54089-83-7

Usage

Uses

Used in Pharmaceutical Industry:
3-methyl-5-phenylpentanenitrile is used as a synthetic intermediate for the production of various pharmaceuticals. Its versatile reactivity and ability to undergo a variety of chemical reactions make it a valuable compound in the development of new drugs.
Used in Agrochemical Industry:
3-methyl-5-phenylpentanenitrile is used as a building block in the synthesis of agrochemicals. Its properties allow for the creation of compounds that can be used in the development of pesticides, herbicides, and other agricultural products.
Used in Fragrance Industry:
3-methyl-5-phenylpentanenitrile is used as a component in the creation of fragrances. Its unique chemical structure contributes to the development of new and complex scents for use in perfumes, colognes, and other scented products.
It is important to handle 3-methyl-5-phenylpentanenitrile with care, as it can cause irritation to the skin, eyes, and respiratory system if not properly managed. Overall, 3-methyl-5-phenylpentanenitrile is a valuable and versatile compound with a wide range of applications in the chemical industry.

InChI:InChI=1/C12H15N/c1-11(9-10-13)7-8-12-5-3-2-4-6-12/h2-6,11H,7-9H2,1H3

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 105-34-0 methyl 2-cyanoacetate 
• 2344-70-9 1-phenyl-3-butanol 
• 75-05-8 acetonitrile 
• 4786-20-3 crotononitrile 
• 17376-04-4 2-phenethyl iodide 
• 93893-89-1 3-methyl-5-phenylpent-2-enenitrile 
• 97764-02-8 3-Methyl-4-nitro-5-phenyl-pentanenitrile 
• 6125-24-2 2-Phenylnitroethane 

Downstream Products

• 63223-28-9 (5-Hydroxy-6-methoxy-3-methylhexyl)benzol 
• 63223-31-4 1-Methoxy-4-methyl-6-phenylhexanon-2 

Relevant academic research and scientific papers

Formal reductive addition of acetonitrile to aldehydes and ketones

An efficient and highly productive rhodium-catalyzed method for the synthesis of nitriles employing aldehydes or ketones, methyl cyanoacetate, water and carbon monoxide as starting materials has been developed. Simple rhodium chloride without any ligands can be used. The fine tuning of the substrate can lead to the activity higher than 5000 TON.

Asymmetric hydrogenation of α,β-unsaturated nitriles with base-activated iridium N,P ligand complexes

Although many chiral catalysts are known that allow highly enantioselective hydrogenation of a wide range of olefins, no suitable catalysts for the asymmetric hydrogenation of α,β-unsaturated nitriles have been reported so far. We have found that Ir N,P ligand complexes, which under normal conditions do not show any reactivity towards α,β-unsaturated nitriles, become highly active catalysts upon addition of N,N- diisopropylethylamine. The base-activated catalysts enable conjugate reduction of α,β-unsaturated nitriles with H2 at low catalyst loadings, affording the corresponding saturated nitriles with high conversion and excellent enantioselectivity. In contrast, alkenes lacking a conjugated cyano group do not react under these conditions, making it possible to selectively reduce the conjugated C=C bond of an α,β-unsaturated nitrile, while leaving other types of C=C bonds in the molecule intact.

Iridium-catalyzed α-alkylation of acetonitrile with primary and secondary alcohols

Acetonitrile is successfully alkylated with primary and secondary alcohols in the presence of t-BuOK using [Ir(OH)- (cod)]2 as a catalyst. This method provides a very clean and atom-economical convenient direct route to substituted nitriles, which are very important raw materials in organic and industrial chemistry.

A New Coupling Reaction of Alkyl Iodides with Electron Deficient Alkenes Nickel Boride (cat.) - Borohydride Exchange Resin in Methanol

The radical addition reaction of alkyl iodides with α,β-unsaturated esters, nitriles, and ketones proceeds in moderate to excellent yields (50-95%) using Ni(OAc)2 (0.05-0.2 equiv) - BER (3-5 equiv) in methanol in 1-9 h at room temperature or at 65°C. Nickel boride on borohydride exchange resin (BER) is a good alternative reagent to tributyltin hydride for the coupling of alkyl iodides with the electron deficient alkenes in methanol. Compared with tributyltin hydride method, this method has an advantage of simple workup, since nickel boride - BER can be removed readily by filtration.

Two-Carbon Elongation/Annulation of Alcohols to Nitriles

Alcohols were replaced by a two-carbon nitrile unit in good to excellent yields via dehydrative alkylation with (phenylsulfonyl)acetonitrile under modified Mitsunobu conditions followed by desulfonylation using magnesium.Diols and haloalcohols furnished cycloalkylnitriles.

New Synthetic Methods. Conjugate Addition of Alkyl Groups to Electron Deficient Olefins with Nitroalkanes as Alkyl Anion Equivalents

The sequence of the Michael addition of nitroalkanes and denitration from the adduct provides a new and general method for conjugate addition of primary and secondary alkyl groups to electron deficient olefins such as α,β-unsaturated aldehydes, ketones, esters, nitriles, sulfoxides, and sulfones.