4111-08-4

Usage

Uses

Used in Chemical Synthesis:
2-Hydroxy-2-methylbutanenitrile is used as an intermediate in the chemical synthesis of various compounds, particularly in the pharmaceutical and agrochemical industries. Its unique structure allows for the creation of a wide range of derivatives, making it a valuable building block for the development of new molecules with potential applications in these fields.
Used in Flavor and Fragrance Industry:
2-Hydroxy-2-methylbutanenitrile is used as a building block for the synthesis of various flavor and fragrance compounds. Its unique chemical structure contributes to the creation of novel scents and flavors, enhancing the sensory experience in the perfumery and food industries.
Used in Polymer Industry:
In the polymer industry, 2-hydroxy-2-methylbutanenitrile is used as a monomer for the production of specialty polymers with specific properties. Its incorporation into polymer chains can lead to materials with enhanced mechanical, thermal, or chemical resistance, depending on the desired application.
Used in Pharmaceutical Industry:
2-Hydroxy-2-methylbutanenitrile is used as a starting material for the synthesis of various pharmaceutical compounds, including drugs with potential therapeutic applications. Its unique structure allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical industry, 2-hydroxy-2-methylbutanenitrile is used as a precursor for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique chemical properties enable the development of more effective and environmentally friendly products for agricultural use.

InChI:InChI=1/C5H9NO/c1-3-5(2,7)4-6/h7H,3H2,1-2H3

Upstream product

• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 78-93-3 butanone 
• 25438-34-0 2-Methyl-2-trimethylsilanyloxy-butyronitrile 
• 623-26-7 terephthalonitrile 
• 110-83-8 cyclohexene 
• 7677-24-9 trimethylsilyl cyanide 
• 151-50-8 potassium cyanide 
• 143-33-9 sodium cyanide 
• 75-16-1 methylmagnesium bromide 
• 74-90-8 hydrogen cyanide 

Downstream Products

• 77-70-3 α-hydroxy-α-methylbutyric acid ethyl ester 
• 6622-76-0 methyl (E)-2-methyl-2-butenoate 
• 1112-12-5 α-methyl-α-hydroxybutyramide 
• 471-46-5 Oxalamide 
• 74-90-8 hydrogen cyanide 
• 20068-02-4 (Z)-2-methyl-2-butenenitrile 
• 30574-97-1 tiglonitrile 
• 1647-11-6 2-ethyl-acrylonitrile 
• 25438-34-0 2-Methyl-2-trimethylsilanyloxy-butyronitrile 
• 5953-76-4 methyl angelate 
• 37505-07-0 (S)-2-hydroxy-2-methylbutyric acid 
• 37505-02-5 (R)-(-)-2-hydroxy-2-methylbutyric acid 
• 20047-49-8 (Z)-2-methyl-1-phenyl-2-buten-1-one 
• 20047-50-1 (E)-2-methyl-1-phenyl-2-buten-1-one 

Relevant academic research and scientific papers

Insights into the Mechanism of an Allylic Arylation Reaction via Photoredox-Coupled Hydrogen Atom Transfer

Despite widespread use as a synthetic method, the precise mechanism and kinetics of photoredox coupled hydrogen atom transfer (HAT) reactions remain poorly understood. This results from a lack of detailed kinetic information as well as the identification of side reactions and products. In this report, a mechanistic study of a prototypical tandem photoredox/HAT reaction coupling cyclohexene and 1,4-dicyanobenzene (DCB) using an Ir(ppy)3 photocatalyst and thiol HAT catalyst is reported. Through a combination of electrochemical, photochemical, and spectroscopic measurements, key unproductive pathways and side products are identified and rate constants for the main chemical steps are extracted. The reaction quantum yield was found to decline rapidly over the course of the reaction. An unreported cyanohydrin side product was identified and thought to play a key role as a proton acceptor in the reaction. Transient absorption spectroscopy (TAS) and quantum chemical calculations suggested a reaction mechanism that involves radical addition of the nucleophilic DCB radical anion to cyclohexene, with cooperative HAT occurring as the final step to regenerate the alkene. Kinetic modeling of the reaction, using rate constants derived from TAS, demonstrates that the efficiency of the reaction is limited by parasitic absorption and unproductive quenching between excited Ir(ppy)3 and the cyanohydrin photoproduct.

Catalytic Transfer Hydration of Cyanohydrins to α-Hydroxyamides

We report the palladium(II)-catalyzed transfer hydration of cyanohydrins to α-hydroxyamides by using carboxamides as water donors. This method enables selective hydration of various aldehyde- and ketone-derived cyanohydrins to afford α-mono- and α,α-disubstituted-α-hydroxyamides, respectively, under mild conditions (50 °C, 10 min). The direct conversion of fenofibrate, a drug bearing a benzophenone moiety, into a functionalized α,α-diaryl-α-hydroxyamide was achieved by means of a hydrocyanation-transfer hydration sequence. Preliminary kinetic studies and the synthesis of a site-specifically 18O-labeled α-hydroxyamide demonstrated the carbonyl oxygen transfer from the carboxamide reagent into the α-hydroxyamide product.

A single-step, mild, neutral, catalyst-free method for cyanohydrin synthesis

A wide variety of carbonyl compounds can be transformed to their corresponding cyanohydrins in a single step using a dimethyl sulfoxide (DMSO)-water system in excellent yields (75-94%). The major advantages of this system are that the reaction conditions are mild and neutral; the reaction proceeds without catalyst and gives the corresponding cyanohydrins in short time (15-120 min).

BIOFILM CONTROL

Compositions and methods suitable for killing bacteria and controlling biofilms comprising one or more microorganisms are provided wherein molecules capable of emulating cell-to-cell signal molecules of the microorganisms are utilized.

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).

Method for making ethyl ketone cyanohydrin

This process for the production of the methyl ethyl ketone cyanohydrin of formula (I) is characterized by the fact that hydrocyanic acid and methyl ethyl ketone are reacted in the presence of diethylamine as a catalyst.

Studies on phosphoroheterocycle chemistry III: An unusual way to 1,3,2-thiazaphospholidine-4-thione 2-sulfide derivatives

An unusual but efficient method for the synthesis of phosphoroheterocycles, 1,3,2-thiazaphospholidine-4-thione 2-sulfide derivatives, by the reaction of Lawesson's reagent with a variety of α-hydroxy nitriles has been developed. The possible mechanism of the reaction is proposed to involve thiation of hydroxy group in a first step, sequential addition of P-SH to the nitrile and rearrangement resulting in the title phosphoroheterocycles. The preliminary bioassays show that these heterocyclic compounds have herbicidal properties.

Naturally occurring cyanohydrins, analogues and derivatives as potential insecticides

Several naturally occurring cyanohydrins were tested for fumigation toxicity to two insect species, the house fly (Musca domestica L) and the lesser grain borer (Rhyzopertha dominica (F)). Synthetic analogues of these compounds were tested as well. Most of the cyanohydrins tested were more toxic as fumigants to M domestica and R dominica than chloropicrin; some compounds were nearly as toxic as dichlorvos. Naturally occurring cyanohydrins were among the most toxic tested. (C) 2000 Society of Chemical Industry.

KINETIC RESOLUTION OF KETONE CYANOHYDRIN ACETATES WITH A MICROBIAL ENZYME

Incubation of dl-1-cyano-1-metylalkyl (or alkenyl) acatates (methyl ketone cyanohydrin acetates) with cells of Pichia miso IAM 4682 afforded optically active acetates and the corresponding ketones via asymmetric hydrolysis.Resulting (S)-2-cyano-2-undecyl acetate was converted to the aminofuranone derivative without losing its optical purity.

Process for preparation of cyanohydrins

This invention relates to the discovery that high yields of excellent quality cyanohydrins can be prepared by reacting certain carbonyl compounds in a solution of metallic cyanide and hydrochloric acid.