5558-29-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Isopropyl-2-phenylacetonitrile is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its ability to form disubstituted aminopiperidines makes it a valuable reagent in the synthesis of calcium channel blockers, which are essential for treating pain and neuropathic pain.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Isopropyl-2-phenylacetonitrile serves as a reagent for the production of various organic compounds. It is particularly useful in the synthesis of (methylethyl)(oxopropyl)benzeneacetonitrile and noremopamil enantiomers, which have potential applications in the development of new drugs and materials.

InChI:InChI=1/C11H13N/c1-9(2)11(8-12)10-6-4-3-5-7-10/h3-7,9,11H,1-2H3/t11-/m1/s1

Upstream product

• 140-29-4 phenylacetonitrile 
• 75-26-3 isopropyl bromide 
• 21101-81-5 ethyl 2-cyano-3-methyl-2-phenylbutanoate 
• 591-50-4 iodobenzene 
• 21658-95-7 diisopropyl (cyanomethyl)phosphonate 
• 936-26-5 rac-1-chloro-2-methyl-1-phenylpropane 
• 75-30-9 2-iodo-propane 
• 75-29-6 isopropyl chloride 
• 60586-49-4 2-amino-3,3-dimethylpropionitrile hydrochloride 
• 98-80-6 phenylboronic acid 
• 538-93-2 1-phenyl-2-methylpropane 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 67-63-0 isopropyl alcohol 
• 611-70-1 phenyl isopropyl ketone 

Downstream Products

• 5470-47-3 (±)-3-methyl-2-phenylbutyramide 
• 3508-94-9 3-methyl-2-phenylbutyric acid 
• 109560-36-3 2-isopropyl-3-methyl-2-phenyl-4-piperidino-butyronitrile 
• 101876-90-8 2,2-diphenyl-3-methylbutanenitrile 
• 1224-39-1 3-methyl-2-(2-morpholin-4-yl-ethyl)-2-phenyl-butyronitrile 
• 29850-96-2 2-Isopropyl-2-phenylhexannitril 
• 15934-57-3 3-phenyl-4-methylpentan-2-one 
• 69309-44-0 2-Butylsulfanyl-3-methyl-2-phenyl-butyronitrile 
• 22180-13-8 4-Methyl-3-phenyl-3-cyan-valeriansaeure-t-butylester 
• 33672-10-5 2-(2-Chloro-4-nitro-phenyl)-3-methyl-2-phenyl-butyronitrile 
• 33092-37-4 2-(2-Benzoyl-4-nitro-phenyl)-3-methyl-2-phenyl-butyronitrile 
• 55233-21-1 2-(4-Amino-phenyl)-3-methyl-2-phenyl-butyronitrile 
• 55233-06-2 3-Methyl-2-(4-nitro-phenyl)-2-phenyl-butyronitrile 
• 58422-72-3 α-Peracetoxy-α-phenylisovaleronitril 

Relevant academic research and scientific papers

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

Cobalt-Catalyzed Alkylation of Nitriles with Alcohols

Herein, we report an operationally convenient, cobalt-catalyzed alkylation of aryl nitriles employing primary and secondary alcohols (>30 examples, up to 86% yield). The use of readily available cobalt precursors and the widely employed BIAN (BIAN = bis(a

Asymmetric Deoxygenative Cyanation of Benzyl Alcohols Enabled by Synergistic Photoredox and Copper Catalysis?

Summary of main observation and conclusion. An enantioselective deoxygenative cyanation of benzyl alcohols was accomplished for the first time through the synergistic photoredox and copper catalysis. This reaction features the use of organic photosensitizer and low-cost 3d metal catalyst, simple and safe operations, and extremely mild conditions. A variety of chiral benzyl nitriles were produced in generally good yields and high level of enantiocontrols from readily available feedstocks (22 examples, up to 93% yield and 92% ee).

Enantioseparation of Sulfoxides and Nitriles by Inclusion Crystallization with Chiral Organic Salts Based on l-Phenylalanine

Enantioselective inclusion of aromatic sulfoxides and nitriles was achieved in a host framework created by organic salts comprising achiral benzoic acids and a chiral primary amine (1a) derived from l-phenylalanine. Tuning of the combined achiral acid component successfully changed the chiral recognition ability of the organic salts. The guest molecules were hydrogen-bonded to form three-component inclusion crystals, and the enantiomers of nitriles and sulfoxides were separated with high selectivity up to 92 and 98 % ee. As far as we know, this is the first example of the enantioseparation of non-functionalized aromatic nitriles.

Enantioselective Rhodium-Catalyzed Allylic Alkylation of Prochiral α,α-Disubstituted Aldehyde Enolates for the Construction of Acyclic Quaternary Stereogenic Centers

A highly enantioselective rhodium-catalyzed allylic alkylation of prochiral α,α-disubstituted aldehyde enolates with allyl benzoate is described. This protocol provides a novel approach for the synthesis of acyclic quaternary carbon stereogenic centers and it represents the first example of the direct enantioselective alkylation of an aldehyde enolate per se. The versatility of the α-quaternary aldehyde products is demonstrated through their conversion to a variety of useful motifs applicable to target-directed synthesis. Finally, mechanistic studies indicate that high levels of asymmetric induction are achieved from a mixture of prochiral (E)- and (Z)-enolates, which provides an exciting development for this type of transformation.

Enantioselective rhodium-catalyzed allylic substitution with a nitrile anion:construction of acyclic quaternary carbon stereogenic centers

A direct and highly enantioselective rhodium-catalyzed allylic alkylation of allyl benzoate with α-substituted benzyl nitrile pronucleophiles is described. This simple protocol provides a new approach toward the synthesis of acyclic quaternary carbon stereogenic centers and provides the first example of the direct asymmetric alkylation of a nitrile anion. The synthetic utility of the nitrile products is amply demonstrated through conversion to various functional groups and the synthesis of a bioactive aryl piperazine in an expeditious four-step sequence.

Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.

A one-pot umpolung method for preparation of α-aryl nitriles from α-chloro aldoximes via organocuprate additions to transient nitrosoalkenes

Conjugate addition of a variety of aryl lithiocyanocuprates to nitrosoalkenes generated from α-chloro aldoximes, followed by in situ dehydration of the crude α-aryl aldoxime product with N,N- dicyclohexylcarbodiimide, affords α-aryl nitriles in good overall yields via a one-pot protocol. Georg Thieme Verlag Stuttgart ? New York.

Synthesis of 3,3-and 4,4-alkyl-phenyl-substituted pyrrolidin-2-one derivatives

Syntheses of 3,3-and 4,4-alkyl-phenyl-substituted pyrrolidin-2-one derivatives are described. The final compounds were obtained by the reductive cyclization of relevant cyanoalkanoate esters using NaBH4 and CoCl2.6H2O. The obtained pyrroIidin-2-one derivatives are pharmacophoric fragments for the synthesis of various biologically active compounds.

Phase transfer alkylation of arylacetonitriles revisited

Phase transfer alkylations of phenylacetonitrile derivatives carried out in the presence of 60-75% aqueous KOH, instead of the typical 50% NaOH, provide substantial improvements in the overall yields and purity of products. Reactions with simple secondary alkyl halides, as well as cycloalkylations with 1,2- and 1,3-dihaloalkanes proceed with good yields. Increasing the concentration of base diminishes the formation of by-products from competitive β-elimination processes.