1195-98-8

Basic information

• Product Name: 2-METHYL-2-PHENYLPROPANENITRILE
• Synonyms: 2-METHYL-2-PHENYLPROPANENITRILE;Dimethylphenylacetonitrile;A,A-DIMETHYLPHENYLACETONITRILE;benzeneacetonitrile, alpha,alpha-dimethyl-;2-methyl-2-phenylpropanenitrile(SALTDATA: FREE);2-Methyl-2-phenylpropionitrile, 2-Phenylisobutyronitrile;ZINC02144346;2-Phenylisobutyronitrile
• CAS NO: 1195-98-8
• Molecular Formula: C₁₀H₁₁N
• Molecular Weight: 145.2
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 1195-98-8.mol

Chemical Properties

• Boiling Point: 60 °C
• Flash Point: 101.4 °C
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.971 g/cm³
• Vapor Pressure: 0.0521mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-METHYL-2-PHENYLPROPANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-2-PHENYLPROPANENITRILE(1195-98-8)
• EPA Substance Registry System: 2-METHYL-2-PHENYLPROPANENITRILE(1195-98-8)

Safety Data

• Hazard Codes: Harmful:
• HazardClass: IRRITANT
• Hazardous Substances Data: 1195-98-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 1247, 1975 DOI: 10.1021/ja00838a051The Journal of Organic Chemistry, 34, p. 226, 1969 DOI: 10.1021/jo00838a051

InChI:InChI=1/C10H11N/c1-10(2,8-11)9-6-4-3-5-7-9/h3-7H,1-2H3

Upstream product

• 53310-47-7 α-Ethylthio-α-phenyl-propionitril 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 1823-91-2 1-phenylethyl cyanide 
• 542-69-8 1-iodo-butane 
• 103-79-7 1-phenyl-acetone 
• 100-47-0 benzonitrile 
• 75-03-6 ethyl iodide 
• 50654-53-0 2-lithio-2-methylpropionitrile 
• 1195-99-9 α,α-dimethylbenzyl isocyanide 
• 140-29-4 phenylacetonitrile 
• 78-82-0 Isobutyronitrile 
• 100-39-0 benzyl bromide 
• 74-83-9 methyl bromide 

Downstream Products

• 13740-70-0 2-methyl-1,2-diphenyl-propan-1-one 
• 119208-71-8 2-Methyl-1,2-diphenyl-1-propanimin 
• 100885-90-3 2-methyl-2-phenyl-1-[2]thienyl-propan-1-one 
• 826-55-1 2-methyl-2-phenylpropionic acid 
• 826-54-0 2-methyl-2-phenyl-propanamide 
• 17160-81-5 1-Cyclohexyl-2-methyl-2-phenyl-propan-1-one 
• 611-70-1 phenyl isopropyl ketone 
• 769-59-5 3-phenyl-butan-2-one 
• 71825-51-9 4-(2-cyanoprop-2-yl)-1-nitrobenzene 
• 3805-10-5 2,2-(dimethyl)-2-phenylacetaldehyde 
• 770-85-4 2-methyl-2-phenylbutan-3-one 
• 131556-45-1 (1S,2R)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-3-(1-methyl-1-phenyl-ethyl)-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl]-methanone 
• 131556-45-1 (1R,2S)-Bicyclo[2.2.1]hept-5-en-2-yl-[(S)-3-(1-methyl-1-phenyl-ethyl)-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl]-methanone 
• 131556-45-1 (1R,2R)-Bicyclo[2.2.1]hept-5-en-2-yl-[3-(1-methyl-1-phenyl-ethyl)-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl]-methanone 

Relevant articles and documents

Oxidative nucleophilic substitution of hydrogen in nitrobenzene with 2-phenylpropionitrile carbanion and potassium permanganate oxidant

The carbanion of 2-phenylpropionitrile adds to nitrobenzene in the p-position in liquid ammonia to give the relative stable σH-adduct which is oxidised with KMnO4 to 2-phenyl-2-(4-nitrophenyl)propionitrile; the relationships of rates of various reactions in these systems are estimated.

Nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O: Observation of unexpected regioselectivity

We describe the nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O to afford a variety of α-amino-α,β-unsaturated esters with high regioselectivities. The selective α-carboxylation of ynamides with this catalytic protocol is unexpected in view of the electronic bias of ynamides and is in sharp contrast to our previous study in which a stoichiometric amount of Ni(0) was used to form a β-carboxylated product exclusively. We revealed that this unexpected C-C bond formation was induced by the combination of Zn and MgBr2.

Reversible addition of carbon nucleophiles to some nitrogen-substituted η6-arenetricarbonylchromium(0) compounds

A study has been made of the nucleophilic addition/oxidation reactions of η6-1-methyl-1,2,3,4-tetrahydroquinolinetricarbonylchromium(0) (1), η6-1-methylindolinetricarbonylchromium(0) (2), and η6-2-N,N-dimethylaminotoluenetricarbonylchromium(0) (3) with the nucleophiles 2-lithio-2-methyl-propionitrile (A), 2-lithio-acetonitrile (B) and 2-lithio-2-methyl-1,3-dithiane (C).The regioselectivity in the addition of stabilized nucleophiles is time- and temperature-dependent, indicating the onset of thermodynamic control in prolonged/high temperature reactions.The addition is reversible, as indicated by crossover experiments with benzene-Cr(CO)3, the rate for dissociation of the C-C bond being strongly dependent on both the structure of the intermediate η5-cyclohexadienyltricarbonylchromium anions as well as the structure of the nucleophile.The regioselectivity of the addition/oxidation reaction can be optimized by an appropriate choice of reaction for each of the compounds 1, 2 and 3.

Synthesis of indolines by copper-mediated intramolecular aromatic C-H amination

A Cu(OAc)2-mediated intramolecular aromatic C-H amination proceeds with the aid of a picolinamide-type bidentate coordination group to deliver the corresponding indolines in good yields. The reaction occurs smoothly even under noble-metal-free conditions, and in some cases the use of an MnO2 terminal oxidant renders the process catalytic in Cu. The mild oxidation aptitude of Cu(OAc)2 and/or MnO2 accommodates the formation of electron-rich thiophene-and indole-fused indoline analogues. The Cu-based system can provide an effective approach to various indolines of potent interest in pharmaceutical and medicinal chemistry.

Palladium-Catalyzed Distal m-C-H Functionalization of Arylacetic Acid Derivatives

Herein, we present m-C-H olefination on derivatives of phenylacetic acids by tethering with a simple nitrile-based template through palladium catalysis. Notably, the versatility of the method is evaluated with a wide range of phenylacetic acid derivatives for obtaining the meta-olefination products in fair to excellent yields with outstanding selectivities under mild conditions. Significantly, the present strategy is successfully exemplified for the synthesis of drugs/natural product analogues (naproxen, ibuprofen, paracetamol, and cholesterol).

Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).

Cobalt-catalyzed C[sbnd]H activation/C[sbnd]O formation: Synthesis of benzofuranones

Herein, C[sbnd]H activation/C[sbnd]O formation reaction using novel cobalt catalytic system is reported. This reaction was given benzofuranones in moderate to excellent yields at room-temperature under air reaction conditions. The introduced strategy is efficient and low-cost method to synthesized benzofuranones from α,α-disubstitution acetic acid.

Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions

The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.

Synthesis of Tertiary Benzylic Nitriles via Nickel-Catalyzed Markovnikov Hydrocyanation of α-Substituted Styrenes

The Markovnikov hydrocyanation of α-substituted styrenes enables the synthesis of tertiary benzylic nitriles under nickel catalysis. The Lewis-acid-free transformation features an unprecedented functional groups tolerance, including the-OH and-NH2 groups. A broad range of tertiary benzylic nitriles were obtained in good to excellent yields. In addition, an asymmetric version of this reaction was preliminarily investigated.

Synthesis of Nitrile-Bearing Quaternary Centers by an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy

The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers by a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.