4-Methylphthalic anhydride Chemical Properties

Melting point:

90-92 °C(lit.)

Boiling point:

295 °C(lit.)

Density 

1.2599 (rough estimate)

refractive index 

1.5380 (estimate)

storage temp. 

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

form 

Flakes or Crystalline Powder

color 

White to yellow-orange

Water Solubility 

insoluble

InChI

InChI=1S/C9H6O3/c1-5-2-3-6-7(4-5)9(11)12-8(6)10/h2-4H,1H3

InChIKey

ZOXBWJMCXHTKNU-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=C(C)C=C2)C(=O)O1

CAS DataBase Reference

19438-61-0(CAS DataBase Reference)

NIST Chemistry Reference

4-Methylphthalic anhydride(19438-61-0)

EPA Substance Registry System

1,3-Isobenzofurandione, 5-methyl- (19438-61-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36-36/37/39

WGK Germany 

3

HS Code 

29173990

MSDS

• Language:English Provider:Resorcinol dibenzoate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

4-Methylphthalic anhydride Usage And Synthesis

Uses

4-Methylphthalic anhydride (4-MPA) is mainly used as an important intermediate in the synthesis of herbicides, especially several cereal herbicides, and can also be used as an intermediate in the synthesis of dyes.

Chemical Properties

white to yellow-orange flakes or

Synthesis

The general procedure for the synthesis of 5-methylisobenzofuran-1,3-dione from 4-methylphthalic acid was as follows: 10.0 g of 4-methylphthalic acid and a solvent mixture consisting of 20 mL of N,N-dimethylacetamide, 100 mL of chlorobenzene, and 40 mL of toluene were added to a 300 mL three-necked flask at room temperature and under nitrogen protection. The reaction mixture was heated to 111 °C and the reaction was stirred at this temperature for 10 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the resulting crude product was washed with toluene and dispersed to give 3.6 g of 4-methylphthalic anhydride.

References

[1] Organic Letters, 2010, vol. 12, # 21, p. 4796 - 4799
[2] Monatshefte fuer Chemie, 1891, vol. 12, p. 626
[3] Patent: US2016/376285, 2016, A1. Location in patent: Paragraph 0121

4-Methylphthalic anhydride(19438-61-0)Related Product Information

• Methylhexahydrophthalic anhydride
• Trifluoromethanesulfonic anhydride
• Succinic anhydride
• 3,3',4,4'-Biphenyltetracarboxylic dianhydride
• Methyl tetrahydrophthalic anhydride
• CIS-BUTENEDIOIC ANHYDRIDE
• cis-1,2,3,6-Tetrahydrophthalic anhydride
• Isatoic Anhydride
• Glutaric anhydride
• Phthalic anhydride
• Resorcinol
• 3,4-Dimethylaniline
• 2,4-Dimethyl aniline
• 4-METHACRYLOXYETHYL TRIMELLITIC ANHYDRIDE
• Trimellitic Anhydride
• 4-tert-Butylphthalic anhydride
• TETRAPHENYLPHTHALIC ANHYDRIDE
• Acetic anhydride