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86-29-3

Basic Information
CAS No.: 86-29-3
Name: Benzeneacetonitrile, alpha-phenyl-
Article Data: 132
Cas Database
Molecular Structure:
Molecular Structure of 86-29-3 (Benzeneacetonitrile, alpha-phenyl-)
Formula: C14H11N
Molecular Weight: 193.248
Synonyms: Diphenyl acetonitriie;Diphenyl-alpha-cyanomethane;Diphenylmethyl-cyanide;Diphenyl acetonitrile;α-Phenylbenzylcyanide;α-phenyl-phenylacetonitrile;Diphenyl-α-cyanomethane;α-Cyanodiphenylmethane;alpha-Phenylbenzeneacetonitrile;Diphenyl-.alpha.-cyanomethane;Benzeneacetonitrile,R-phenyl-;Diphenatrile;alpha-Cyanodiphenylmethane;alpha-Phenylbenzylcyanide;Benzeneacetonitrile, .alpha.-phenyl-;Acetonitrile, diphenyl-;alpha-Phenylphenylacetonitrile;2,2-diphenylacetonitrile;
EINECS: 201-662-5
Density: 1.076 g/cm3
Melting Point: 71-73 °C(lit.)
Boiling Point: 322.3 °C at 760 mmHg
Flash Point: 151.6 °C
Solubility: Soluble in alcohol, ether
Appearance: white to creamy or faint yellow crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
Transport Information: N/A
PSA: 23.79000
LogP: 3.34208
Synthetic route
15795-74-1

1,1-diphenyl-2,2-dinitroethylene

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran for 2h; Ambient temperature;100%
7677-24-9

trimethylsilyl cyanide

5433-78-3

diphenylmethyl p-tolyl sulfone

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 25℃; for 1h; Inert atmosphere;100%
4695-13-0

2,2-diphenylacetamide

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;99%
With bis(trichloromethyl) carbonate; triethylamine In chloroform at 50℃; for 2h;87%
With palladium diacetate; Selectfluor; acetonitrile at 20℃; for 18h;84%
7677-24-9

trimethylsilyl cyanide

90-99-3

diphenylchloromethane

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With iodine; lithium carbonate In dichloromethane at 35℃; for 5h;99%
With titanium tetrachloride In dichloromethane at 0℃; for 2h;93%
41401-03-0

diphenyl-acetaldehyde-oxime

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In dichloromethane; 1,2-dichloro-ethane for 0.0833333h; Ambient temperature;98%
With 4-nitro-1-((trifluoromethyl)sulfonyl)-1H-imidazole; triethylamine In acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Sealed tube;78%
2997-21-9

2,2-diphenyl-pentanedinitrile

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
IrH5(P-(i-Pr)3)2 In toluene at 150℃; for 12h;98%
91-01-0

1,1-Diphenylmethanol

7677-24-9

trimethylsilyl cyanide

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With iodine; lithium carbonate In dichloromethane at 35℃; for 5h;98%
With tris(pentafluorophenyl)borate In acetonitrile at 20℃; for 1h;93%
With zinc trifluoromethanesulfonate In nitromethane at 100℃; for 5.5h;90%
With 3-dodecyl-2-iodo-1-methyl-1H-imidazol-3-ium hexafluoroantimonate; iodine In nitromethane at 20℃; for 2h; Inert atmosphere;46%
7677-24-9

trimethylsilyl cyanide

1016-09-7

benzhydryl methyl ether

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With gold(III) chloride In dichloromethane at 20℃; for 0.0833333h; Reagent/catalyst; Time; Inert atmosphere;96%
108-86-1

bromobenzene

140-29-4

phenylacetonitrile

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With P(i-BuNCH2CH2)3N; sodium hexamethyldisilazane; palladium diacetate In toluene at 100℃; for 6h;93%
With potassium phosphate; dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane; palladium diacetate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; Sealed tube;89%
With potassium hydroxide In water at 45℃; for 17h;84%
With caesium carbonate; triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 130℃; for 2h; Phenylation;44%
606-83-7

3,3-Diphenylpropionic acid

86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With trifluoroacetic acid; trifluoroacetic anhydride; sodium nitrite at 20℃; nitrosative cleavage;93%
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Consensus Reports

Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

Specification

The Diphenylacetonitrile with CAS registry number of 86-29-3 is also known as Diphenyl-alpha-cyanomethane. The IUPAC name is 2,2-Diphenylacetonitrile. It belongs to product categories of Pharmaceutical Intermediates; Aromatic Nitriles; C10 to C27; Cyanides/Nitriles; Nitrogen Compounds. Its EINECS registry number is 201-662-5. In addition, the formula is C14H11N and the molecular weight is 193.24. This chemical is a white crystal.

Physical properties about Diphenylacetonitrile are: (1)ACD/LogP: 3.30; (2)ACD/LogD (pH 5.5): 3.3; (3)ACD/LogD (pH 7.4): 3.3; (4)ACD/BCF (pH 5.5): 189.12; (5)ACD/BCF (pH 7.4): 189.12; (6)ACD/KOC (pH 5.5): 1483.54; (7)ACD/KOC (pH 7.4): 1483.54; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.584; (11)Molar Refractivity: 60.11 cm3; (12)Molar Volume: 179.4 cm3; (13)Surface Tension: 45 dyne/cm; (14)Density: 1.076 g/cm3; (15)Flash Point: 151.6 °C; (16)Enthalpy of Vaporization: 56.41 kJ/mol; (17)Boiling Point: 322.3 °C at 760 mmHg; (18)Vapour Pressure: 0.000282 mmHg at 25 °C.

Preparation of Diphenylacetonitrile: it is prepared by reaction of 2,2-diphenyl-acetamide. The reaction needs reagents bis(trichloromethyl) carbonate, triethylamine and solvent CHCl3 at the temperature of 50 °C for 2 hours. The yield is about 87%.

Diphenylacetonitrile is prepared by reaction of 2,2-diphenyl-acetamide.

Uses of Diphenylacetonitrile: it is used to produce benzophenone. The reaction occurs with reagents O2, K2CO3 and solvents dimethylsulfoxide, H2O at ambient temperature. The yield is about 95%.

Diphenylacetonitrile is used to produce benzophenone.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C=C1)C(C#N)C2=CC=CC=C2
2. InChI: InChI=1S/C14H11N/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H
3. InChIKey: NEBPTMCRLHKPOB-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 3500mg/kg (3500mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 155, 1971.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04134,
rat LD50 oral 3500mg/kg (3500mg/kg)   Residue Reviews. Vol. 10, Pg. 97, 1965.

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