Diphenylacetic acid

Diphenylacetic acid

Names
Other names 2,2-diphenylacetic acid
Identifiers
CAS Number	117-34-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:41967
ChEMBL	ChEMBL1232181
ChemSpider	8030
DrugBank	DB03588
ECHA InfoCard	100.003.805
EC Number	204-185-0
PubChem CID	8333
UNII	658NCZ0NKO
CompTox Dashboard (EPA)	DTXSID0059453
InChI 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
SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)C(=O)O
Properties
Chemical formula	C14H12O2
Molar mass	212.24 g/mol
Density	g/cm3
Melting point	147–149 °C (297–300 °F; 420–422 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311, H315, H319, H331, H332, H335, H400
Precautionary statements	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). Infobox references

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

Applications

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

• From hydroiodic acid reduction of benzoin. ^{[7] [8]}

• Alternative procedure: ^[9]

• From chloral and benzene: ^{[10] [11] [12]}

• From glyoxylic acid and benzene: ^[13]

See also

• Diphenylacetonitrile

References

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. GBgranted 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.