methyl-4-nitrobenzoate (50 g, 256.2 mmol) was dissolved in methanol (1.5 L), and palladium carbon catalyst (2.5 g) was added. Hydrogen (H2) was passed into the reaction mixture at room temperature and the reaction was continuously stirred overnight. Upon completion of the reaction, the solid catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford the light yellow solid product methyl 4-amino-3-methylbenzoate (38 g, 90% yield). The product was analyzed by LCMS (electrospray ionization, positive ion mode) with a mass-to-charge ratio (m/z) of 166.1, corresponding to the [M + H]+ ion peak.

References

[1] Tetrahedron, 2018, vol. 74, # 47, p. 6795 - 6803
[2] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4582 - 4589
[4] Patent: WO2014/66795, 2014, A1. Location in patent: Paragraph 0175
[5] Zeitschrift fur Anorganische und Allgemeine Chemie, 2014, vol. 640, # 1, p. 159 - 167

Methyl 4-amino-3-methylbenzoate(18595-14-7)Related Product Information

• 4-Dimethylaminobenzoic acid
• 4-Aminobenzoic acid
• 4-Methyl-3-nitrobenzoic acid methyl ester
• Methyl benzoate
• 4-Amino-3-methylphenol
• Methyl acrylate
• Bensulfuron methyl
• Methylparaben
• METSULFURON METHYL
• Methyl acetate
• Methyl 4-aminobenzoate
• 3-Methylanthranilic acid
• Methyl 2-iodobenzoate
• Kresoxim-methyl
• Thiophanate-methyl
• Methyl
• Methyl 3-amino-4-methylbenzoate 98%,METHYL 3-AMINO-4-METHYLBENZOATE
• Methyl4-amino-2-methylbenzoate