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Diphenylacetic acid

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Diphenylacetic acid
Names
Other names
2,2-diphenylacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.805 Edit this at Wikidata
EC Number
  • 204-185-0
UNII
  • InChI=1S/C14H12O2/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,(H,15,16)
    Key: PYHXGXCGESYPCW-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)C(=O)O
Properties
C14H12O2
Molar mass 212.24 g/mol
Density g/cm3
Melting point 147–149 °C (297–300 °F; 420–422 K)
Hazards
GHS labelling:[1]
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H302, H311, H315, H319, H331, H332, H335, H400
P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diphenylacetic acid is an organic chemical with applications in drug synthesis.[1][2][3]

Applications

[edit]
  1. AB06-117 (cmp #23)[4]
  2. Adiphenine
  3. Arpenal
  4. Asimadoline
  5. 2,2-DEP [36794-51-1]
  6. Desmethylmoramide
  7. Diphenamide [de] [957-51-7] Herbicide
  8. Dioxaphetyl butyrate
  9. Fluperamide
  10. Loperamide
  11. PD-85639
  12. Moramide
  13. Pifenate[5]
  14. Tropacine
  15. BIBO-3304 [191868-13-0]
  16. BIBP-3226
  17. PC4225440[6]

Synthesis

[edit]
  • Alternative procedure:[9]
  • From glyoxylic acid and benzene:[13]

See also

[edit]

References

[edit]
  1. ^ Jena, A. (January 1870). "Ueber die Benzilsäure oder Diphenylglycolsäure". Justus Liebigs Annalen der Chemie. 155 (1): 77–89. doi:10.1002/jlac.18701550107.
  2. ^ Symons, R., Zincke, Th. (July 1873). "Ueber Diphenylessigsäure und Benzilsäure". Berichte der Deutschen Chemischen Gesellschaft. 6 (2): 1188–1191. doi:10.1002/cber.187300602102.
  3. ^ Symons, R., Zincke, Th. (January 1874). "Ueber Benzilsäure und Diphenylessigsäure". Justus Liebigs Annalen der Chemie. 171 (1): 117–134. doi:10.1002/jlac.18741710110.
  4. ^ Bonifazi, Alessandro; Battiti, Francisco O.; Sanchez, Julie; Zaidi, Saheem A.; Bow, Eric; Makarova, Mariia; Cao, Jianjing; Shaik, Anver Basha; Sulima, Agnieszka; Rice, Kenner C.; Katritch, Vsevolod; Canals, Meritxell; Lane, J. Robert; Newman, Amy Hauck (2021). "Novel Dual-Target μ-Opioid Receptor and Dopamine D3 Receptor Ligands as Potential Nonaddictive Pharmacotherapeutics for Pain Management". Journal of Medicinal Chemistry. 64 (11): 7778–7808. doi:10.1021/acs.jmedchem.1c00611. PMC 9308496. PMID 34011153.
  5. ^ GB granted 939019, Temple, Richard William; Wiggins, Leslie Frederick, assigned to Aspro Nicholas Ltd 
  6. ^ Urbani, P., Cascio, M. G., Ramunno, A., Bisogno, T., Saturnino, C., Marzo, V. D. (August 2008). "Novel sterically hindered cannabinoid CB1 receptor ligands". Bioorganic & Medicinal Chemistry. 16 (15): 7510–7515. doi:10.1016/j.bmc.2008.06.001.
  7. ^ Demselben (January 1893). "Beiträge zur Kenntniss der Diphenylessigsäure". Justus Liebigs Annalen der Chemie. 275 (1): 83–89. doi:10.1002/jlac.18932750107.
  8. ^ "Diphenylacetic Acid". Organic Syntheses. 3: 45. 1923. doi:10.15227/orgsyn.003.0045.
  9. ^ Strazzolini, P., Giumanini, A. G., Verardo, G. (December 1987). "Diphenylacetic Acid from Benzilic Acid: An Ecologically and Economically Improved Procedure". Synthetic Communications. 17 (16): 1919–1928. doi:10.1080/00397918708057804.
  10. ^ Fritsch, P., Feldmann, F. (January 1899). "Synthese aromatisch disubstituirter Essigsäuren mittelst Chloral". Justus Liebigs Annalen der Chemie. 306 (1–2): 72–86. doi:10.1002/jlac.18993060106.
  11. ^ Kesslin, George, U.S. patent 2,756,254 (1952 to Kay-Fries Chemicals Inc).
  12. ^ Herbert R Elkinton, Kesslin George, & Nicholl Leonard, U.S. patent 2,517,856 (1950 to Kay-Fries Chemicals Inc).
  13. ^ Prakash, G. K. S., Paknia, F., Kulkarni, A., Narayanan, A., Wang, F., Rasul, G., Mathew, T., Olah, G. A. (March 2015). "Taming of superacids: PVP-triflic acid as an effective solid triflic acid equivalent for Friedel–Crafts hydroxyalkylation and acylation". Journal of Fluorine Chemistry. 171: 102–112. Bibcode:2015JFluC.171..102P. doi:10.1016/j.jfluchem.2014.08.020.
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