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Cas Database

140-29-4

140-29-4

Identification

  • Product Name:Benzyl cyanide

  • CAS Number: 140-29-4

  • EINECS:205-410-5

  • Molecular Weight:117.15

  • Molecular Formula: C8H7N

  • HS Code:2837.19 Oral rat LD50: 270 mg/kg

  • Mol File:140-29-4.mol

Synonyms:Acetonitrile,phenyl- (6CI,7CI,8CI);(Cyanomethyl)benzene;2-Phenylacetonitrile;2-Phenylethanenitrile;Phenylacetonitrile;

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Safety information and MSDS view more

  • Pictogram(s):VeryT+,ToxicT

  • Hazard Codes:T+,T

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H330 Fatal if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Poisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes. (EPA, 1998)

  • Fire-fighting measures: Suitable extinguishing media Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. Small fires: dry chemical, carbon dioxide, water spray, or foam. Large fires: water spray, fog, or foam. Move container from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. (EPA, 1998) When heated to decomposition, it emits very toxic fumes of cyanide and nitrogen oxides. Container may explode in heat of fire. Runoff from fire control water may give off poisonous gases. Avoid sodium hypochlorite. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 383 Articles be found

Microwave-assisted dehydration and chlorination using phosphonium salt

Tanji, Ken-Ichi,Koshio, Jiro,Sugimoto, Osamu

, p. 1983 - 1987 (2005)

Microwave-assisted reaction using phosphonium salt for dehydration of primary amides and chlorination of hydroxyheteroaromatics was carried out. Copyright Taylor & Francis, Inc.

New Methods and Reagents in Organic Synthesis; 6. A Simple One-Pot Conversion of Primary Alcohols to Nitriles having One C-Atom more

Mizuno, Akira,Hamada, Yasumasa,Shioiri, Takayuki

, p. 1007 - 1009 (1980)

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A convenient preparation of alkyl nitriles by the Mitsunobu procedure

Wilk

, p. 2481 - 2484 (1993)

A convenient preparation of alkyl nitriles from alcohols extending the use of the Mitsunobu reaction is described. Acetone cyanohydrin is the acidic component and the source of cyanide ion.

Kinetic studies on the catalytic synthesis of benzyl cyanide from 2-phenylethanol and ammonia

Takeuchi,Miwa,Okada

, p. 2637 - 2641 (1980)

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Construction of enantioenriched polysubstituted hexahydropyridazines via a sequential multicatalytic process merging palladium catalysis and aminocatalysis

Marques,Giardinetti,Marrot,Coeffard,Moreau,Greck

, p. 2828 - 2832 (2016)

An efficient multicatalytic strategy for the construction of nitrogen-containing heterocycles has been reported. The powerful combination of organic and metal catalysis in a single vessel allowed the formation of enantioenriched polysubstituted cyclic 6-membered hydrazines bearing a quaternary stereocenter in good yields and selectivities.

Switch of reaction pathway induced by solid support and ultrasound

Doan, Tan L.H.,Le, Thach N.

, p. 337 - 340 (2012)

The influence of activation methods and solid support on the reaction course of benzyl bromide, KCN, and toluene has been investigated. When KCN is not supported on alumina, the reaction under the mechanical agitation follows the aromatic electrophilic substitution pathway, while the reaction under sonication follows nucleophilic substitution. However, when KCN supported on alumina is employed, only the nucleophilic substitution product is obtained under both ultrasound and mechanical agitation. Copyright Taylor & Francis Group, LLC.

-

Shvartsberg et al.

, (1976)

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A New Synthesis of α-Phenylhomoallylnitriles from β-Nitrostyrene and Allylic Silanes

Uno, Hidemitsu,Fujiki, Satomi,Suzuki, Hitomi

, p. 1267 - 1268 (1986)

TiCl4-catalyzed addition of allylic silanes to β-nitrostyrene affords γ,δ-unsaturated nitronates which, on treatment with low valent titanium in situ generated from Ti(IV) and zinc, are smoothly converted to γ,δ-unsaturated nitriles in moderate yields.

Nucleophilic Substitution Reaction of Alkyl Halide by Anion on a Macroporous Polymer Resin

Sukata, Kazuaki

, p. 4388 - 4390 (1985)

-

-

Glass et al.

, p. 1546 (1971)

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Polycationic (Mixed) Core-Shell Dendrimers for Binding and Delivery of Inorganic/Organic Substrates

Kleij, Arjan W.,Coevering, Rob van de,Gebbink, Robertus J. M. Klein,Noordman, Anne-Marie,Spek, Anthony L.,Koten, Gerard van

, p. 181 - 192 (2001)

The convergent synthesis of a series of polycationic aryl ether dendrimers has been accomplished by a convenient procedure involving quantitative quaternarization of aryl(poly)amine core molecules. The series has been expanded to the preparation of the first polycationic, mixed core-shell dendrimer. All these dendrimers consist of an apolar core with a peripheral ionic layer which is surrounded by a less polar layer of dendritic wedges. These cationic, macromolecular species have been investigated for their ability to form assemblies with (anionic) guest molecules. The results obtained from UV/Vis and NMR spectroscopies, and MALDI-TOF-MS demonstrate that all the cationic sites throughout the dendrimer core are involved in ion pair formation with anionic guests giving predefined guest/host ratios up to 24. The large NMR spectroscopic shifts of resonances correlated with the groupings located in the core of the dendrimers, together with the relaxation time data indicate that the anionic guests are associated with the cationic core of these dendrimers. The X-ray molecular structure of the octacationic, tetra-arylsilane model derivative [Si(C6H3{CH2NMe3}2-3,5)4](8+) * 8I(-) shows that the iodide counterions are primarily located near the polycationic sphere. The new polycationic dendrimers have been investigated for their catalytic phase-transfer behavior and substrate delivery over a nanofiltration membrane.

-

Isomura et al.

, p. 3499 (1968)

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Ionic liquids as catalytic green solvents for nucleophilic displacement reactions

Wheeler,West,Liotta,Eckert

, p. 887 - 888 (2001)

We demonstrate the use of room-temperature ionic liquids as a catalytic, environmentally benign solvent for the cyanide displacement on benzyl chloride, replacing phase-transfer catalyzed biphasic systems and thus eliminating the need for a volatile organic solvent and hazardous catalyst disposal.

Bartmess et al.

, p. 6046,6049,6053 (1979)

The hydrogenation of mandelonitrile over a Pd/C catalyst: Towards a mechanistic understanding

McAllister, Mairi I.,Boulho, Cédric,McMillan, Liam,Gilpin, Lauren F.,Brennan, Colin,Lennon, David

, p. 26116 - 26125 (2019)

A carbon supported Pd catalyst is used in the liquid phase hydrogenation of the aromatic cyanohydrin mandelonitrile (C6H5CH(OH)CH2CN) to afford the primary amine phenethylamine (C6H5CH2CH2NH2). Employing a batch reactor, the desired primary amine is produced in 87% selectivity at reaction completion. Detection of the by-product 2-amino-1-phenylethanol (C6H5CH(OH)CH2NH2) accounts for the remaining 13% and closes the mass balance. The reaction mechanism is investigated, with a role for both hydrogenation and hydrogenolysis processes established.

BENZYLGLUCOSINOLATE DEGRADATION IN HEAT-TREATED LEPIDIUM SATIVUM SEEDS AND DETECTION OF A THIOCYANATE-FORMING FACTOR

Hasapis, Xenophon,MacLeod, Alexander J.

, p. 1009 - 1014 (1982)

Lepidium sativum seeds were dry heated at 125 deg C for varying periods, and also for 30 min at various temperatures.Autolysates were then analysed for benzylglucosinolate degradation products.Whilst heating for 4 hr 20 min at 125 deg C was sufficient to prevent formation of benzyl thiocyanate, just over 7.5 hr at 125 deg C was required before benzyl isothiocyanate also ceased to be produced.This indicates the presence of a discrete, thiocyanate-forming factor in L. sativum seeds, separate from thioglucosidase.After 7.5 hr at 125 deg C, benzyl cyanide continued to be formed, proving that it can be obtained (in relatively small amounts) directly from the glucosinolate even without the influence of any thioglucosidase.In general, isothiocyanate was the more favoured product of glucosinolate degradation following heat treatment of seeds, until the point of thioglucosidase inactivation was approached when nitrile formation took over.It is suggested that the thiocyanate-forming-factor is an isomerase causing Z-E isomerization of the glucosinolate aglucone, but that only those glucosinolates capable of forming particularly stable cations are then able to undergo E-aglucone rearrangement to thiocyanate. Key Word Index- Lepidium sativum; Cruciferae; cress; glucosinolate degradation; thiocyanate.

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Vaughan,McCane

, p. 2504 (1954)

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Supported Cyanides: The Interaction of Potassium Cyanide with High Surface Area Inorganic Support Materials and the Development of Highly Reactive Cyanide Reagents

Clark, James H.,Duke, Catherine V. A.

, p. 1330 - 1332 (1985)

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HPLC-based kinetics assay facilitates analysis of systems with multiple reaction products and thermal enzyme denaturation

Klingaman, Chase A.,Wagner, Matthew J.,Brown, Justin R.,Klecker, John B.,Pauley, Ethan H.,Noldner, Colin J.,Mays, Jared R.

, p. 37 - 47 (2017)

Glucosinolates are plant secondary metabolites abundant in Brassica vegetables that are substrates for the enzyme myrosinase, a thioglucoside hydrolase. Enzyme-mediated hydrolysis of glucosinolates forms several organic products, including isothiocyanates (ITCs) that have been explored for their beneficial effects in humans. Myrosinase has been shown to be tolerant of non-natural glucosinolates, such as 2,2-diphenylethyl glucosinolate, and can facilitate their conversion to non-natural ITCs, some of which are leads for drug development. An HPLC-based method capable of analyzing this transformation for non-natural systems has been described. This current study describes (1) the Michaelis–Menten characterization of 2,2-diphenyethyl glucosinolate and (2) a parallel evaluation of this analogue and the natural analogue glucotropaeolin to evaluate effects of pH and temperature on rates of hydrolysis and product(s) formed. Methods described in this study provide the ability to simultaneously and independently analyze the kinetics of multiple reaction components. An unintended outcome of this work was the development of a modified Lambert W(x) which includes a parameter to account for the thermal denaturation of enzyme. The results of this study demonstrate that the action of Sinapis alba myrosinase on natural and non-natural glucosinolates is consistent under the explored range of experimental conditions and in relation to previous accounts.

Passflow syntheses using functionalized monolithic polymer/glass composites in flow-through microreactors

Kirschning, Andreas,Altwicker, Carsten,Drger, Gerald,Harders, Jan,Hoffmann, Nora,Hoffmann, Ulrich,Schnfeld, Hagen,Solodenko, Wladimir,Kunz, Ulrich

, p. 3995 - 3998 (2001)

A chemist's wish finally becomes reality: microreactors for every synthetic laboratory! By precipitation polymerization various polymers are introduced into the irregular pore system of a porous glass rod. By embedding these rods into a housing, followed by functionalization and immobilization of reagents onto the polymer phase, versatile microreactors are obtained. With this apparatus, chemical transformations in solution can be performed, for example, a steroid derivatization (see picture).

Calixarene ionic liquids: Excellent phase transfer catalysts for nucleophilic substitution reaction in water

Yang, Fafu,Guo, Hongyu,Jiao, Ziyu,Li, Congcong,Ye, Jinqi

, p. 327 - 332 (2012)

The first examples of calixarene ionic liquids 3 and 6 with 3D-shaped cavities were obtained in high yields by reacting calix[4]arene or thiacalix[4]arene with 1,6-dibromohexane and then refluxing in 1-methylimidazole. The experiments of phase transfer catalysis in water suggested that they possessed excellent catalytic properties of aromatic nucleophilic substitution reaction and benzyl nucleophilic substitution. The optimized yields of product in catalytic reaction were as high as approximate 97% under mild reaction conditions. The cavities of calixarene skeleton played the crucial roles in catalysis and the stable cone conformation was favorable for catalysis.

The reduction of α,β-unsaturated nitriles and α-halonitriles with sodium hydrogen telluride

Blay, Gonzalo,Cardona, Luz,Garcia, Begona,Lahoz, Luisa,Pedro, Jose R.

, p. 8611 - 8618 (1996)

Sodium hydrogen telluride reacts chemoselectively with α,β- unsaturated nitriles and α-halonitriles linked to aromatic and aliphatic substituents to corresponding saturated nitriles with good yields.

Polymer-Supported Reagents: The Use of Polymer-Supported Cyanide and Thiocyanate to Prepare Nitriles, Thiocyanates, and Isothiocyanates

Harrison, Charles R.,Hodge, Philip

, p. 299 - 301 (1980)

-

-

Smolinsky,G.,Feuer,B.I.

, p. 3882 - 3884 (1966)

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A poly(ethylene glycol)-supported quaternary ammonium salt: An efficient, recoverable, and recyclable phase-transfer catalyst

Annunziata, Rita,Benaglia, Maurizio,Cinquini, Mauro,Cozzi, Franco,Tocco, Graziella

, p. 1737 - 1739 (2000)

(matrix presented) A quaternary ammonium salt readily immobilized on a soluble poly(ethylene glycol) polymer support efficiently catalyzes different reactions carried out under phase-transfer catalysis conditions; the catalyst, easily recovered by precipitation and filtration, shows no appreciable loss of activity when recycled three times.

Mechanisms of Polymer-Supported Catalysis. 2. Reaction of Benzyl Bromide with Aqueous Sodium Cyanide Catalyzed by Polystyrene-Bound Onium Ions

Tomoi, M.,Ford, Warren T.

, p. 3828 - 3832 (1981)

Rates of reaction of benzyl bromide in toluene with aqueous sodium cyanide in triphase mixtures with polystyrene-supported benzyltrimethylammonium and benzyltri-n-butylphosphonium ions as phase-transfer catalysts depend upon mechanical stirring speed, catalyst particle size, and percent of cross-linking of the polymer support.Increases in stirring speed increase reaction rates up to a maximum at about 600 rpm.Decreases in particle size increase reaction rates.Increases in polymer cross-linking decrease reaction rates.Apparent activation energies with benzyltrimethylammoniumion catalyst are 12 - 15 kcal/mol at 70 - 90 deg C.Rates of reaction of benzyl bromide, benzyl chloride, 1-bromooctane, and 1-bromohexadecane all are affected differently by variations in catalyst structure, particle size, and cross-linking.The results are discussed in terms of mass transfer, intraparticle diffusion, and intrinsic reactivity limitations on reaction rates.Slow intraparticle diffusion reduces the reactivity differences between benzyl bromide and 1-bromooctane and between benzyl bromide and benzyl chloride and causes 1-bromohexadecane to react much slower than 1-bromooctane.

EFFECTS OF METAL IONS ON BENZYLGLUCOSINOLATE DEGRADATION IN LEPIDIUM SATIVUM SEED AUTOLYSATES

Hasapis, Xenophon,MacLeod, Alexander J.

, p. 559 - 564 (1982)

The effects of varying concentrations of Fe2+ (5E-5 - 5E-1 M) on benzylglucosinolate degradation in Lepidium sativum seed autolysates were investigated.Increased glucosinolate decomposition was observed over the whole range with a maximum effect at ca. 6E-3 M Fe2+, at which point glucosinolate degradation was more than three times that obtained in the absence of added Fe2+.Nitrile formation was especially enhanced in the presence of all concentrations of Fe2+ studied, and maximum amounts were obtained at ca. 6E-3 M Fe2+, when a more than four-fold increase over quantities produced in the absence of Fe2+ was observed.Thiocyanate formation was also promoted with a maximum at ca. 4E-3 M Fe2+, but isothiocyanate production was considerably reduced in all cases.It is suggested that Fe2+ inhibits isothiocyanate formation by interfering with the availability of ascorbic acid which is a proven co-factor for most thioglucosidase isoenzymes, but that an Fe2+-ascorbate complex might then be responsible for promoting enzymic production of nitrile.The effects of a limited range of concentrations of Fe3+ and Cu+ were also studied, and results related to those for Fe2+ The relevance of the findings to natural systems and to glucosinolate-containing foods is briefly discussed.Key Word Index-Lepidium sativum; Cruciferae; glucosinolate degradation.

From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water

Martins, Nayara Silva,ángel, Alix Y. Bastidas,Anghinoni, Jo?o M.,Lenard?o, Eder J.,Barcellos, Thiago,Alberto, Eduardo E.

supporting information, p. 87 - 93 (2021/11/03)

The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).

Radical trifunctionalization of hexenenitrile via remote cyano migration

Chang, Chenyang,Wu, Xinxin,Zhang, Huihui,Zhu, Chen

supporting information, p. 1005 - 1008 (2022/02/01)

A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alken

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

Liao, Xudong,Zhou, Yi,Ai, Chengmei,Ye, Cuijiao,Chen, Guanghui,Yan, Zhaohua,Lin, Sen

supporting information, (2021/11/01)

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.

Accelerated Discovery of α-Cyanodiarylethene Photoswitches

Hecht, Stefan,K?nig, Niklas F.,Mutruc, Dragos

supporting information, p. 9162 - 9168 (2021/07/01)

Cyanodiarylethene chromophores are able to undergo constitutional exchange via dynamic covalent chemistry (DCC). During this process, the central ethylene bridge of the molecular scaffold can be broken and thereby enables the assembly of a new combination of aryl moieties around the reformed ethylene bridge. The reversible CC double bond exchange has exemplarily been investigated using α-cyanostilbenes. Establishing a dynamic equilibrium reaction from α-cyanodiarylethene with arylacetonitriles under mild conditions has been the basis to access constitutional libraries of new photoswitches with potentially improved properties. When subject to irradiation with light of adequate wavelength, α-cyanodiarylethenes undergo Z/E isomerization followed by ring-closure. By screening the thus accessible dynamic chromophore libraries using a desired detection wavelength, we could identify specific dithienyl analogues that exhibit three-state photochromism. The combination of dynamic constitutional libraries of functional chromophores in combination with the light-guided screening and selection should lead to more rapid exploration of structural diversity dye chemistry.

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

Pirola, Margherita,Faverio, Chiara,Orlandi, Manuel,Benaglia, Maurizio

, p. 10247 - 10250 (2021/06/18)

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

Process route upstream and downstream products

Process route

1,6-diphenyl-3-aza-4-methylhex-3-ene-1,5-diyne
201489-34-1

1,6-diphenyl-3-aza-4-methylhex-3-ene-1,5-diyne

phenylacetonitrile
140-29-4

phenylacetonitrile

(Z)-1-cyano-1,2-diphenylpent-1-en-3-yne

(Z)-1-cyano-1,2-diphenylpent-1-en-3-yne

2-methyl-4,5-diphenylpyridine

2-methyl-4,5-diphenylpyridine

4-phenyl-3-butyne-2-one
1817-57-8

4-phenyl-3-butyne-2-one

Conditions
Conditions Yield
With tetrafluoroboric acid diethyl ether; 2-fluoropyridine; In tetrahydrofuran; di-isopropyl ether; at 97 ℃; for 0.516667h; Product distribution; Mechanism; other azadiyne;
3-cyano-2-hydroxy-3-phenyl-2-propyl-propionic acid
857480-72-9

3-cyano-2-hydroxy-3-phenyl-2-propyl-propionic acid

phenylacetonitrile
140-29-4

phenylacetonitrile

2-oxopentanoic acid
1821-02-9

2-oxopentanoic acid

Conditions
Conditions Yield
methyl 2-cyano-2-phenylacetate
30698-30-7

methyl 2-cyano-2-phenylacetate

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

phenylacetonitrile
140-29-4

phenylacetonitrile

2-methoxycarbonyl-2-phenylpropionitrile
79341-72-3

2-methoxycarbonyl-2-phenylpropionitrile

1-phenylethyl cyanide
1823-91-2

1-phenylethyl cyanide

Conditions
Conditions Yield
With potassium carbonate; In methanol; at 140 ℃; for 150h; Further Variations:; time; Product distribution; Kinetics;
13 % Chromat.
16 % Chromat.
54 % Chromat.
benzyl methoxymethyl ether
31600-55-2

benzyl methoxymethyl ether

(1-methoxymethoxy)ethylbenzene
94073-86-6

(1-methoxymethoxy)ethylbenzene

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

phenylacetonitrile
140-29-4

phenylacetonitrile

1-phenylethyl cyanide
1823-91-2

1-phenylethyl cyanide

Conditions
Conditions Yield
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate; at 135 - 140 ℃; for 0.075h; chemoselective reaction; Microwave irradiation; Neat (no solvent);
88%
19%
1-amino-2-phenylethanephosphonic acid
6324-00-1

1-amino-2-phenylethanephosphonic acid

2,4-diphenylcrotonaldehyde
5031-83-4

2,4-diphenylcrotonaldehyde

phenylacetaldehyde
122-78-1

phenylacetaldehyde

benzyl bromide
100-39-0

benzyl bromide

phenylacetonitrile
140-29-4

phenylacetonitrile

Conditions
Conditions Yield
In chloroform; at 25 ℃; for 0.5h; pH=4.79;
benzyl chloride
100-44-7

benzyl chloride

potassium ferrocyanide

potassium ferrocyanide

phenylacetonitrile
140-29-4

phenylacetonitrile

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With palladium diacetate; sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 10h; Inert atmosphere;
41 %Chromat.
8 %Chromat.
With copper(l) iodide; water; at 180 ℃; for 20h; Inert atmosphere; Sealed tube;
30 %Chromat.
3-cyano-2-hydroxy-2,3-diphenyl-propionic acid
408307-21-1

3-cyano-2-hydroxy-2,3-diphenyl-propionic acid

phenylacetonitrile
140-29-4

phenylacetonitrile

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
Conditions Yield
sodium cyanide
143-33-9,25596-52-5

sodium cyanide

benzyl chloride
100-44-7

benzyl chloride

phenylacetonitrile
140-29-4

phenylacetonitrile

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With -(1-MeO-4-CH2NMe3Cl-C6H2-(CH2)-2-yl-6)4; In water; at 60 ℃; for 12h;
8 % Chromat.
67 % Chromat.
potassium cyanide
151-50-8

potassium cyanide

benzyl chloride
100-44-7

benzyl chloride

phenylacetonitrile
140-29-4

phenylacetonitrile

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With Amberlyst A27; water; In toluene; at 100 ℃; for 85h;
1.5 % Chromat.
98 % Chromat.
potassium cyanide
151-50-8

potassium cyanide

benzyl bromide
100-39-0

benzyl bromide

dibenzyl ether
103-50-4

dibenzyl ether

phenylacetonitrile
140-29-4

phenylacetonitrile

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With aluminum oxide; In water; toluene; at 50 ℃; Product distribution; Irradiation; various amount of water and time;
55 % Chromat.
5.0 % Chromat.
5.8 % Chromat.

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