Welcome to LookChem.com Sign In|Join Free

Cas Database

104-85-8

104-85-8

Identification

  • Product Name:Benzonitrile,4-methyl-

  • CAS Number: 104-85-8

  • EINECS:203-244-8

  • Molecular Weight:117.15

  • Molecular Formula: C8H7N

  • HS Code:29269095

  • Mol File:104-85-8.mol

Synonyms:1-Cyano-4-methylbenzene;4-Cyanotoluene;4-Methylbenzonitrile;4-Methylcyanobenzene;4-Methylphenyl cyanide;4-Toluenitrile;4-Tolyl cyanide;NSC 70985;p-Cyanotoluene;p-Methylbenzonitrile;p-Toluenenitrile;p-Tolylcyanide;

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes: Xi:Irritant;

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • 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. Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

  • Fire-fighting measures: Suitable extinguishing media Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. This chemical is combustible. 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

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:p-?Tolunitrile
  • Packaging:100g
  • Price:$ 215
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TCI Chemical
  • Product Description:p-Tolunitrile >98.0%(GC)
  • Packaging:500g
  • Price:$ 321
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TCI Chemical
  • Product Description:p-Tolunitrile >98.0%(GC)
  • Packaging:25g
  • Price:$ 38
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TCI Chemical
  • Product Description:p-Tolunitrile >98.0%(GC)
  • Packaging:100g
  • Price:$ 100
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Methylbenzonitrile 97%
  • Packaging:250 g
  • Price:$ 176
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Methylbenzonitrile 97%
  • Packaging:50 g
  • Price:$ 104
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Methylbenzonitrile 97%
  • Packaging:1 kg
  • Price:$ 416
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:p-Tolunitrile 98%
  • Packaging:500g
  • Price:$ 205
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:p-Tolunitrile 98%
  • Packaging:25g
  • Price:$ 27
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:p-Tolunitrile 98%
  • Packaging:100g
  • Price:$ 60.2
  • Delivery:In stock
  • Buy Now

Relevant articles and documentsAll total 685 Articles be found

Photochemical equilibration/isomerization of p-, m-, and o-methylbenzonitrile

MacLeod, Paula J.,Pincock, Alexandra L.,Pincock, James A.,Thompson, Kim A.

, p. 6443 - 6450 (1998)

The phototransposition reactions in acetonitrile of p-, m-, and o-methylbenzonitrile have been studied. Any one of the three is converted to the other two by either a 1,2- or 1,3-isomerization in a primary photochemical step. However, the reactivities are quite different with the relative values for para:meta:ortho = 32:4:1. For both the para and meta isomers, extended irradiations approach a calculated steady-state composition of para:meta:ortho = 3:20:77. Quenching of the excited triplet state of the para and meta isomers with 2,4-dimethyl-1,3-butadiene indicates that these reactions are occurring from the excited singlet state. Irradiation of selectively labeled 2,6-dideuterio-4-methylbenzonitrile demonstrates that only the cyano-substituted carbon undergoes migration.

Reusable, highly active heterogeneous palladium catalyst by convenient self-encapsulation cross-linking polymerization for multiple carbon-carbon cross-coupling reactions at ppm to ppb palladium loadings

Donga, Zhongmin,Yea, Zhibin

, p. 3401 - 3414 (2014)

Designing reusable high-performance heterogeneous palladium (Pd) catalysts via convenient, economic synthesis is of great importance to the industrial applications of various carbon-carbon crosscoupling reactions. We demonstrate herein a convenient one-pot self-encapsulation synthesis of a heterogeneous Pd catalyst [Pd@PDEB, PDEB = poly(1,3-diethynylbenzene)] directly from commercially available, economic precursors. In the synthesis, the formation of the cross-linked polymer networks and Pd encapsulation are accomplished simultaneously, turning a homogeneous Pd polymerization catalyst into the heterogeneous cross-coupling catalyst. As a unique, practical heterogeneous catalyst, Pd@PDEB shows remarkably high activity, high reusability, and high versatility towards at least four types of cross-coupling reactions (Suzuki-Miyaura, Stille, allylic arylation, and Mizoroki-Heck reactions) with even difficult reactants (aryl chlorides and heteroaryl halides) under aerobic conditions with Pd loadings down to ppm or even ppb levels. Evidences from hot filtration and 3-phase tests demonstrate the heterogeneous nature of the catalyst with very low Pd leaching and negligible contributions of leached homogeneous Pd species towards the coupling reactions.

Isomerization of Methylbenzonitriles Catalysed by HZSM-5

Weigert, Frank J.

, p. 2653 - 2655 (1986)

The zeolite HZSM-5 catalyzes methyl migration in toluonitriles and dimethylbenzonitriles by intramolecular 1,2-shifts.Only the three dimethylbenzonitriles with 1,2,4-substituent pattern are small enough to take part in the shape selective reaction.

Dichlorobis(triphenylphosphine)nickel-catalyzed cross-coupling of aryl chlorides with intramolecularly stabilized group 13 metal alkylating reagents

Gelman,Schumann,Blum

, p. 7555 - 7558 (2000)

The intramolecularly stabilized alkyl and aryl aluminum complexes 1, 4 and 11, as well as the indium compounds 6, 9 and 10 cross-couple with a variety of chloroarenes at 8°C in the presence of NiCl2(PPh3)2 to give selectively the respective alkylated arenes in high yields. Addition of organic or inorganic bases lowers the reaction temperature to 50°C. (C) 2000 Elsevier Science Ltd.

Cul/1,10-phenanthroline: An efficient catalyst system for the cyanation of aryl halides

Zhu, Yi-Zhong,Cai, Chun

, p. 484 - 485 (2007)

Aryl nitriles have been prepared in good yields from the corresponding aryl halides with potassium hexacyanoferrate(II) using Cul/1,10-phenanthroline as the catalyst system. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and carbonyl substituents.

Cu-mediated nitrogen atom transfer via C≡N bond cleavage

Liu, Lixin,Dong, Jianyu,Zhang, Yaxing,Zhou, Yongbo,Yin, Shuang-Feng

, p. 9948 - 9952 (2015)

A nitrogen atom transfer to organic molecules via Cu-mediated C-N triple bond cleavage is firstly developed, which provides a variety of functionalized aryl nitriles from the readily accessible acetonitrile and aryl aldehydes.

Simple and efficient one-pot synthesis of nitriles from amides and oximes using in situ-generated burgess-type reagent

Rappai, John P.,Karthikeyan, Jayakumar,Prathapan, Sreedharan,Unnikrishnan, Perupparampil A.

, p. 2601 - 2606 (2011)

The dehydration of aldoximes and amides, and oxidation of benzoin are accomplished in one-pot using in situ-generated Burgess-type reagent. Taylor & Francis Group, LLC.

A versatile method for the conversion of aldoximes to nitriles using silica gel/thionyl chloride

Kazemi, Foad,Kiasat, Ali Reza,Fadavipoor, Elham

, p. 433 - 436 (2004)

A simple convenient procedure for dehydration of aldoximes has been developed using silica gel/thionyl chloride in heterogeneous conditions. The method has been found to be effective for a wide range of aromatic oximes.

-

Friedman,Shechter

, p. 2522 (1961)

-

Activation energies for the singlet excited state processes of substituted benzenes: Para, meta, and ortho isomers of methylbenzonitrile and methylanisole in acetonitrile

Gonzalez, Carlos M.,Pincock, James A.

, p. 8870 - 8871 (2004)

The rate constants of decay of the excited singlet states of the methylbenzonitriles (1-3) and the methylanisoles (4-6) have been determined by the measurement of fluorescence lifetimes over a broad range of temperatures (-45 to +65 °C) in acetonitrile. By fitting this data to a nonlinear expression that includes the Arrhenius equation, rate constants for the activated process (reaction) and the unactivated ones (fluorescence and intersystem crossing) can be reliably obtained. Available literature data for benzene, toluene, and ortho-xylene were also analyzed. The results indicate that the excited singlet state of substituted benzenes is quite reactive and forms a prefulvene biradical intermediate efficiently (quantum yield = 0.69 for benzene itself) by an activated route. In contrast, the efficiency of isolable product formation is quite low because the dominant process for this intermediate is returned to starting material. These observations explain why Ermolaev's rule does not apply to benzene derivatives. Copyright

An efficient and convenient KF/Al2O3 mediated synthesis of nitriles from aldehydes

Movassagh, Barahman,Shokri, Salman

, p. 6923 - 6925 (2005)

KF/Al2O3 brings about a facile one-pot and economical conversion of various aryl and alkyl aldehydes into the corresponding nitriles in high yields by reaction with hydroxylamine hydrochloride.

Cobalt/nitrophenolate-catalyzed selective conversion of aldoximes into nitriles or amides

Jang, Wonseok,Kim, Se Eun,Yang, Cheol Mo,Yoon, Sungwoo,Park, Myunghwan,Lee, Junseong,Kim, Youngjo,Kim, Min

, p. 120 - 123 (2015)

A novel cobalt/nitrophenolate complex has been synthesized, characterized and studied for their catalytic activities. Conversion of aldoximes to nitriles can be performed via in situ conditions from cobalt(II) acetate and 2,4-dinitrophenol. The rearrangement of aldoximes to amides via cobalt(II) acetate and 2-nitro-1-naphthol has also been demonstrated. A complete reversal of transformation was accomplished by modifying the cobalt salt and careful choice of both the nitrophenol ligand and reaction conditions.

Copper-Catalyzed Oxidation of Amines with Molecular Oxygen

Maeda, Yasunari,Nishimura, Takahiro,Uemura, Sakae

, p. 2399 - 2403 (2003)

An improved system for selective aerobic oxidation of amines to imines or nitriles is presented. It involves commercially available and inexpensive copper(I) or (II) chloride as catalyst, toluene as solvent, and MS3A as dehydrating agent under an atmospheric pressure of oxygen. A variety of amines can be used as substrates for this oxidation system to give the corresponding nitriles from primary amines (up to 97% yield; TON, up to 60) and the imines from secondary amines (up to 90% yield; TON, up to 45).

Dynamics of bond breaking in ion radicals. Mechanisms and reactivity in the reductive cleavage of carbon-fluorine bonds of fluoromethylarenes

Andrieux, Claude P.,Combellas, Catherine,Kanoufi, Fredéric,Savéant, Jean-Michel,Thiébault, André

, p. 9527 - 9540 (1997)

The reductive cleavage mechanism and reactivity of the carbon-fluorine bonds in fluoromethylarenes are investigated, in liquid ammonia and in DMF, by means of cyclic voltammetry and/or redox catalysis as a function of the number of fluorine atoms and of the structure of the aryl moiety. The reduction of the trifluoro compounds, eventually leading to complete defluorination, involves the di- and monofluoro derivatives as intermediates. Carbenes do not transpire along the reaction pathway. Application of the intramolecular dissociative electron transfer model allows the quantitative rationalization, in terms of driving force and intrinsic barrier, of the variation of the cleavage reactivity of the primary anion radical with the number of fluorine atoms and of the structure of the aryl moiety as well as with the solvating properties of the medium. When, related to the structural factors thus uncovered, the primary anion radical generates the di- and monofluoro intermediates far from the electrode surface, their reduction occurs homogeneously giving rise to an apparently direct six-electron process according to an internal redox catalysis mechanism. Conversely, with rapid cleavages, the reduction of the di- and monofluoro intermediates takes place at the electrode surface and the stepwise expulsion of the fluorides ions transpire in the cyclic voltammetric patterns.

COUPLING REACTION OF ORGANOMERCURY COMPOUNDS WITH ARYL HALIDES CATALYZED BY PALLADIUM COMPLEXES

Bumagin, N. A.,Kalinovskii, I. O.,Beletskaya, I. P.

, p. 1469 - 1473 (1983)

-

-

Coleman et al.

, p. 738 (1970)

-

A general and convenient catalytic synthesis of nitriles from amides and silanes

Zhou, Shaolin,Junge, Kathrin,Addis, Daniele,Das, Shoubhik,Beller, Matthias

, p. 2461 - 2464 (2009)

A new and convenient protocol for the catalytic dehydration of aromatic and aliphatic amides using silanes in the presence of catalytic amounts of fluoride is presented. The synthesis of aliphatic and aromatic nitriles proceeds with high selectivity under mild conditions. Notably, a wide substrate range is converted in good to excellent yields.

Palladium-catalyzed cyanation of aryl halides with CuSCN

Zhang, Guo-Ying,Yu, Jin-Tao,Hu, Mao-Lin,Cheng, Jiang

, p. 2710 - 2714 (2013)

A palladium-catalyzed cyanation of aryl halides and borons has been developed by employing cuprous thiocyanate as a safe cyanide source. This protocol avoids the use of a highly toxic cyanide source, providing aromatic nitriles in moderate to good yields with good functional tolerance.

Potassium, fluoride doped on alumina: An efficient catalyst for conversion of aldoximes into nitriles

Movassagh, Barahman,Shokri, Salman

, p. 887 - 890 (2005)

Potassium fluoride loaded on alumina catalyzed the dehydration of alkyl and aryl aldoximes into nitriles in good to high yields.

2-pyridyl cyanate: A useful reagent for the preparation of nitriles

Koo, Ja Seo,Lee, Jae In

, p. 3709 - 3713 (1996)

-

Nitrosation of Cyanamide: Preparation and Properties of the Elusive E- and Z-N'-Cyanodiazohydroxides

Guethner, Thomas,Huber, Evi,Sans, Juergen,Thalhammer, Franz

, (2020)

Nitrosation of cyanamide leads to unstable E/Z-cyanodiazohydroxides that easily deprotonate to E/Z-cyanodiazotates. Pursuing observations of E. Drechsel 145 years ago, the structure and reactivity of those products was determined, mainly in aqueous solution. Depending on the pH, three different thermal decomposition pathways give either N2O + HCN or N2 + HNCO. They were evaluated experimentally and by quantum mechanical calculations.

One-step synthesis of tolunitriles by heterogeneously catalyzed liquid-phase ammoxidation

Liu, Yuan,Zhong, Min,Yu, Wei,Ma, Yu-Long

, p. 2951 - 2954 (2005)

Tolunitriles have been efficiently synthesized by selective ammoxidation of corresponding xylene over silica-supported Co-Mn-Mg-Ni catalysts, without solvent for the first time in a one-pot procedure. The selectivity for mono-nitriles is almost 100%. Copyright Taylor & Francis, Inc.

The palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates

Chen, Jianbin,Sun, Yang,Liu, Bin,Liu, Dongfang,Cheng, Jiang

, p. 449 - 451 (2012)

A palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates has been developed, providing aryl nitriles in moderate to excellent yields. It represents a facile procedure to access aryl nitriles.

Aerobic oxidative dehydrogenation of benzyl alcohols to benzaldehydes by using a cyclometalated ruthenium catalyst

Taketoshi, Ayako,Beh, Xin Ning,Kuwabara, Junpei,Koizumi, Take-Aki,Kanbara, Takaki

, p. 3573 - 3576 (2012)

The ruthenium(III) complex bearing phenylpyridine as a cyclometalated ligand serves as an efficient catalyst for the aerobic oxidative dehydrogenation of benzyl alcohols to the corresponding benzaldehydes under mild conditions and for the one-pot synthesis of benzonitriles from benzyl alcohols with ammonia.

Stable palladium nanoparticles catalyzed synthesis of benzonitriles using K4[Fe(CN)6]

Ganapathy, Dhandapani,Kotha, Surya Srinivas,Sekar, Govindasamy

, p. 175 - 178 (2015)

A stable palladium nanocatalyst is used in the synthesis of benzonitriles by cyanation of aryl iodides. A nontoxic and economic potassium hexacyanoferrate was used as a safe cyanide source. A variety of benzonitriles are efficiently synthesized using the stable nanocatalyst. The catalyst was quantitatively recovered and reused without any apparent loss in the catalytic activity.

Rapid method of converting primary amides to nitriles and nitriles to primary amides by ZnCl2 using microwaves under different reaction conditions

Manjula, Krishnappa,Pasha, Mohamed Afzal

, p. 1545 - 1550 (2007)

A rapid and facile method for the conversion of primary amides to nitriles using inexpensive and readily available ZnCl2 in aqueous acetonitrile and their regeneration using ZnCl2-H2O-THF in the presence of acetamide under microwave irradiation in good yields is reported. The reactions go to completion within a minute. Copyright Taylor & Francis Group, LLC.

Phosphinoferrocene ureas: Synthesis, structural characterization, and catalytic use in palladium-catalyzed cyanation of aryl bromides

?koch, Karel,Císa?ová, Ivana,?těpni?ka, Petr

, p. 1942 - 1956 (2015)

Phosphinoferrocene ureas Ph2PfcCH2NHCONR2, where NR2 = NH2 (1a), NHMe (1b), NMe2 (1c), NHCy (1d), and NHPh (1e); the analogous thiourea Ph2PfcCH2NHCSNHPh (1f); and the acetamido derivative Ph2PfcCH2NHCOMe (1g) (Cy = cyclohexyl, fc = ferrocene-1,1′-diyl) were prepared via three different approaches starting from Ph2PfcCH2NH2·HCl (3·HCl) or Ph2PfcCHO (4). The reactions of the representative ligand 1e with [PdCl2(cod)] (cod = cycloocta-1,5-diene) afforded [PdCl(μ-Cl)(1e-κP)2]2 or [PdCl2(1e-κP)2]2 depending on the metal-to-ligand stoichiometry, whereas those with [PdCl(η3-C3H5)]2 and [PdCl(LNC)]2 produced the respective bridge cleavage products, [PdCl(η3-C3H5)(1e-κP)] and [PdCl(LNC)(1e-κP)] (LNC = [(2-dimethylamino-κN)methyl]phenyl-κC1). Attempts to involve the polar pendant in coordination to the Pd(II) center were unsuccessful, indicating that the phosphinoferrocene ureas 1 bind Pd(II) preferentially as modified phosphines rather than bifunctional donors. When combined with palladium(II) acetate, the ligands give rise to active catalysts for Pd-catalyzed cyanation of aryl bromides with potassium hexacyanoferrate(II). Optimization experiments revealed that the best results are obtained in 50% aqueous dioxane with a catalyst generated from 1 mol % of palladium(II) acetate and 2 mol % of 1e in the presence of 1 equiv of Na2CO3 as the base and half molar equivalent of K4[Fe(CN)6]·3H2O. Under such optimized conditions, bromobenzenes bearing electron-donating substituents are cyanated cleanly and rapidly, affording the nitriles in very good to excellent yields. In the case of substrates bearing electron-withdrawing groups, however, the cyanation is complicated by the hydrolysis of the formed nitriles to the respective amides, which reduces the yield of the desired primary product. Amine- and nitro-substituted substrates are cyanated only to a negligible extent, the former due to their metal-scavenging ability.

Novel trans-spanned palladium complexes as efficient catalysts in mild and amine-free cyanation of aryl bromides under air

Grossman, Olga,Gelman, Dmitri

, p. 1189 - 1191 (2006)

The use of a novel trans-spanned palladium complex as an efficient and selective catalyst in the cyanation of aryl halides is described. The suggested reaction conditions are mild, exhibit good scope of substrates, and circumvent the need for an inert atmosphere and amine co-ligands.

One-step conversion of aldehydes into nitriles in dry media under microwave irradiation

Feng, Jun-Cai,Liu, Bin,Dai, Li,Bian, Ning-Sheng

, p. 3765 - 3768 (1998)

Aldehydes undergo rapid reaction with hydroxylammonium chloride using HCOOH/SiO2 as solid support catalyst, under microwave irradiation without solvent to affords nitriles in 60-90% yields.

A highly efficient and reusable palladium(II)/cationic 2,2′-bipyridyl-catalyzed stille coupling in water

Wu, Wei-Yi,Liu, Ling-Jun,Chang, Fen-Ping,Cheng, Yu-Lun,Tsai, Fu-Yu

, (2016)

A water-soluble PdCl2 (NH3 )2 /cationic 2,2′ -bipyridyl system was found to be a highly efficient catalyst for Stille coupling of aryl iodides and bromides with organostannanes. The coupling reaction was conducted at 110°C in water, under aerobic conditions, in the presence of NaHCO3 as a base to afford corresponding Stille coupling products in good to high yields. When aryltributylstannanes were employed, the reactions proceeded smoothly under a very low catalyst loading (as little as 0.0001 mol %). After simple extraction, the residual aqueous phase could be reused in subsequent runs, making this Stille coupling economical. In the case of tetramethylstannane, however, a greater catalyst loading (1 mol %) and the use of tetraethylammonium iodide as a phase-transfer agent were required in order to obtain satisfactory yields.

Synthesis of aryl dihydrothiazol acyl shikonin ester derivatives as anticancer agents through microtubule stabilization

Lin, Hong-Yan,Li, Zi-Kang,Bai, Li-Fei,Baloch, Shahla Karim,Wang, Fang,Qiu, Han-Yue,Wang, Xue,Qi, Jin-Liang,Yang, Raong-Wu,Wang, Xiao-Ming,Yang, Yong-Hua

, p. 93 - 106 (2015)

The high incidence of cancer and the side effects of traditional anticancer drugs motivate the search for new and more effective anticancer drugs. In this study, we synthesized 17 kinds of aryl dihydrothiazol acyl shikonin ester derivatives and evaluated their anticancer activity through MTT assay. Among them, C13 showed better antiproliferation activity with IC50 = 3.14 ± 0.21 μM against HeLa cells than shikonin (IC50 = 5.75 ± 0.47 μM). We then performed PI staining assay, cell cycle distribution, and cell apoptosis analysis for C13 and found that it can cause cell arrest in G2/M phase, which leads to cell apoptosis. This derivative can also reduce the adhesive ability of HeLa cells. Docking simulation and confocal microscopy assay results further indicated that C13 could bind well to the tubulin at paclitaxel binding site, leading to tubulin polymerization and mitotic disruption.

Pd/C: A recyclable catalyst for cyanation of aryl bromides

Zhu, Yi-Zhong,Cai, Chun

, p. 2401 - 2404 (2007)

Aryl cyanides have been prepared from the corresponding aryl bromides with potassium hexacyanoferrate(II) using Pd/C as a catalyst. It is shown that the addition of Bu3N is the key factor in obtaining the corresponding aryl cyanides. Furthermore, the catalyst can be recycled by filtration and washing sequences, making the method also attractive for industrial applications. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Pd/C-catalyzed cyanation of aryl halides in aqueous PEG

Chen, Gong,Weng, Jiang,Zheng, Zhanchao,Zhu, Xinhai,Cai, Yaoyao,Cai, Jiwen,Wan, Yiqian

, p. 3524 - 3528 (2008)

An environmentally friendly Pd/C-PEG-H2O system was developed for the cyanation of aryl halides under microwave irradiation. A wide range of aryl bromides, iodides, and some activated chlorides were demonstrated to be cyanated smoothly by using nontoxic K4[Fe(CN)6] ·3H2O as the cyanide source. There is no phosphorus- or nitrogen-containing ligand or solvent involved. Moreover, this reaction can be carried out without the protection of inert atmosphere. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Reduction of Benzylic Halides with Diethylzinc Using Tetrakis(triphenylphosphine)palladium as Catalyst

Agrios, Konstantinos A.,Srebnik, Morris

, p. 6908 - 6910 (1993)

-

Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets

Hua, Manli,Song, Jinliang,Huang, Xin,Liu, Huizhen,Fan, Honglei,Wang, Weitao,He, Zhenhong,Liu, Zhaotie,Han, Buxing

, p. 21479 - 21485 (2021)

Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.

A new modified electrophilic cyanation of aromatics with activated aryl cyanates

Buttke,Reiher,Niclas

, p. 2237 - 2243 (1992)

The selective cyanation of electron-rich aromatics succeeds in moderate to good yields with the activated aryl cyanates 1a-d using AlCl3/HCl. The formation of p-isomeres is preferred.

Cyanation of aryl chlorides using a microwave-assisted, copper-catalyzed concurrent tandem catalysis methodology

Coughlin, Mary M.,Kelly, Colin K.,Lin, Shirley,Macarthur, Amy H. Roy

, p. 3537 - 3543 (2013)

A microwave-assisted, copper-catalyzed concurrent tandem catalytic (CTC) methodology has been developed for the cyanation of aryl chlorides, where the aryl chloride is first converted to an aryl iodide via halogen exchange and the aryl iodide is subsequently transformed to the aryl nitrile. A variety of aryl chlorides were converted to aryl nitriles in 44-97% yield using 20 mol % of CuI, 40 mol % of N,N'-cyclohexane-1,2-diamine, and 1.2 equiv of KCN in acetonitrile at 200 C after 1-2 h. The same copper/ligand system served as a multifunctional catalyst for both steps of the concurrent catalytic process. Unlike our previously reported CTC hydrodehalogenation of aryl chlorides, CTC cyanation was catalytic in iodide. Kinetic simulations of the proposed CTC mechanism were consistent with experimental results and stipulate the relative reaction rates of the two catalytic cycles necessary to achieve reasonable yields of product. This article not subject to U.S. Copyright. Published 2013 by the American Chemical Society.

Para-Selective Cyanation of Arenes by H-Bonded Template

Pimparkar, Sandeep,Bhattacharya, Trisha,Maji, Arun,Saha, Argha,Jayarajan, Ramasamy,Dutta, Uttam,Lu, Gang,Lupton, David W.,Maiti, Debabrata

, p. 11558 - 11564 (2020)

The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work, we demonstrate the para-selective introduction of versatile nitrile moiety, enabled by a detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools, which heralds the inception of para-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.

Deciphering a 20-Year-Old Conundrum: The Mechanisms of Reduction by the Water/Amine/SmI2 Mixture

Maity, Sandeepan,Hoz, Shmaryahu

, p. 18394 - 18400 (2015)

The reaction of SmI2 with the substrates 3-methyl-2-butanone, benzyl chloride, p-cyanobenzyl chloride, and anthracene were studied in the presence of water and an amine. In all cases, the water content versus rate profile shows a maximum at around 0.2 M H2O. The rate versus amine content profile shows in all cases, except for benzyl chloride, saturation behavior, which is typical of a change in the identity of the rate-determining step. The mechanism that is in agreement with the observed data is that electron transfer occurs in the first step. With substrates that are not very electrophilic, the intermediate radical anions lose the added electron back to samarium(III) relatively quickly and the reaction cannot progress efficiently. However, in a mixture of water/amine, the amine deprotonates a molecule of water coordinated to samarium(III). The negatively charged hydroxide, which is coordinated to samarium(III), reduces its electrophilicity, and therefore, lowers the rate of back electron transfer, which allows the reaction to progress. In the case of benzyl chloride, in which electron transfer is rate determining, deprotonation by the amine is coupled to the electron-transfer step.

Multicomponent Pyrazole Synthesis from Alkynes, Nitriles, and Titanium Imido Complexes via Oxidatively Induced N-N Bond Coupling

Pearce, Adam J.,Harkins, Robin P.,Reiner, Benjamin R.,Wotal, Alexander C.,Dunscomb, Rachel J.,Tonks, Ian A.

, p. 4390 - 4399 (2020)

Pyrazoles are an important class of heterocycles found in a wide range of bioactive compounds and pharmaceuticals. Pyrazole synthesis often requires hydrazine or related reagents where an intact N-N bond is conservatively installed into a pyrazole precursor fragment. Herein, we report the multicomponent oxidative coupling of alkynes, nitriles, and Ti imido complexes for the synthesis of multisubstituted pyrazoles. This modular method avoids potentially hazardous reagents like hydrazine, instead forming the N-N bond in the final step via oxidation-induced coupling on Ti. The mechanism of this transformation has been studied in-depth through stoichiometric reactions of the key diazatitanacyclohexadiene intermediate, which can be accessed via multicomponent coupling of Ti imidos with nitriles and alkynes, ring opening of 2-imino-2H-azirines, or direct metalation of 4-azadiene-1-amine derivatives. The critical transformation in this reaction is the 2-electron oxidation-induced N-N coupling on Ti. This is a rare example of formal N-N coupling on a metal center, which likely occurs through an electrocyclic mechanism analogous to a Nazarov cyclization. Conveniently, these 2-electron-oxidized diazatitanacyclohexadiene intermediates can be accessed via disproportionation of the 1-electron-oxidized species, which allows utilization of weak oxidants such as TEMPO

Naphthochromenones: Organic Bimodal Photocatalysts Engaging in Both Oxidative and Reductive Quenching Processes

Mateos, Javier,Rigodanza, Francesco,Vega-Pe?aloza, Alberto,Sartorel, Andrea,Natali, Mirco,Bortolato, Tommaso,Pelosi, Giorgio,Companyó, Xavier,Bonchio, Marcella,Dell'Amico, Luca

, p. 1302 - 1312 (2020)

Twelve naphthochromenone photocatalysts (PCs) were synthesized on gram scale. They absorb across the UV/Vis range and feature an extremely wide redox window (up to 3.22 eV) that is accessible using simple visible light irradiation sources (CFL or LED). Their excited-state redox potentials, PC*/PC.? (up to 1.65 V) and PC.+/PC* (up to ?1.77 V vs. SCE), are such that these novel PCs can engage in both oxidative and reductive quenching mechanisms with strong thermodynamic requirements. The potential of these bimodal PCs was benchmarked in synthetically relevant photocatalytic processes with extreme thermodynamic requirements. Their ability to efficiently catalyze mechanistically opposite oxidative/reductive photoreactions is a unique feature of these organic photocatalysts, thus representing a decisive advance towards generality, sustainability, and cost efficiency in photocatalysis.

Green synthesis of palladium nanocatalyst derived from the β-cyclodextrin used as effective heterogeneous catalyst for cyanation of aryl halides

Baran, Talat,Nasrollahzadeh, Mahmoud

, (2020)

In this study, preparation of highly stable palladium nanoparticles (Pd NPs) on Schiff base modified β-cyclodextrin (β-CD-Sch) in the absence of reducing agents has been successfully carried out. Pd NPs&at;β-CD-Sch has then been applied as nanocatalyst in the synthesis of benzonitriles via cyanation reaction using K4Fe(CN)6, which is a low cost, commercially available and non-toxic cyanide source. A series of benzonitriles containing different substrates were successfully fabricated with 77–98percent yields using Pd NPs&at;β-CD-Sch. Moreover, Pd NPs&at;β-CD-Sch catalyst was quantitatively recovered and reutilized several times, showing good reaction yields. This work revealed that i) prepared β-CD-Sch is an effective stabilizer for the fabrication of Pd NPs and ii) Pd NPs&at;β-CD-Sch catalyst play an important role in the fabrication of benzonitriles.

Cu2O-mediated room temperature cyanation of aryl boronic acids/esters and TMSCN

Ye, Yong,Wang, Yanhua,Liu, Pengtang,Han, Fushe

, p. 27 - 30 (2013)

A method for the efficient and reliable synthesis of aryl nitriles via the Cu2O-catalyed cross-coupling of aryl boronic acids or esters and TMSCN is presented. A broad range of substrates decorated by electron-rich and deficient, sterically very congested, and labile functionalities were tolerated. Moreover, the reaction can proceed under mild conditions at room temperature. These advantages paired with the use of cheap, readily available, and halogen-free Cu2O as catalysts make the protocol an appealing option for aryl cyanations. A method for the efficient and reliable synthesis of aryl nitriles via the Cu2O-catalyed cross-coupling of aryl boronic acids or esters and TMSCN is presented. The room temperature operation paired with the use of cheap, readily available, and halogen-free Cu2O as catalysts makes the protocol an appealing option for aryl cyanations. Copyright

Direct, facile synthesis of acyl azides and nitriles from carboxylic acids using bis(2-methoxyethyl)aminosulfur trifluoride

Kangani, Cyrous O.,Day, Billy W.,Kelley, David E.

, p. 5933 - 5937 (2007)

A mild, efficient, and practical method for the one-step synthesis of acyl azides from carboxylic acids using bis(2-methoxyethyl)aminosulfur trifluoride is described. The reaction was easily extended to the synthesis of the corresponding nitriles by the inclusion of phosphorous reagents. The method can be applied to the synthesis of optically active nitriles in high yields, and is compatible with fluorous phosphines.

Cu(NO3)2·3H2O-mediated cyanation of aryl iodides and bromides using DMF as a single surrogate of cyanide

Zhang, Lianpeng,Lu, Ping,Wang, Yanguang

, p. 2840 - 2843 (2015)

Aryl nitriles were prepared through Cu(NO3)2·3H2O-mediated cyanation of aryl iodides and bromides using DMF as a single surrogate of cyanide. Moreover, this protocol could be scalable and practiced with benign operation.

-

Hodgson,Heyworth

, p. 1131 (1949)

-

Pyrolysis and Photolysis of 1-Aroylamino-4,5-diaryl-1,2,3-triazoles: Generation and Thermal Transformations of 4,5-Diaryl-1,2,3-triazolyl Radicals

Hadjiantoniou-Maroulis,Charalambopoulos,Maroulis

, p. 891 - 894 (1998)

The pyrolysis of 1-aroylamino-4,5-diphenyl-1,2,3-triazoles 1 yields, pressumably via the 4,5-diphenyl-1,2,3-triazolyl radical (2a), 2,3-diphenyl-2H-azirine (11a) and 2-aryl-4,5-diphenylimidazoles 14 as the major products. Upon irradiation 1-benzoylamino-4,5-diphenyl-1,2,3-triazole (1a) gives 4,5-diphenyl-1(2)H-1,2,3-triazole (4a) via the 1,2,3-triazolyI radical 2a, together with benzamide (5a) and 1,2-bisbenzoylhydrazine (6a). Products 5a and 6a result from the benzoylamino radical 3a by hydrogen atom abstraction and dimerization respectively.

Thermodynamics, kinetics, and dynamics of the two alternative aniomesolytic fragmentations of C-O bonds: An electrochemical and theoretical study

Pisano, Luisa,Farriol, Maria,Asensio, Xavier,Gallardo, Iluminada,Gonzalez-Lafont, Angels,Lluch, Jose M.,Marquet, Jordi

, p. 4708 - 4715 (2002)

Fragmentation reactions of radical anions (mesolytic cleavages) of cyanobenzyl alkyl ethers (intramolecular dissociative electron transfer, heterolytic cleavages) have been studied electrochemically. The intrinsic barriers for the processes have been esta

Iodine-catalyzed, efficient, one-pot protocol for the conversion of araldehydes into 5-aryl-1H-tetrazoles

Reddy, M.B.Madhusudana,Pasha

, p. 2081 - 2085 (2011)

An easy access to various 5-aryl-1H-tetrazoles by a one-pot direct conversion of aldehydes to tetrazoles without the isolation of the intermediate nitriles using commercially available iodine as a catalyst is described. The protocol offers advantages in terms of good yields, mild reaction conditions, short reaction times, and use of readily available environmentally compatible catalyst. Copyright

Cyanide abstractions from benzyl isocyanides by Tri-n-Butyltin radical: An implication of imbalanced transition state and entropy control of reactivities

Kim, Sung Soo,Kim, Hoon,Yang, Ki Woong

, p. 5303 - 5306 (1997)

The relative rates and Hammett constants (ρ = 0.70) are immune from the temperature effects thus violating reactivity/selectivity principle. The polar TS can be classified as the 'imbalanced TS'. The substituents control the extent of the bond fissions end the rates are governed by the entropy term.

Aldoxime- and hydroxy-functionalized chalcones as highly potent and selective monoamine oxidase-B inhibitors

Oh, Jong Min,Rangarajan,Chaudhary, Reeta,Gambacorta, Nicola,Nicolotti, Orazio,Kumar, Sunil,Mathew, Bijo,Kim, Hoon

, (2021/11/16)

A panel of 30 chalcone derivatives, including 19 aldoxime-chalcone ethers (ACE), and 11 hydroxyl?chalcones (HC), previously synthesized using a Pd-catalyzed C–O cross-coupling method were evaluated for their inhibitory activities against monoamine oxidases (MAOs), cholinesterases (ChEs), and β-secretase (BACE-1). HC6 was the most potent inhibitor of MAO-B with an IC50 value of 0.0046 μM and a selectivity index (SI) of 1,113. HC3 also potently inhibited MAO-B (IC50 = 0.0067 μM) and had the highest SI (1,455). ACE7 and ACE15 were also potent MAO-B inhibitors (IC50 = 0.012 and 0.018 μM, respectively), with SIs of 260 and 1,161, respectively. HC3 and HC6 were reversible competitive inhibitors of MAO-B, with Ki values of 0.0036 and 0.0013 μM, respectively. A structure–activity relationship revealed that methyl and fluorine substituents contributed to increasing both inhibition and selectivity. ACE7 was the most effective inhibitor of MAO-A (IC50 = 1.49 μM), followed by ACE3 (IC50 = 3.75 μM). No compounds effectively inhibited AChE, BChE, or BACE-1. A docking simulation showed that the ligand efficiency and docking scores of HC3 and HC6 toward MAO-B were consistent with the experimental IC50 values. These results suggest that HC3 and HC6 can be considered promising candidates for the treatment of neurological disorders.

Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources

Doyle, Abigail G.,Gandhi, Shivaani S.,Jiang, Shutian,Kariofillis, Stavros K.,Martinez Alvarado, Jesus I.,?urański, Andrzej M.

supporting information, p. 1045 - 1055 (2022/01/19)

Ni/photoredox catalysis has emerged as a powerful platform for C(sp2)–C(sp3) bond formation. While many of these methods typically employ aryl bromides as the C(sp2) coupling partner, a variety of aliphatic radical sources have been investigated. In principle, these reactions enable access to the same product scaffolds, but it can be hard to discern which method to employ because nonstandardized sets of aryl bromides are used in scope evaluation. Herein, we report a Ni/photoredox-catalyzed (deutero)methylation and alkylation of aryl halides where benzaldehyde di(alkyl) acetals serve as alcohol-derived radical sources. Reaction development, mechanistic studies, and late-stage derivatization of a biologically relevant aryl chloride, fenofibrate, are presented. Then, we describe the integration of data science techniques, including DFT featurization, dimensionality reduction, and hierarchical clustering, to delineate a diverse and succinct collection of aryl bromides that is representative of the chemical space of the substrate class. By superimposing scope examples from published Ni/photoredox methods on this same chemical space, we identify areas of sparse coverage and high versus low average yields, enabling comparisons between prior art and this new method. Additionally, we demonstrate that the systematically selected scope of aryl bromides can be used to quantify population-wide reactivity trends and reveal sources of possible functional group incompatibility with supervised machine learning.

Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones

Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki

supporting information, p. 3799 - 3802 (2022/04/07)

The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.

Construction of N-Acyliminophosphoranes via Iron(II)-Catalyzed Imidization of Phosphines with N-Acyloxyamides

Lin, Sen,Lin, Bo,Zhang, Zongtao,Chen, Jianhui,Luo, Yanshu,Xia, Yuanzhi

, p. 3302 - 3306 (2022/05/05)

Employing FeCl2as a cheap and readily available catalyst, a facile imidization of phosphines with N-acyloxyamides is described, affording synthetically useful N-acyliminophosphoranes with high functional group tolerance. The transformation is easily performed under an air atmosphere at room temperature and could be scaled up to gram scale with a catalyst loading of 1 mol %. The iminophosphoranyl moiety in the product was further utilized as an effective directing group for controllable ortho C(sp2)-H bond amidations under Rh(III) catalysis.

Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation

Hui, Yu,Luo, Qingsong,Qin, Yucai,Song, Lijuan,Wang, Hai,Wang, Liang,Xiao, Feng-Shou

, p. 2164 - 2172 (2021/09/20)

The performances of heterogeneous catalysts can be effectively tuned by changing the catalyst structures. Here we report a controllable nitrile synthesis from alcohol ammoxidation, where the nitrile hydration side reaction could be efficiently prevented by changing the manganese oxide catalysts. α-Mn2O3 based catalysts are highly selective for nitrile synthesis, but MnO2-based catalysts including α, β, γ, and δ phases favour the amide production from tandem ammoxidation and hydration steps. Multiple structural, kinetic, and spectroscopic investigations reveal that water decomposition is hindered on α-Mn2O3, thus to switch off the nitrile hydration. In addition, the selectivity-control feature of manganese oxide catalysts is mainly related to their crystalline nature rather than oxide morphology, although the morphological issue is usually regarded as a crucial factor in many reactions.

Process route upstream and downstream products

Process route

2-phenyl-3-<i>p</i>-tolyl-oxirane
22440-35-3

2-phenyl-3-p-tolyl-oxirane

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

benzaldehyde
100-52-7

benzaldehyde

benzonitrile
100-47-0

benzonitrile

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
With sodium azide; copper(II) choride dihydrate; oxygen; In N,N-dimethyl-formamide; at 100 ℃; for 10h; Schlenk technique; Sealed tube;
31 %Chromat.
25 %Chromat.
22 %Chromat.
21 %Chromat.
4-methyl benzaldehyde benzoylhydrazone
7253-65-8

4-methyl benzaldehyde benzoylhydrazone

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

benzaldehyde
100-52-7

benzaldehyde

benzonitrile
100-47-0

benzonitrile

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
With copper; at 220 - 320 ℃; for 0.666667h; Product distribution;
29%
28%
5%
3%
para-methylbenzamide
619-55-6

para-methylbenzamide

4-methylthiobenzamide
2362-62-1

4-methylthiobenzamide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
With triethylamine; trichlorophosphate; In water; at 70 - 75 ℃; for 0.0833333h; microwave irradiation;
2,2,4,5-Tetra-p-tolyl-2,5-dihydro-oxazole
112120-94-2

2,2,4,5-Tetra-p-tolyl-2,5-dihydro-oxazole

bis(p-methylphenyl)-methanone
611-97-2

bis(p-methylphenyl)-methanone

C<sub>31</sub>H<sub>29</sub>NO
134836-33-2

C31H29NO

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
In benzene; for 6h; Irradiation;
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

dimethyl sulfoxide
67-68-5,8070-53-9

dimethyl sulfoxide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
In acetonitrile; at 20 ℃; for 4h;
88%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

para-chlorotoluene
106-43-4

para-chlorotoluene

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
Conditions Yield
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc; In acetonitrile; at 80 ℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube;
37%
4%
1%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

para-bromotoluene
106-38-7

para-bromotoluene

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
With potassium phosphate; C14H26N4; palladium diacetate; In N,N-dimethyl-formamide; at 110 ℃; for 18h;
75 %Spectr.
6 %Spectr.
para-bromotoluene
106-38-7

para-bromotoluene

P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
With tert.-butyl lithium; In tetrahydrofuran; hexane; at -78 ℃; Product distribution; different reagents and reaction temperature;
3-phenyl-1-(p-tolyl)-2,3-diazaprop-2-en-1-one
30410-39-0

3-phenyl-1-(p-tolyl)-2,3-diazaprop-2-en-1-one

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
at 750 ℃; for 0.75h; under 0.005 - 0.04 Torr; Mechanism;
4 % Spectr.
4 % Spectr.
2 % Spectr.
3,3-diphenyl-1-p-tolyl-2-azaprop-2-en-1-one
74143-80-9

3,3-diphenyl-1-p-tolyl-2-azaprop-2-en-1-one

benzophenone
119-61-9

benzophenone

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

benzonitrile
100-47-0

benzonitrile

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
Conditions Yield
at 900 ℃; for 0.75h; under 0.005 Torr; Mechanism;
71 % Spectr.
4 % Spectr.
3 % Spectr.
2 % Spectr.
2 % Spectr.
6 % Spectr.

Global suppliers and manufacturers

Global( 88) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • Simagchem Corporation
  • Business Type:Manufacturers
  • Contact Tel:+86-592-2680277
  • Emails:sale@simagchem.com
  • Main Products:110
  • Country:China (Mainland)
  • Chemwill Asia Co., Ltd.
  • Business Type:Manufacturers
  • Contact Tel:021-51086038
  • Emails:sales@chemwill.com
  • Main Products:30
  • Country:China (Mainland)
  • EAST CHEMSOURCES LIMITED
  • Business Type:Manufacturers
  • Contact Tel:86-532-81906761
  • Emails:josen@eastchem-cn.com
  • Main Products:97
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Career Henan Chemical Co
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-371-86658258
  • Emails:purchase@coreychem.com
  • Main Products:137
  • Country:China (Mainland)
  • Kono Chem Co.,Ltd
  • Business Type:Other
  • Contact Tel:86-29-86107037-8015
  • Emails:info@konochemical.com
  • Main Products:83
  • Country:China (Mainland)
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 104-85-8
Post Buying Request Now
close
Remarks: The blank with*must be completed