4-METHYLPHTHALIMIDE 99

4-METHYLPHTHALIMIDE 99 Property

Melting point:

196.5-199.5 °C(lit.)

Density 

1.301±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

10.09±0.20(Predicted)

form 

Solid

color 

Off-white to light brown

Safety

WGK Germany 

3

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

Precautionary statements

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

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

4-METHYLPHTHALIMIDE 99 Chemical Properties,Usage,Production

Uses

4-Methylphthalimide is a useful research chemical used in the preparation of imidobiaryls via ring opening reaction of cyclic diaryliodonium salts with imides by copper catalyst.

Synthesis

General procedure for the synthesis of 4-methylphthalimide from 5-methylisobenzofuran-1,3-dione (Intermediate Example 71): 5-methyl-2,3-dihydro-1H-isoindole xylene (15 mL) was added to a reaction vial containing 4-methylphthalic anhydride (3.0 g) and urea (1.2 g). The reaction mixture was stirred at 150°C overnight. After completion of the reaction, the mixture was cooled to room temperature and the precipitated crystals were collected by filtration and washed sequentially with ethanol and water. The resulting crystals were dried under reduced pressure to give 4-methylphthalimide (2.4 g, 82% yield) as white crystals.1H NMR (CDCl3) δ (ppm): 2.5 (3H, s), 7.5 (1H, d), 7.6 (1H, s), 7.7 (1H, s).

References

[1] Patent: EP1595866, 2005, A1. Location in patent: Page/Page column 27
[2] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 10, p. 1975 - 1976
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 14, p. 4159 - 4162
[4] Patent: EP1445249, 2004, A1. Location in patent: Page 133