2-aMino-5-cyanobenzoic acid

2-aMino-5-cyanobenzoic acid Property

Boiling point:

389.3±37.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.38±0.10(Predicted)

Appearance

Off-white to yellow Solid

Safety

RIDADR 

2811

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2916399090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

2-aMino-5-cyanobenzoic acid Chemical Properties,Usage,Production

Chemical Properties

Pale yellow solid

Synthesis

General procedure for the synthesis of 2-amino-5-cyanobenzoic acid from methyl 2-amino-5-cyanobenzoate: to a methanolic (200 mL) suspension of methyl 2-amino-5-cyanobenzoate (9.55 g, 54.2 mmol) was added an aqueous sodium hydroxide solution (30 mL, 6.0 M, 180 mmol). The reaction mixture was stirred at room temperature and a homogeneous solution was formed after 1 hour. After 27.5 hours of reaction, the solvent was removed by evaporation under reduced pressure and the residue was dissolved in water (300 mL). The resulting aqueous phase was washed with dichloromethane (2 x 200 mL) and subsequently acidified to acidity with concentrated hydrochloric acid (1 L). The product was extracted with ethyl acetate (500 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to give 8.57 g (97.5% yield) of yellow solid product, which could be used in subsequent reactions without further purification.

References

[1] Patent: WO2004/18428, 2004, A1. Location in patent: Page 347
[2] Patent: WO2014/93869, 2014, A1. Location in patent: Paragraph 0140
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8608 - 8621
[4] Patent: WO2004/18428, 2004, A1. Location in patent: Page 370
[5] Patent: WO2004/18414, 2004, A2. Location in patent: Page 136