Methyl 2,3-diaminobenzoate Chemical Properties

Melting point:

68-70°C

Boiling point:

322.6±22.0 °C(Predicted)

Density 

1.260±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

3.02±0.10(Predicted)

form 

powder to crystal

color 

Light yellow to Brown

InChI

InChI=1S/C8H10N2O2/c1-12-8(11)5-3-2-4-6(9)7(5)10/h2-4H,9-10H2,1H3

InChIKey

BLJHLOLVEXWHFS-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC(N)=C1N

CAS DataBase Reference

107582-20-7(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38-43

Safety Statements 

26-36/37/39-36/37

HS Code 

2921599090

Methyl 2,3-diaminobenzoate Usage And Synthesis

Application

2,3-Diaminobenzoate is a pharmaceutical intermediate that can be used to prepare methyl 2-ethoxy-4-carboxylate-3-hydro-benzimidazole, which in turn can be used to prepare triphenylmethylcandesartan intermediate.

Chemical Properties

Yellow Solid

Anticancer Research

2,3-Diaminobenzoic acid methyl ester is a redox potential catalyst that has been shown to have anticancer activity in vitro and in vivo. It is a 5-ht4 receptor agonist, which causes an increase in the intracellular concentration of cAMP. The anticancer effect of this compound may be due to its ability to inhibit the growth of cancer cells by blocking DNA synthesis and cell division. 

Synthesis

General procedure for the synthesis of methyl 2,3-diaminobenzoate from methyl 2-amino-3-nitrobenzoate: to a nitrogen-saturated solution of methyl 2-amino-3-nitrobenzoate (Chess GmbH, 50 g, 0.26 mol) in anhydrous ethanol (800 mL) was added palladium hydroxide (Degussa, 20% w/w carbon, 58.75% w/w water. 10g). The mixed slurry was degassed and stirred vigorously at room temperature under hydrogen (4 atm) atmosphere for 48 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under vacuum to give methyl 2,3-diaminobenzoate as a dark orange oil, which solidified to a solid after standing (43 g, 0.26 mol, 100% yield). Mass spectrometry analysis (m/z): calculated value of [M-OCH3]+ C8H10N2O2 was 135.05; measured value was 135.3.1H NMR (300 MHz, DMSO-d6) data: δ (ppm) 3.74 (s, 3H), 4.80 (br s, 1H), 6.20 (br s, 1H), 6.38 (t, 1H). 6.70 (d, 1H), 7.06 (d, 1H).

References

[1] Patent: US2006/270652, 2006, A1. Location in patent: Page/Page column 14
[2] Patent: WO2010/3048, 2010, A1. Location in patent: Page/Page column 117
[3] Patent: WO2008/157270, 2008, A1. Location in patent: Page/Page column 126
[4] Patent: EP1452528, 2004, A1. Location in patent: Page 22
[5] Patent: US2009/186879, 2009, A1. Location in patent: Page/Page column 50

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