1885-38-7

Usage

Uses

Used in Corrosion Inhibition:
Cinnamonitrile is a parent compound whose derivatives can be applied as corrosion inhibitors for API J55 steel, providing protection against corrosion and enhancing the durability of the steel.
Used in Pharmaceutical Industry:
Cinnamonitrile is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of various medications.
Used in Perfume Industry:
Cinnamonitrile is utilized as a fragrance ingredient in the perfume industry, adding a warm and spicy scent to various perfumes and fragrances.
Used in Electronic Chemicals:
Cinnamonitrile is employed in the production of electronic chemicals, playing a role in the development and manufacturing of electronic components and materials.

Flavors

Cinnamonitrile is also? known as styrene cyanide, is an excellent synthetic spice,it has a strong spicy aroma like cinnamon and floral nuances, colorless or pale yellow viscous liquid, it is chemically stable, light, heat or acid, alkaline etching can not make it change. There are no toxic side effects on the human body, there is no stimulation in contact with skin ,there are no allergic reactions, compared with cinnamic aldehyde, cinnamonitrile has the stronger ability through the hair, the aroma is strong and lasts for a long time, potential?? skin irritation and toxicity are smaller than? cinnamic aldehyde,it is the ideal substitute for cinnamon oil and cinnamic aldehyde,it can be used in daily chemical flavor formula,it is mainly used for soap flavor and fragrance detergent formulations, the amount is less than 2%. IFRA has no restrictions. Since cinnamonitrile has a unique chemical structure,it can occur Friedel, addition, reduction, hydrolysis reactions,it is also widely be used? in the pharmaceutical, fine chemical industry? . According to the information provided by RIFM, acute toxicity data of cinnamonitrile: oral LD504.15g/kg (rat), skin test LD50> 5g/kg (rabbit). Cinnamonitrile can be made by condensation of acetonitrile with benzaldehyde in the presence of potassium hydroxide solution? ; or it can be made by the? first transformation of cinnamaldehyde? into oxime, then? by the dehydration following.

Antibacterial effects

Nanjing University Department of Biology and the Institute of Hydrobiology of the Chinese Academy of Sciences teachers measured the inhibitory effects of?? plant pathogens Altornaria tenuis Nees and Rhizopus nigricans on their own separate identification , skin addiction germs Epidermophyton floccosum, Trichophytoa gypsoum, Trichophyton rubrum, Microsporum gypseum, as well as 22 kinds of mold (? 18 kinds of common food, fruits and other mold rot fungus, four kinds of human shallow filamentous fungus), the results show that? cinnamonitrile has a high nitrile? antimicrobial effect,it has the role of antibiotics, but? it is not an antibiotic,its mold inhibition effect is good, it has broad? antibacterial spectrum , and anthelmintic effect. Experiments show that the breeding of bacteria in the production process needs folic acid to participate in? , cinnamonitrile? structure is similar to PABA, they are competitive in binding with dihydrofolate synthase, which inhibits the activity of? dihydrofolate synthase, impeding dihydrofolate synthesis, thus affecting the synthesis of folic acid, inhibiting bacterial growth propagation; and it can interfere with the synthesis of some bacteria, and the synthesis of the enzyme needed for cell division to inhibit and impact the synthesis of bacterial RNA , which reduces the permeability of the cell membrane thus affects the normal metabolism of bacteria, resulting in death, so bactericidal effect? are more thorough . What is more amazing? is that the human body does not produce Cinnamonitrile? dependence, it can eliminate bacteria tribes, but it will not break the constraints? relationship between bacteria and thus does not produce resistance. Cinnamonitrile? itself is a spice, there are no toxic side effects on the human body, in contact with skin no stimulation, no allergic reactions. Experts said excitedly,that with deepening study of the cinnamonitrile? antibacterial? aspect? , cinnamonitrile is expected to completely replace antibiotics, and become the "Terminator"of antibiotics.

Preparation

Cinnamic aldehyde reacts with hydroxylamine hydrochloride in the presence of pyridine by the addition-elimination reaction to produce aldehyde oxime, then it boils with toluene azeotropic and after dehydration to generate? cinnamonitrile.

Preparation

From styryl bromide and potassium cyanide (Arctander, 1969).

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 6340, 1959 DOI: 10.1021/ja01532a069Tetrahedron Letters, 21, p. 2161, 1980 DOI: 10.1016/S0040-4039(00)78986-6

Toxicity evaluation

The acute oral LD50 value in rats was reported as 4.15g/kg (3.67-4.63 g/kg) and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Moreno, 1974). In rabbits, iv injection of cinnamyl nitrile (20.3 mg/kg) caused death in 10 min. In guinea-pigs and rabbits, cinnamyl nitrile was found to produce the same effects as hydrogen cyanide, with almost equal toxicity, and rabbits given doses higher than the lethal dose were found to die almost as rapidly as those given hydrogen cyanide (Hunt, 1923).

Flammability and Explosibility

Notclassified

Metabolism

The toxicity of organic cyanides appears to depend almost entirely on whether they can be metabolized in the body to the free cyanide ion, and on the rate and extent of this conversion and the rate of detoxication of cyanide to thiocyanate. In general, alkyl and arylalkyl cyanides are metabolized with the formation of hydrogen cyanide, while the nitrile group of aryl cyanides is relatively stable. The high toxicity of iv-administered cinnamyl nitrile and the rapidity of death suggest that in rabbits Cinnamonitrile is metabolically converted to hydrogen cyanide (Hunt, 1923; Williams, 1959).

InChI:InChI=1/C9H7N/c10-8-4-7-9-5-2-1-3-6-9/h1-7H/b7-4-

Upstream product

• 110-86-1 pyridine 
• 14378-06-4 (E)-α-cyanocinnamic acid 
• 100-52-7 benzaldehyde 
• 372-09-8 cyanoacetic acid 
• 14371-10-9 (E)-3-phenylpropenal 
• 684-78-6 O,N-bis-(trifluoroacetyl)-hydroxylamine 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 621-79-4 cinnamamide 
• 13181-39-0 O-(2.4-dinitro-phenyl)-β-cinnamaldoxime 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 588-73-8 (Z)-β-bromostyrene 
• 544-92-3 copper(I) cyanide 
• 151-50-8 potassium cyanide 

Downstream Products

• 10199-68-5 4-phenyl-1H-pyrazole 
• 65993-16-0 trans-cinnamic acid tert-pentylamide 
• 38172-04-2 3-fluoren-9-yl-3-phenyl-propionitrile 
• 100710-33-6 2-methyl-6-phenyl-cyclohex-3-enecarbonitrile 
• 108719-02-4 2,5-dimethyl-6-phenyl-cyclohex-3-enecarbonitrile 
• 71103-79-2 1,3,5,8-tetraphenyl-2,6-diaza-bicyclo[2.2.2]oct-2-ene 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 14371-10-9 (E)-3-phenylpropenal 
• 2286-54-6 3,3-diphenyl-propionitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 621-79-4 cinnamamide 
• 55978-61-5 styrylamidine 
• 19521-13-2 (+/-)-2r_F,3c_F-dibromo-3cat_F-phenyl-propionitrile 
• 98994-42-4 3,3-dichloro-2-(α-hydroxy-benzyl)-acrylonitrile 

Relevant academic research and scientific papers

Thermolysis of 1-phthalimidoaziridine-2-carbonitriles in the presence of dipolarophiles

Thermolysis of trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile and trans-1-phthalimidoaziridine-2,3-dicarbonitrile in the presence of several dipolarophiles involves 1,3-dipolar cycloaddition to intermediate azomethine ylides and leads to 1-phthalimidopyrrolidine derivatives with good yields and high stereoselectivity. Thermally induced opening of the three-membered ring in trans-2,3-disubstituted 1-phthalimidoaziridines occurs in conrotatory mode to produce the corresponding cis-azomethine ylides in keeping with the orbital symmetry conservation rules. The relative configuration of substituents in the dipolarophiles is retained, which implies concerted mechanism of the addition.

An efficient and practical synthesis of diphenyl cyanomethylenephosphonate: Applications to the stereoselective synthesis of cis-α,β-unsaturated nitriles

Diphenyl cyanomethylenephosphonate (PhO)2POCH2CN was prepared as a stable crystalline solid in high yield in a single step from acetonitrile, LDA, and (PhO)2P(O)CI. The potassium ylide generated from this compound afforded α,β-unsaturated nitriles upon reacting with aldehydes, with a stereoselectivity of 64-100% favoring the cis-isomer.

Novel innovation systems for a cellular approach to continuous process chemistry from discovery to market

Continuous processing of liquid/liquid synthesis and microreaction technology are shown to reduce the cost of process development and manufacturing of active pharmaceutical ingredients and other functional molecules on a commercial scale. Combinatorial synthesis systems for continuous chemistry are introduced, and their applications are described. Reactions within these systems scale seamlessly in standardized commercial continuous synthesis equipment allowing rapid access to kilogram quantities of advanced intermediates. Chemical and process development within such systems are illustrated by a case study of a continuous multistep process. Additionally, another case study shows the benefit of microreaction technology in the manufacture of high value added functional chemicals.

Palladium/magnesium-lanthanum mixed oxide catalyst in the heck reaction

A new, reusable palladium/magnesium-lanthanum mixed oxide catalyst has been found to exhibit unprecedented high catalytic activity and selectivity for the heterogeneous Heck cross-coupling reaction of aryl halides with alkenes. The nature of the aryl halides has a determinate effect on the reaction yield. The corresponding reactions of a wide range of activated and non-activated aryl bromides and chlorides furnished the arylated product with high E/Z isomer ratios even already at 80°C. The stereoselectivity depended on the nature of the olefins.

Synthesis of nitriles from aldoximes using silica gel as catalyst under microwave irradiation

A rapid and efficient synthesis of nitriles via dehydration from the corresponding aldoximes has been carried out in the presence of Silica gel as catalyst under microwave irradiation in 83-95% yield.

STEREOSELECTIVE CARBONYL OLEFINATION VIA ORGANOSILICON COMPOUNDS. BORON AND TITANIUM REAGENTS

Boron reagents derived from trialkylsilylacetonitriles are effective for the synthesis of Z-α,β-unsaturated nitriles.Z-Terminal enyne units are synthesized from the titanium reagent from 1,3-bis-(trimethylsilyl)propyne and aldehydes.

N-(2,3,5,6-tetrachloropyrid-4-yl)cinnamide

The title compound, C14H8Cl4N2O, is an unexpected side product of a reaction to convert an acid chloride into a nitrile, the nature of which indicates the probable mechanism of the major reaction. In the crystal structure, a conjugated and approximately planar cinnamide framework is attached to an almost perpendicular tetrachloro-substituted pyridyl ring, severe steric interactions overcoming the enhanced delocalization which would occur with coplanarity.

Azole Based Acetohydrazide Derivatives of Cinnamaldehyde Target and Kill Candida albicans by Causing Cellular Apoptosis

Opportunistic fungal pathogens including Candida albicans are responsible for the alarming rise in hospital acquired infections and millions of deaths worldwide. The current treatment modalities are not enough to handle this situation, and therefore, new treatment modalities and strategies are desperately needed. In this direction, we synthesized a series of azole based acetohydrazide derivatives of cinnamaldehyde and subjected it to antifungal activity evaluation. Preliminary antifungal activity evaluation revealed tremendous antifungal potential of some of the derivatives against fluconazole susceptible and resistant clinical isolates of Candida albicans. Although all the compounds in the series are structurally similar except for the presence of different substituents on the phenyl ring of the acetohydrazide pendent, they sharply differed in their activity profile. Further mechanism of action studies revealed that these compounds have an apoptotic effect on C. albicans confirmed via Annexin V-FITC staining and TUNEL assay.

Transformation of aldehydes into nitriles in an aqueous medium using O-phenylhydroxylamine as the nitrogen source

The conversion of an aldehyde into a nitrile can be efficiently performed using O-phenylhydroxylamine hydrochloride in buffered aqueous solutions. The reported method is specifically optimized for aqueous-soluble substrates including carbohydrates. Several reducing sugars including monosaccharides, disaccharides, and silyl-protected saccharides were transformed into cyanohydrins in high yields. The reaction conditions are also suitable for the formation of nitriles from various types of hydrophobic aldehyde substrates. Furthermore, cyanide can be eliminated from cyanohydrins, analogous to the Wohl degradation, by utilizing a readily-removed weakly basic resin as a promoter.

Method for dehydrating primary amide into nitriles under catalysis of cobalt

The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.