Diphenylacetonitrile

Diphenylacetonitrile
Names
	Other names 2,2-Diphenylacetonitrile, Dipan, Diphenatrile, Benzhydrylcyanide.
Identifiers
CAS Number	86-29-3;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3185477;
ChemSpider	6576;
ECHA InfoCard	100.001.511
EC Number	201-662-5;
PubChem CID	6837;
UNII	QK4W106TKU;
CompTox Dashboard (EPA)	DTXSID4020539 ;
	InChI InChI=1S/C14H11N/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H Key: NEBPTMCRLHKPOB-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)C(C#N)C2=CC=CC=C2;
Properties
Chemical formula	C14H11N
Molar mass	193.24 g/mol
Density	1.1061g/cm3 (estimated)
Melting point	71–73 °C (160–163 °F; 344–346 K)
Boiling point	181 °C (358 °F; 454 K) ; @ 12 mmHg
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, 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

Diphenylacetonitrile is an organic chemical with a wide variety of uses in the pharmaceutical industry.

Synthesis

In Hoch’s original procedure, phenylacetonitrile is brominated to give bromobenzyl cyanide, and reaction of this with benzene in the presence of aluminium trichloride gives diphenylacetonitrile.^[2]^[3]^[4]^[5]^[6]

Applications

Opioid analgesics: Bezitramide, Dipipanone, Dipyanone, Isomethadol, LAAM, Methadone, Noracymethadol, Normethadone, Norpipanone, Piritramide, R-4066, R 4837 [59708-47-3], R 5260 [1109-69-9] (25ii):^[7]
Antispasmodics: Aminopentamide,^[8] Buzepide,^[9] Fenpiverinium, Fenpipramide
Psychostimulants: 2-Benzhydrylpiperazine [28217-87-0],^[10]^[11] Desoxypipradrol
- Urinary incontinence: Darifenacin, Imidafenacin
Anti-diarrhoeals: Difenoxin, Diphenoxylate, Nufenoxole
Choleretic and spasmolytic agent: Diisopromine
Analeptic (respiratory stimulant): Doxapram
Antiarrhythmic: Isopropanamide^[12]^[13]
Antidepressant: McN-4187^[14]
Cytochromes P450 inhibitor: Proadifen

References

^ "Diphenylacetonitrile". PubChem. U.S. National Library of Medicine.
^ Hoch J (1933). "General method for the preparation of di- and triarylacetonitriles". Compt. Rend. 197: 770–772.
^ Reid WB, Hunter JH (October 1948). "Preparation of diphenylacetonitrile". Journal of the American Chemical Society. 70 (10): 3515. Bibcode:1948JAChS..70.3515R. doi:10.1021/ja01190a509. PMID 18891916.
^ Robb CM, Schultz EM (1948). Arnold RT, Britain JW (eds.). "Diphenylacetonitrile". Organic Syntheses. 28: 55. doi:10.15227/orgsyn.028.0055.
^ Ginsburg D, Baizer MM (June 1949). "Diphenylacetonitrile". Journal of the American Chemical Society. 71 (6): 2254. Bibcode:1949JAChS..71Q2254G. doi:10.1021/ja01174a512.
^ Kasarekar RB, Sawant SB (January 1987). "Preparation of diphenyl acetonitrile by phase transfer catalysis". Journal of Chemical Technology & Biotechnology. 38 (3): 201–208. Bibcode:1987JCTB...38..201K. doi:10.1002/jctb.280380306.
^ Leysen, J., Tollenaere, J. P., Koch, M. H. J., Laduron, P. (June 1977). "Differentiation of opiate and neuroleptic receptor binding in rat brain". European Journal of Pharmacology. 43 (3): 253–267. doi:10.1016/0014-2999(77)90025-5. PMID 194781.
^ Ginsburg D, Baizer MM (August 1957). "Antispasmodics. X. α,α-Diphenyl-γ-amino Amides 1". Journal of the American Chemical Society. 79 (16): 4451–4457. Bibcode:1957JAChS..79.4451M. doi:10.1021/ja01573a056.
^ Janssen PA, Demoen PJ, Jageneau AH, Loomans JL (April 1959). "The influence of heterocyclic ring size of tertiary 2, 2-diphenyl-4-amino-butyramides on parasympatholytic activity". Journal of Medicinal and Pharmaceutical Chemistry. 1 (2): 187–194. doi:10.1021/jm50003a007. PMID 13665290.
^ Jongh David Karel De, Akkerman Antonie Marie, Kofman Hendrik,& Vries George De, US2997473 (1961 to Nederlandsche Combinatie voor Chemische Industrie NV).
^ Karel De Jongh David, et al. GB893391 (1962 to Nederlandsche Combinatie voor Chemische Industrie NV).
^ JANSSEN P, ZIVKOVIC D, DEMOEN P, DE JONGH DK, VAN PROOSDIJ-HARTZEMA EG. Substituted phenylpropylamines. I. Synthesis and physicochemical properties of basic butyronitriles and butyramides. Arch Int Pharmacodyn Ther. 1955 Sep 1;103(1):82-99. PMID: 13259723.
^ Janssen Paul Adriaan Jan & Jongh David Karel De, US2884436 (1959 to Nederlandsche Combinatie voor Chemische Industrie NV).
^ Maryanoff BE, Nortey SO, Gardocki JF (August 1984). "Structure-activity studies on antidepressant 2,2-diarylethylamines". Journal of Medicinal Chemistry. 27 (8): 1067–1071. doi:10.1021/jm00374a022. PMID 6747990.

[1] "Diphenylacetonitrile". PubChem. U.S. National Library of Medicine.

[2] Hoch J (1933). "General method for the preparation of di- and triarylacetonitriles". Compt. Rend. 197: 770–772.

[3] Reid WB, Hunter JH (October 1948). "Preparation of diphenylacetonitrile". Journal of the American Chemical Society. 70 (10): 3515. Bibcode:1948JAChS..70.3515R. doi:10.1021/ja01190a509. PMID 18891916.

[4] Robb CM, Schultz EM (1948). Arnold RT, Britain JW (eds.). "Diphenylacetonitrile". Organic Syntheses. 28: 55. doi:10.15227/orgsyn.028.0055.

[5] Ginsburg D, Baizer MM (June 1949). "Diphenylacetonitrile". Journal of the American Chemical Society. 71 (6): 2254. Bibcode:1949JAChS..71Q2254G. doi:10.1021/ja01174a512.

[6] Kasarekar RB, Sawant SB (January 1987). "Preparation of diphenyl acetonitrile by phase transfer catalysis". Journal of Chemical Technology & Biotechnology. 38 (3): 201–208. Bibcode:1987JCTB...38..201K. doi:10.1002/jctb.280380306.

[7] Leysen, J., Tollenaere, J. P., Koch, M. H. J., Laduron, P. (June 1977). "Differentiation of opiate and neuroleptic receptor binding in rat brain". European Journal of Pharmacology. 43 (3): 253–267. doi:10.1016/0014-2999(77)90025-5. PMID 194781.

[8] Ginsburg D, Baizer MM (August 1957). "Antispasmodics. X. α,α-Diphenyl-γ-amino Amides 1". Journal of the American Chemical Society. 79 (16): 4451–4457. Bibcode:1957JAChS..79.4451M. doi:10.1021/ja01573a056.

[9] Janssen PA, Demoen PJ, Jageneau AH, Loomans JL (April 1959). "The influence of heterocyclic ring size of tertiary 2, 2-diphenyl-4-amino-butyramides on parasympatholytic activity". Journal of Medicinal and Pharmaceutical Chemistry. 1 (2): 187–194. doi:10.1021/jm50003a007. PMID 13665290.

[10] Jongh David Karel De, Akkerman Antonie Marie, Kofman Hendrik,& Vries George De, US2997473 (1961 to Nederlandsche Combinatie voor Chemische Industrie NV).

[11] Karel De Jongh David, et al. GB893391 (1962 to Nederlandsche Combinatie voor Chemische Industrie NV).

[12] JANSSEN P, ZIVKOVIC D, DEMOEN P, DE JONGH DK, VAN PROOSDIJ-HARTZEMA EG. Substituted phenylpropylamines. I. Synthesis and physicochemical properties of basic butyronitriles and butyramides. Arch Int Pharmacodyn Ther. 1955 Sep 1;103(1):82-99. PMID: 13259723.

[13] Janssen Paul Adriaan Jan & Jongh David Karel De, US2884436 (1959 to Nederlandsche Combinatie voor Chemische Industrie NV).

[14] Maryanoff BE, Nortey SO, Gardocki JF (August 1984). "Structure-activity studies on antidepressant 2,2-diarylethylamines". Journal of Medicinal Chemistry. 27 (8): 1067–1071. doi:10.1021/jm00374a022. PMID 6747990.

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