2-Anilinobenzoic acid methyl ester

2-Anilinobenzoic acid methyl ester Property

Melting point:

58-59 °C

Boiling point:

140 °C(Press: 0.1 Torr)

Density 

1.175±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-1.27±0.20(Predicted)

Appearance

Off-white to gray Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Anilinobenzoic acid methyl ester Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of methyl 2-aminobenzoate from bromobenzene and methyl o-aminobenzoate: 15 g of methyl o-aminobenzoate, 15.6 g of bromobenzene, 0.9 g of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.4 g of tri-tert-butylphosphine (P(t-Bu)3), and 28.6 g of tertiary butylsodium alcohol (Na(t-BuO)) were added, under nitrogen protection, to a round bottom flask followed by addition of 100 mL of toluene as solvent. The mixture was stirred and heated to reflux. Upon completion of the reaction, the reaction mixture was cooled to room temperature and washed with dichloromethane and water. The organic layer was separated, dried over anhydrous magnesium sulfate (MgSO4), filtered and purified by column chromatography to give the final methyl 2-(phenylamino)benzoate in a yield of 21.0 g in 93%.

References

[1] Tetrahedron, 2006, vol. 62, # 48, p. 11100 - 11105
[2] Patent: TWI579270, 2017, B. Location in patent: Paragraph 0094; 0095
[3] Chemistry - A European Journal, 2006, vol. 12, # 13, p. 3636 - 3646
[4] Journal of Organic Chemistry, 2005, vol. 70, # 20, p. 8107 - 8109
[5] Patent: KR2016/102142, 2016, A. Location in patent: Paragraph 0215; 0218; 0219