4-Amino-2-methylbenzoic acid Chemical Properties

Melting point:

160-165 °C

Boiling point:

339.5±30.0 °C(Predicted)

Density 

1.254±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

Solid

pka

4.86±0.25(Predicted)

color 

Light orange to Yellow to Green

InChI

InChI=1S/C8H9NO2/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4H,9H2,1H3,(H,10,11)

InChIKey

XRSQZFJLEPBPOZ-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(N)C=C1C

CAS DataBase Reference

2486-75-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26

WGK Germany 

3

HS Code 

29224999

4-Amino-2-methylbenzoic acid Usage And Synthesis

Chemical Properties

White powder

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

GENERAL STEPS: Prior to each experiment, the tubular reaction apparatus was equilibrated by pumping solvent for 30 min at 16 bar hydrogen pressure (see Fig. 4). An Omnifit reaction cartridge (20.0 mm outer diameter, 15.0 mm inner diameter) containing 1 g Pd/C catalyst was used. To prevent overpressurization of the system in case of blockage, the upper pressure of the Knauer pump was set to 25 bar. with the injection ring disconnected from the flow line, the injection ring was opened and manually injected with 3.6 mL of a 0.076 M ethanol solution of 2-methyl-4-nitrobenzoic acid (excess feedstock solution in the ring was recovered for reuse). The injection ring was then closed and plugged into the flow stream. Collect the product at the outlet of the system downstream of the backpressure regulator for 120 min. The solvent is removed by reduced pressure distillation (first using a rotary evaporator and then a secondary rotary vane pump) to give 4-amino-2-methylbenzoic acid.

References

[1] Tetrahedron, 2018, vol. 74, # 47, p. 6795 - 6803
[2] Chemische Berichte, 1884, vol. 17, p. 161
[3] Patent: US2012/46467, 2012, A1. Location in patent: Page/Page column 26

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