3-AMINO-5-NITROBENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

165-166°C (dec.)

Boiling point:

0°C

Density 

1.386±0.06 g/cm3(Predicted)

Flash point:

0°C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder

pka

1.34±0.10(Predicted)

color 

Yellow to red

InChI

InChI=1S/C8H8N2O4/c1-14-8(11)5-2-6(9)4-7(3-5)10(12)13/h2-4H,9H2,1H3

InChIKey

HZVBRLJDOZZHFL-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC([N+]([O-])=O)=CC(N)=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

Hazard Note 

Irritant

HS Code 

2922498590

3-AMINO-5-NITROBENZOIC ACID METHYL ESTER Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 3-amino-5-nitrobenzoate from methanol and 3-amino-5-nitrobenzoic acid: The esterification reaction was carried out by passing dry hydrogen chloride gas into a solution of methanol (160 ml) containing 5-amino-3-nitrobenzoic acid (18.5 g, 0.10 mol). After the solution was saturated, the reaction mixture was stirred at room temperature overnight. Subsequently, the mixture was concentrated to a crystalline residue. The residue was dissolved in dichloromethane and washed with 5% sodium bicarbonate solution until the pH of the aqueous phase reached 7-8. The organic phase was separated, dried over magnesium sulfate and evaporated to remove the solvent. The product 18.6 g was obtained in 94% yield.1H NMR (CDCl3) data: δ 8.21 (t, 1H, J=1.5Hz), 4.19 (br s, 2H), 3.96 (s, 3H).

References

[1] Organic Letters, 2013, vol. 15, # 17, p. 4442 - 4445
[2] Patent: WO2007/29587, 2007, A1. Location in patent: Page/Page column 35
[3] Patent: WO2007/55580, 2007, A1. Location in patent: Page/Page column 16
[4] Patent: EP1953163, 2008, A1. Location in patent: Page/Page column 12
[5] Patent: WO2004/50619, 2004, A1. Location in patent: Page 16

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