Methyl 2-amino-3-chlorobenzoate Chemical Properties

Melting point:

35-37°C

Boiling point:

273.8±20.0 °C(Predicted)

Density 

1.311±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to lump

pka

0.25±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C8H8ClNO2/c1-12-8(11)5-3-2-4-6(9)7(5)10/h2-4H,10H2,1H3

InChIKey

MSXSZFYRADEEJA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

77820-58-7(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 2-amino-3-chloro-, methyl ester (77820-58-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

HS Code 

2922390090

Methyl 2-amino-3-chlorobenzoate Usage And Synthesis

Application

Methyl 2-amino-3-chlorobenzoate is an important pharmaceutical and chemical intermediate. It is a key intermediate in the synthesis of the triazolidinesulfonamide herbicide chlorpyrifos and is used in the synthesis of many pesticides.

Chemical Properties

off-white crystalline powder

Synthesis

The general procedure for the synthesis of methyl 2-amino-3-chlorobenzoate from methyl 2-nitro-3-chlorobenzoate was as follows: iron powder (1.94 g, 34.8 mmol) was added to an ethanol/acetic acid (100 mL/100 mL) solution of methyl 3-chloro-2-nitrobenzoate (2.5 g, 11.6 mmol) at room temperature. Subsequently, the suspension was refluxed for 2 h under nitrogen protection. After completion of the reaction, it was cooled to room temperature and the solvent was partially removed by rotary evaporator. The resulting residue was partitioned between water/ethyl acetate (200 mL/300 mL). The organic phase was separated and washed sequentially with 1N aqueous sodium hydroxide (50 mL), brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated by rotary evaporator to afford the target product, methyl 2-amino-3-chlorobenzoate, as a tan oily substance (1.7 g, 79% yield), which was converted to a waxy solid upon standing. The crude product was pure enough to be used in subsequent steps without further purification. The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.86 (s, 3H), 6.25 (s, 2H), 6.57 (t, J = 7.93 Hz, 1H), 7.39 (dd, J = 7.81, 1.51 Hz, 1H), 7.79 (dd, J = 8.06, 1.51 Hz, 1H). Mass spectrometry analysis showed a molecular ion peak of 185.95 (MH+) and a calculated value of 185.02 for C8H8ClNO2.

Toxics Screening Level

The ITSL for Methyl 2-amino-3-chlorobenzoate is 7 μg/m3 based on an annual averaging time.

References

[1] Patent: US2006/94707, 2006, A1. Location in patent: Page/Page column 64
[2] Patent: US2007/259850, 2007, A1. Location in patent: Page/Page column 99
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754

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