Methyl 3,4-diaminobenzoate Chemical Properties

Melting point:

105-110 °C

Boiling point:

376.9±22.0 °C(Predicted)

Density 

1.260±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.02±0.10(Predicted)

color 

White to Gray to Red

BRN 

2091675

InChI

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

InChIKey

IOPLHGOSNCJOOO-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

36692-49-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22-22

Safety Statements 

26-36/37/39-36/37

RIDADR 

2811

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29224999

MSDS

• Language:English Provider:Methyl 3,4-diaminobenzoate
• Language:English Provider:ALFA

Methyl 3,4-diaminobenzoate Usage And Synthesis

Application

Methyl 3,4-diaminobenzoate can be used as a drug molecule and organic synthesis intermediate in laboratory research and development.

Chemical Properties

White to light brown to light yellow powder or crystals

Synthesis

Thionyl chloride (0.72 mL, 9.80 mmol) was slowly added dropwise to a solution of 3,4-diaminobenzoic acid (1.00 g, 6.58 mmol) in methanol (15.0 mL) for a controlled time of 10 minutes. The reaction mixture was stirred at room temperature for 4 hours before the solvent was removed by evaporation under reduced pressure. The residue was partitioned between water and ethyl acetate (EtOAc) to separate the organic layer. The organic layer was diluted with ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate, saturated brine and water and then dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to afford methyl 3,4-diaminobenzoate (993 mg, 95.0% yield) as a brown solid. The product characterization data were as follows: 1H NMR (CDCl3, 500 MHz) δ 7.49 (d, 1H, J = 7.01 Hz, Ar-H), 7.47 (s, 1H, Ar-H), 6.68 (d, 1H, J = 7.01 Hz, Ar-H), 3.87 (s, 3H, -COOCH3), 3.80 (br s, 2H, -NH2 ), 3.35 (br s, 2H, -NH2); 13C NMR (CDCl3, 125 MHz) δ 166.56, 140.89, 138.16, 120.87, 118.23, 118.16, 52.11; LCMS m/z calculated value (MNa)+ 189.06, measured value 189.00.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7456 - 7460
[2] Patent: US2016/33489, 2016, A1. Location in patent: Paragraph 0204
[3] Medicinal Chemistry Research, 2015, vol. 24, # 8, p. 3143 - 3156
[4] Patent: WO2005/113489, 2005, A1. Location in patent: Page/Page column 75-76
[5] Patent: EP1502916, 2005, A1. Location in patent: Page 440

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