Diphenylacetonitrile

Base Information

• Chemical Name: Diphenylacetonitrile
• CAS No.: 86-29-3
• Molecular Formula: C14H11N
• Molecular Weight: 193.248
• Hs Code.: 29269095
• European Community (EC) Number: 201-662-5
• NSC Number: 130268,884
• UNII: QK4W106TKU
• DSSTox Substance ID: DTXSID4020539
• Nikkaji Number: J4.937I
• Wikidata: Q27287309
• ChEMBL ID: CHEMBL3185477
• Mol file: 86-29-3.mol

Synonyms:DIPHENYLACETONITRILE;86-29-3;2,2-diphenylacetonitrile;Dipan;Diphenatrile;Benzhydrylcyanide;benzhydryl cyanide;Diphenylmethylcyanide;Benzyhydrylcyanide;Diphenylmethyl cyanide;Difenylacetonitril;Acetonitrile, diphenyl-;Diphenyl-alpha-cyanomethane;Benzeneacetonitrile, alpha-phenyl-;USAF KF-13;alpha-Phenylphenylacetonitrile;alpha-Phenylbenzeneacetonitrile;Caswell No. 396;alpha-Phenylbenzylcyanide;alpha-Cyanodiphenylmethane;Difenylacetonitril [Czech];Benzeneacetonitrile, .alpha.-phenyl-;Diphenyl-.alpha.-cyanomethane;Diphenyl acetonitrile;NSC 130268;.alpha.-Phenylphenylacetonitrile;EINECS 201-662-5;MFCD00001862;UNII-QK4W106TKU;.alpha.-Phenylbenzylcyanide;EPA Pesticide Chemical Code 037901;BRN 1911160;QK4W106TKU;AI3-17436;DTXSID4020539;NSC-884;NSC-130268;WLN: NCYR&R;DTXCID80539;CAS-86-29-3;diphenylacetonitril;diphenyl-acetonitrile;alpha-Phenylbenzyl cyanide;2,2-diphenyl-acetonitrile;Diphenylacetonitrile, 98%;.alpha.-Cyanodiphenylmethane;TimTec1_003810;Ph~2~C(H)CN;SCHEMBL181005;NSC884;CHEMBL3185477;.alpha.-Phenyl-benzeneacetonitrile;HMS1544N04;.ALPHA.-PHENYLBENZYL CYANIDE;Tox21_201556;Tox21_302854;NSC130268;STK700770;AKOS000120009;AM90235;CS-W015768;LS-7365;DIPHENYLACETIC ACID NITRILE [MI];NCGC00249068-01;NCGC00256362-01;NCGC00259105-01;AC-25261;AS-12052;BP-12820;DIPHENYLACETONITRILE [EP IMPURITY];SY008506;D0261;FT-0625250;FT-0667650;EN300-20197;D70408;a-Phenylbenzyl cyanide, a-Phenylphenylacetonitrile;A841600;AE-641/03255011;SR-01000393862;Q-201006;SR-01000393862-1;BRD-K12971880-001-01-6;Q27287309;METHADONE HYDROCHLORIDE IMPURITY E [EP IMPURITY];Z104477222;LEVOMETHADONE HYDROCHLORIDE IMPURITY E [EP IMPURITY]

Chemical Property of Diphenylacetonitrile

Chemical Property:

• Appearance/Colour: white to creamy or faint yellow crystalline powder
• Vapor Pressure: 0.000282mmHg at 25°C
• Melting Point: 71-73 °C(lit.)
• Refractive Index: 1.584
• Boiling Point: 322.3 °C at 760 mmHg
• Flash Point: 151.6 °C
• PSA: 23.79000
• Density: 1.076 g/cm³
• LogP: 3.34208
• Storage Temp.: Store below +30°C.
• Solubility.: INSOLUBLE
• Water Solubility.: INSOLUBLE
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 193.089149355
• Heavy Atom Count: 15
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

Diphenylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C1=CC=C(C=C1)C(C#N)C2=CC=CC=C2
• Uses: Mathadone (M225865) impurity. Used in synthesis of methadone, antispasmodics and other pharmaceuticals.Diphenylacetonitrile is used to synthesize isocyanate, which is further prepared into UV paint, PU paint, transparent elastomer and adhesive, etc. In addition, it is also used in polyamide and epoxy resin industries.

Technology Process of Diphenylacetonitrile

There total 143 articles about Diphenylacetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) + malononitrile (109-77-3) → Diphenylacetonitrile (86-29-3) + (2-cyanophenyl)acetonitrile (3759-28-2) + 2,2-diphenylmalononitrile (92427-55-9) + 2-(cyano(phenyl)methyl)benzonitrile (127667-03-2)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1039/b616768c

Reference yield:

C20H16FNO (198337-87-0) → benzophenone (119-61-9) + 2,2-diphenylacetamide (4695-13-0) + Diphenylacetonitrile (86-29-3) + N-(diphenylmethyl)acetamide (5267-35-6) + N-(diphenylmethylene)acetamide (22800-71-1) + 1-acetyl-3,3-diphenylaziridin-2-one (1375263-32-3) + 4-fluoroaniline (371-40-4)

Guidance literature:

With lithium perchlorate; In water; acetonitrile; Electrolysis;

DOI:10.1039/c2ob06878h

Reference yield:

diethyl ether (60-29-7,927820-24-4) + Bromodiphenylmethane (776-74-9) + cyanogen chloride (506-77-4) → Diphenylacetonitrile (86-29-3) + 1,1,2,2-tetraphenylethane (632-50-8) + diphenylchloromethane (90-99-3)

Guidance literature:

upstream raw materials:

ethanol

2,2-diphenyl-acetimidic acid ethyl ester; hydrochloride

2,2-diphenylacetamide

2,2,3,3-tetraphenylsuccinonitrile

Downstream raw materials:

3-morpholin-4-yl-2,2-diphenyl-propionitrile

2,2-diphenyl-4-pyrrolidino-butyronitrile

2,2-diphenyl-5-pyrrolidino-valeronitrile; hydrochloride

4-morpholin-4-yl-2,2-diphenyl-butyronitrile

Refernces

• 1、 Aesa,Baan,Novak,Szantay. "Preparation of unsaturated nitriles by the modification of Mitsunobu-Wilk procedure". . p. 1545 - 1550. Retrieved 1995.
• 2、 Hu, Dandan,Liu, Jiayue,Ren, Hongjun,Song, Jinyu,Zhang, Jun-Qi,Zhu, Guorong. "Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes". supporting information. p. 786 - 790. Retrieved 2022/01/28.
• 3、 Ansari, Tharique N.,Bihani, Manisha,Bora, Pranjal P.,Finck, Lucie,Handa, Sachin,Jasinski, Jacek B.,Leahy, David K.,Pavuluri, Bhavana. "Scalable α-Arylation of Nitriles in Aqueous Micelles using Ultrasmall Pd Nanoparticles: Surprising Formation of Carbanions in Water". . p. 6816 - 6821. Retrieved 2020/07/16.