Chemistry:Homophthalic acid

From HandWiki
Homophthalic acid
Names
Preferred IUPAC name
2-(Carboxymethyl)benzoic acid
Other names
α-Carboxy-o-toluic acid
Carboxyphenyl acetic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 66643
UNII
Properties
C9H8O4
Molar mass 180.159 g·mol−1
Appearance Off-white to light yellow or pale green
Melting point 181 °C (358 °F; 454 K)[2]
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Homophthalic acid is a dicarboxylic acid with the formula C6H4(CO2H)CH2CO2H. It is a colorless solid. The compounds can be prepared by the Willgerodt reaction from 2-acetylbenzoic acid.[3]

One of the uses is in the preparation of the NSAID tesicam.

Further reading

  • Use of homophthalic anhydride: Manoni, Francesco; Connon, Stephen J. (2014). "Catalytic Asymmetric Tamura Cycloadditions". Angewandte Chemie International Edition 53 (10): 2628–2632. doi:10.1002/anie.201309297. PMID 24573916. 

References

  1. "Compound Record". http://ops.rsc.org/Compounds/Get/670357. 
  2. "Homophthalic Acid". https://www.chemspider.com/Chemical-Structure.60010.html. 
  3. Schwenk, Erwin; Papa, Domenick (1946). "Preparation of Aryl Aliphatic Acids by the Modified Willgerodt Reaction". The Journal of Organic Chemistry 11 (6): 798–802. doi:10.1021/jo01176a023. PMID 20282506.