532-28-5

Usage

Uses

1. Used in Chemical Synthesis:
Benzeneacetonitrile, a-hydroxyis used as an intermediate in the synthesis of various organic compounds, particularly for the production of mandeloamide through the action of nitrilase variants.
2. Used in Natural Defense Mechanisms:
In the natural world, Benzeneacetonitrile, a-hydroxyis used by certain insects, such as tiger beetles and an African millipede, as a defense fluid. When these insects expel the fluid, an enzyme catalyzes the conversion of mandelonitrile to benzaldehyde and hydrogen cyanide (HCN), which is usually fatal to the insect's enemy.
3. Used in Pharmaceutical Applications:
Although not explicitly mentioned in the provided materials, Benzeneacetonitrile, a-hydroxycould potentially be used in the pharmaceutical industry as a starting material for the synthesis of various drugs, given its structural properties and reactivity.
4. Used in Extraction Processes:
Benzeneacetonitrile, a-hydroxycan be used in extraction processes to isolate specific compounds, such as mandeloamide, from complex mixtures due to its solubility in alcohol and diethyl ether.

Air & Water Reactions

Mandelonitrile is sensitive to moisture. . Insoluble in water.

Reactivity Profile

Nitriles, such as Mandelonitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Mandelonitrile is combustible.

Safety Profile

Poison by intravenous and subcutaneous routes. Mutation data reported. A severe eye irritant. When heated to decomposition it emits toxic fumes of NOx and CN-. See also NITRILES.

InChI:InChI=1/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H/t8-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 100-52-7 benzaldehyde 
• 74-90-8 hydrogen cyanide 
• 151-50-8 potassium cyanide 
• 29883-15-6 amygdalin 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 613-90-1 benzoyl cyanide 
• 108-24-7 acetic anhydride 
• 99-35-4 1,3,5-trinitrobenzene 
• 7677-24-9 trimethylsilyl cyanide 
• 143-33-9 sodium cyanide 
• 67-64-1 acetone 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 

Downstream Products

• 5766-79-0 2-phenyl-2-piperidinoacetonitrile 
• 4242-46-0 1-cyanobenzyl benzoate 
• 16183-45-2 1-hydroxy-1-phenylbutan-2-one 
• 39531-24-3 5-methyl-3-phenyl-1-benzofuran-2(3H)-one 
• 17064-16-3 2-(benzo[d][1,3]dioxol-5-yl)-5-phenyloxazole 
• 6974-51-2 2-(naphthalen-1-yl)-2-phenylacetonitrile 
• 58258-48-3 2-([1,1′-biphenyl]-4-yl)-2-phenylacetonitrile 
• 41049-36-9 1-hydroxy-1,3-diphenylacetone 
• 6830-78-0 3,6-diphenyl-1,2,4,5-tetrazine 
• 22259-83-2 2-chloro-2-phenylacetonitrile 
• 1088-34-2 3,6-diphenylpyrazin-2(1H)-one 
• 17199-29-0 (S)-Mandelic acid 
• 56946-79-3 bis-(2-chloro-2-phenyl-acetylamino)-phenyl-methane 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 

Relevant academic research and scientific papers

Catalytic asymmetric cyano-phosphorylation of aldehydes using a YLi3tris(binaphthoxide) complex (YLB)

A highly enantioselective cyano-phosphorylation of aldehydes catalyzed by a YLi3tris(binaphthoxide) complex YLB 1 is described. The slow addition of diethyl cyanophosphonate 4 to aldehydes 5 in the presence of YLB 1 (10 mol %), H2O (30 mol %), tris(2,6-dimethoxyphenyl)phosphine oxide 3a (10 mol %), and BuLi (10 mol %) afforded cyanohydrin O-phosphates 6 in up to 98% yield and 97% ee. Mechanistic studies revealed that the addition of cyanide to aldehydes is irreversible and determines the enantioselectivity. The reaction mechanism is also discussed in detail.

Determination of the time course of an enzymatic reaction by 1H NMR spectroscopy: Hydroxynitrile lyase catalysed transhydrocyanation

The time course of the enzyme catalysed transhydrocyanation of benzaldehyde to give (S)-mandelonitrile was investigated using a hydroxynitrile lyase from Hevea brasiliensis as catalyst and acetone cyanohydrin as cyanide donor. Employing special techniques it was possible to apply 1H NMR spectroscopy in aqueous medium to monitor the concentration changes of all substrates and products. By this technique strong evidence for inhibition of the enzyme at higher substrate concentrations was obtained.

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis

Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

Valmet Chiral Schiff-Base Ligands And Their Copper(II) Complexes as Organo, Homogeneous and Heterogeneous Catalysts for Henry, Cyanosilylation and Aldol Coupling Reactions

Cyanosilylation, aldol coupling and asymmetric Henry reactions were carried out with L- and D-valmet ligands in different configurations: i) coordinated to sodium ions, as organocatalysts, with week base properties, ii) complexes with copper(II), as homogeneous catalysts, and iii) immobilized copper(II) complexes onto graphene oxide (GO) as heterogeneous catalysts. For the reaction of benzaldehyde and nitromethane in water these afforded an asymmetric Henry reaction, with a spectacular increase of the conversion and ee (92.5 and 95.8 %, respectively) after the deposition on GO. Ligand complexed copper was also effective for cyanosilylation and Aldol coupling reaction.

Synthesis of Acrylonitriles via Mild Base Promoted Tandem Nucleophilic Substitution-Isomerization of α-Cyanohydrin Methanesulfonates

Main observation and conclusion: We have developed an efficient synthesis of acrylonitriles via mild base promoted tandem nucleophilic substitution-isomerization of α-cyanohydrin methanesulfonates with alkenylboronic acids. This transition metal-free protocol works under simple and mild conditions and offers good chemical yields for a wide range of substrates and demonstrates good functional group tolerance. (Figure presented.).

Constructing a triangular metallacycle with salen-Al and its application to a catalytic cyanosilylation reaction

A triangular metallosalen-based metallacycle was constructed in quantitative yield by the self-assembly of a 180° bis(pyridyl)salen-Al complex and a 60° diplatinum(ii) acceptor in a 1?:?1 stoichiometric ratio. This metallacycle was then successfully used to cyanosilylate a wide range of benzaldehydes with trimethylsilyl cyanide.

Designing of amino functionalized imprinted polymeric resin for enantio-separation of (±)-mandelic acid racemate

S-Mandelic acid (MA) enantio-selective resinous material functionalized with –NH2 groups has been developed and effectively utilized in chiral separation of (±)-MA racemate solution. S-MA has first combined with the polymerizable p-aminophenol and form the corresponding amide derivative, which was then polymerized with phenol/formalin using HCl as a catalyst. The stereo-selective –NH2 functionalized binding sites were then generated within the resin upon the alkaline degradation of the amide linkages followed by acidic treatments that will expel the resin incorporated S-MA out of the polymeric material to get the S-MA imprinted polymer (S-MAPR). The synthesized S-MA chiral amide derivative along with the developed polymeric resin was investigated by various techniques including FTIR and NMR spectra that confirmed the executed chemical modifications. In addition, the morphological appearance of the obtained resins were observed using SEM images. Moreover, the S-MAPR resin was examined to optimize the enantio-selective separation conditions and the studies indicated that the adsorption reached the highest value at pH 7 and the maximum capacity was 243 ± 1 mg/g. In addition, the chiral separation of (±)-MA racemic solution was successfully executed by the S-MAPR separation column with 55% and 82% enantiomeric excess of R- and S-MA within both the initial loading and recovery eluant solutions, respectively.

CO2-Mediated Non-Destructive Cyanide Wastewater Treatment

The facile removal of cyanide anions from cyanide-containing water was achieved using CO2 in conjunction with aldehydes which can be recycled from the process. The conversion of the cyanide ion into an insoluble cyanohydrin in water allowed the removal of cyanide and could be used as a method for treating cyanide contaminated wastewater and for recovering cyanide or cyanohydrins for further applications.

High-yield DL-mandelic acid synthesis process

The invention provides a high-yield DL-mandelic acid synthesis process. The synthesis process specifically comprises the following steps: 1, treating benzaldehyde by using sodium hydrogen sulfite to obtain benzaldehyde sodium hydrogen sulfite; 2, extracting the benzaldehyde sodium hydrogen sulfite by using an organic solvent, recovering unreacted benzaldehyde in the benzaldehyde sodium hydrogen sulfite, and adding sodium cyanide after the extraction is completed to prepare mandelonitrile; 3, adding an inorganic acid, and then carrying out heating and pressure maintaining treatment to hydrolyze the mandelonitrile so as to obtain mandelic acid; and 4, purifying the mandelic acid. According to the method, the step of extracting the p-benzaldehyde sodium hydrogen sulfite salt is added, so that the probability that the product purity is reduced due to benzoin condensation is reduced, the recycled benzaldehyde can be returned to the raw material for use, and the yield can be increased in multiple rounds of reactions; and the hydrolysis process of the mandelonitrile adopts heating and pressure maintaining treatment, so that consumption of inorganic acid can be reduced, and the hydrolysis efficiency is improved.

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.