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102-93-2

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102-93-2 Usage

General Description

Benzenepropanamide, also known as N-phenylpropionamide or benzylpropanamide, is a chemical compound consisting of a benzene ring connected to a propanamide group. Benzenepropanamide may serve as a starting material or intermediate for the creation of more complex organic molecules, pharmaceuticals, or specialty chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 12, p. 76, 1947 DOI: 10.1021/jo01165a010

Check Digit Verification of cas no

The CAS Registry Mumber 102-93-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 2 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 102-93:
(5*1)+(4*0)+(3*2)+(2*9)+(1*3)=32
32 % 10 = 2
So 102-93-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H11NO/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H2,10,11)

102-93-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-phenylpropanamide

1.2 Other means of identification

Product number -
Other names Ph-CH2CH2-CO-NH2

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:102-93-2 SDS

102-93-2Relevant articles and documents

Supported Gold Nanoparticles-Catalyzed Microwave-Assisted Hydration of Nitriles to Amides under Base-Free Conditions

Kumar, Sandeep,Sharma, Saurabh,Das, Pralay

, p. 2889 - 2894 (2016)

Polystyrene-supported gold (Au@PS) nanoparticles were synthesized by the reduction deposition approach and well characterized by UV-visible, XRD, TEM, SAED, EDX, and XPS studies. The Au@PS was applied as catalyst for the hydration of nitriles to amides in water under microwave irradiation. Several functionalized aromatic, heterocyclic and aliphatic nitriles were found to be active for synthesis of the corresponding amides where no activation of water by base, ligand and support is needed. Easy recovery, negligible leaching and recyclability for up to eight runs are added advantages of the catalyst under water-mediated reaction conditions. (Figure presented.).

A selective hydration of nitriles catalysed by a Pd(OAc)2-based system in water

Sanz Sharley, Daniel D.,Williams, Jonathan M.J.

, p. 4090 - 4093 (2017)

In situ formation of a [Pd(OAc)2bipy] (bipy = 2,2′-bipyridyl) complex in water selectively catalyses the hydration of a wide range of organonitriles at 70 °C. Catalyst loadings of 5 mol% afford primary amide products in excellent yields in the absence of hydration-promoting additives such as oximes and hydroxylamines.

Efficient and selective hydration of nitriles to amides in aqueous systems with Ru(II)-phosphaurotropine catalysts

Bolyog-Nagy, Evelin,Udvardy, Antal,Joó, Ferenc,Kathó, ágnes

, p. 3615 - 3617 (2014)

A simple and efficient synthesis of amides by selective hydration of aromatic and aliphatic nitriles is described. The catalysts are prepared in situ from easily available Ru-precursors and ligands using water as the solvent. The most active catalyst, is obtained from [RuCl2(dmso)4] and benzylated 1,3,5-triaza-7-phosphaadamantane. Of the 16 substrates examined, 92-99% conversions of 14 nitriles were achieved in one hour at reflux temperature.

Highly Active Platinum Catalysts for Nitrile and Cyanohydrin Hydration: Catalyst Design and Ligand Screening via High-Throughput Techniques

Xing, Xiangyou,Xu, Chen,Chen, Bo,Li, Chengcheng,Virgil, Scott C.,Grubbs, Robert H.

, p. 17782 - 17789 (2018)

Nitrile hydration provides access to amides that are indispensable to researchers in chemical and pharmaceutical industries. Prohibiting the use of this venerable reaction, however, are (1) the dearth of biphasic catalysts that can effectively hydrate nitriles at ambient temperatures with high turnover numbers and (2) the unsolved challenge of hydrating cyanohydrins. Herein, we report the design of new "donor-acceptor"-type platinum catalysts by precisely arranging electron-rich and electron-deficient ligands trans to one other, thereby enhancing both the nucleophilicity of the hydroxyl group and the electrophilicity of the nitrile group. Leveraging a high-throughput, automated workflow and evaluating a library of bidentate ligands, we have discovered that commercially available, inexpensive DPPF [1,1′-ferrocenendiyl-bis(diphenylphosphine)] provides superior reactivity. The corresponding "donor-acceptor"-type catalyst 2a is readily prepared from (DPPF)PtCl2, PMe2OH, and AgOTf. The enhanced activity of 2a permits the hydration of a wide range of nitriles and cyanohydrins to proceed at 40 °C with excellent turnover numbers. Rational reevaluation of the ligand structure has led to the discovery of modified catalyst 2c, harboring the more electron-rich 1,1′-bis[bis(5-methyl-2-furanyl)phosphino] ferrocene ligand, which demonstrates the highest activity toward hydration of nitriles and cyanohydrins at room temperature. Finally, the correlation between the electron-donating ability of the phosphine ligands with catalyst efficiencies of 2a, 2c, 2d, and 2e in the hydration of nitrile 7 are examined, and the results support the "donor-acceptor" hypothesis.

A One-Flask Conversion of Carboxylic Acids into Nitriles

Imamoto, Tsuneo,Takaoka, Tomoko,Yokoyama, Masataka

, p. 142 - 143 (1983)

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Solid-supported ruthenium(0): An efficient heterogeneous catalyst for hydration of nitriles to amides under microwave irradiation

Kumar, Sandeep,Das, Pralay

, p. 2987 - 2990 (2013)

Solid-supported ruthenium(0) was synthesized by the reduction deposition method and used as a heterogeneous catalyst for the hydration of nitriles to amides under microwave irradiation. A wide range of aromatic, α,β-unsaturated and aliphatic nitriles were efficiently converted to their corresponding primary amides under milder conditions. The catalyst was found to be very stable under moisture and microwave irradiation, easily separable from the reaction mixture, to cause negligible metal contamination of the product and was recyclable up to ten times without significant loss of catalytic activity.

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Carmack,DeTar

, p. 2029,2032, 2755 (1946)

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Chemoselective transfer hydrogenation of α,β-unsaturated carbonyls using palladium immobilized ionic liquid catalyst

Patil, Nilesh M.,Sasaki, Takehiko,Bhanage, Bhalchandra M.

, p. 1803 - 1809 (2014)

This work reports a simple and highly efficient protocol for chemoselective transfer hydrogenation of α,β-unsaturated carbonyls using immobilized palladium metal-containing ionic liquid as a versatile heterogeneous catalyst with an excellent conversion and chemoselectivity (up to 100 %). The influence of various reaction parameters such as the effect of hydrogen donor, solvent, temperature, and time were studied. The catalyst was recycled for four consecutive cycles without significant loss in the catalytic activity. The developed protocol is more advantageous due to the use of HCOONH4 as a hydrogen source, mild reaction conditions, and simple workup procedure and applicable for a wide range of substrates.

A simple borohydride-based method for selective 1,4-conjugate reduction of α,β-unsaturated carbonyl compounds

Russo, Alyssa T.,Amezcua, Kerstin L.,Huynh, Vincent A.,Rousslang, Zach M.,Cordes, David B.

, p. 6823 - 6826 (2011)

Sodium borohydride is used in combination with a heterogeneous palladium catalyst and acetic acid to selectively reduce the carbon-carbon double bonds of various α,β-unsaturated ketones and related compounds. This simple method is most selective when non-polar solvents such as toluene are used. We observed nearly complete conversion and high selectivities using moderate catalyst loadings. The reactions were typically complete in less than 2 h.

Efficient hydrolysis of nitriles to amides with hydroperoxide anion in aqueous surfactant solutions as reaction medium

Brinchi, Lucia,Chiavini, Lisa,Goracci, Laura,Di Profio, Pietro,Germani, Raimondo

, p. 175 - 179 (2009)

Aliphatic and aromatic nitriles are converted to corresponding amides in a single step via hydrolysis with basic H2O2 in aqueous solution of the surfactant Cetyltrimethylammonium methanesulfonate (CTAOMs). The method has several advantages: use and recycle of water as reaction medium, use of environmentally benign oxidant H2O2, easy product isolation, short reaction time, high yields and selectivity, mild conditions.

Hydration of nitriles using a metal-ligand cooperative ruthenium pincer catalyst

Guo, Beibei,Otten, Edwin,De Vries, Johannes G.

, p. 10647 - 10652 (2019)

Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H2O to a wide variety of aliphatic and (hetero)aromatic nitriles in tBuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal-ligand cooperative binding of the nitrile.

An efficient and heterogeneous recyclable palladium catalyst for chemoselective conjugate reduction of α,β-unsaturated carbonyls in aqueous medium

Bagal, Dattatraya B.,Qureshi, Ziyauddin S.,Dhake, Kishor P.,Khan, Shoeb R.,Bhanage, Bhalchandra M.

, p. 1490 - 1494 (2011)

An highly efficient PS-Pd-NHC catalytic system has been developed for chemoselective conjugate reduction of α,β-unsaturated carbonyl compounds providing good to excellent conversion with remarkable chemoselectivity (up to 100%). The developed protocol is more advantageous due to use of HCOONa as hydrogen source, environmentally benign water as solvent and effective catalyst recyclability.

The hydration of nitriles catalyzed by the combination of palladium nanoparticles and copper compounds

Ishizuka, Akinori,Nakazaki, Yoshiaki,Oshiki, Toshiyuki

, p. 360 - 361 (2009)

New catalysts based on Pd nanoparticles for the hydration of nitriles to amides were investigated. Copper compounds containing oxygen acted as effective promoters in the catalytic system. The catalysts could be used to prepare aromatic and aliphatic amides from the corresponding nitriles. Chloride ions significantly inhibited the catalytic performance. Copyright

Ru(ii) complexes containing dmso and pyrazolyl ligands as catalysts for nitrile hydration in environmentally friendly media

Ferrer, íngrid,Rich, Jordi,Fontrodona, Xavier,Rodríguez, Montserrat,Romero, Isabel

, p. 13461 - 13469 (2013)

The synthesis of two Ru-dmso complexes containing the ligands 2-(3-pyrazolyl)pyridine (pypz-H), and pyrazole (pz-H), [RuIICl 2(pypz-H)(dmso)2], (2) and [RuIICl 2(pz-H)(dmso)3], (3), has been described. Both complexes have been fully characterized in solution through 1H-NMR and UV-Vis techniques and also in the solid state through monocrystal X-ray diffraction analysis. The redox properties of both complexes have also been studied by means of cyclic voltammetry. Exposure of 2 to visible light in acetonitrile produces a substitution of one dmso ligand by a solvent molecule generating a new complex, [RuIICl2(MeCN)(pypz-H)(dmso)] (4). Also, UV-visible spectroscopy points out that complex 2 presents a thermal and photochemical substitution of dmso ligands in aqueous solution. Finally, the reactivity of complexes 2 and 3 has been tested with regard to the hydration of nitriles using water as a single solvent, displaying good efficiency and selectivity for the corresponding amide derivatives. In general, better performance is achieved with complex 3. Reuse of these catalysts in water and glycerol has been explored for the first time in ruthenium-mediated nitrile hydration catalysis.

Formation of By-products during Sodium-Liquid Ammonia Reduction in Peptide Chemistry

Schoen, Istvan,Szirtes, Tamas,Ueberhardt, Tamas

, p. 639 - 640 (1982)

Reduction of protected model peptides by the usual excess of sodium in liquid ammonia leads to undesired by-products; the generally accepted blue colour for the end point is unnecessary for complete reduction.

Conversion of aldoximes into nitriles and amides under mild conditions

Tambara, Koujiro,Pantos, G. Dan

, p. 2466 - 2472 (2013)

A series of Pd(en)X2 salts were used as catalysts for the conversion of aldoximes into nitriles and amides. Highlights of this protocol include the use of inexpensive polar solvents, including water, and moderate reaction temperatures. A high degree of selectivity in the reaction outcome was observed when using aliphatic vs. aromatic/conjugated aldoximes. The Royal Society of Chemistry 2013.

Conjugate reduction of α,β-unsaturated carbonyl compounds promoted by nickel nanoparticles

Alonso, Francisco,Osante, I?aki,Yus, Miguel

, p. 3017 - 3020 (2006)

The system composed of nickel(II) chloride, lithium metal, a catalytic polymer-supported arene, and ethanol, has been efficiently applied to the conjugate reduction of a variety of α,β-unsaturated carbonyl compounds (ketones and carboxylic acid derivatives) under very mild reaction conditions. Georg Thieme Verlag Stuttgart.

[{Au(IPr)}2(μ-OH)]X complexes: Synthetic, structural and catalytic studies

Ramon, Ruben S.,Gaillard, Sylvain,Poater, Albert,Cavallo, Luigi,Slawin, Alexandra M. Z.,Nolan, Steven P.

, p. 1238 - 1246 (2011)

The synthesis of a series of dinuclear gold hydroxide complexes has been achieved. These complexes of type [{Au(IPr)}2(Iμ-OH)]X (X=BF 4, NTf2, OTf, FABA, SbF6; IPr=2,6- bis(disopropylphenyl)imidazol-2-ylidene; NTf2= bis(trifluoromethanesulfonyl)imidate; OTf=trifluoromethanesulfonate; FABA=tetrakis(pentafluorophenyl)borate) are easily formed in the presence of water and prove highly efficient in the catalytic hydration of nitriles. Their facile formation in aqueous media suggests they are of relevance in gold-catalyzed reactions involving water. Additionally, a series of [Au(IPr)(NCR)][BF4] (R=alkyl, aryl) complexes was synthesized as they possibly occur as intermediates in the catalytic reaction mechanism. 1H and 13C NMR data as well as key bond lengths obtained by X-ray diffraction studies are compared and reveal an interesting structure-activity relationship. The collected data indicate a negligible effect of the nature of the nitrile on the reactivity of [Au(L)(NCR)][X] complexes in catalysis.

-

King,McMillan

, p. 525 (1946)

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Sinapis phylogeny and evolution of glucosinolates and specific nitrile degrading enzymes

Agerbirk, Niels,Warwick, Suzanne I.,Hansen, Paul R.,Olsen, Carl E.

, p. 2937 - 2949 (2008)

Levels of sinalbin (4-hydroxybenzylglucosinolate) and 28 other glucosinolates were determined in leaves and roots of 20 species that were either phylogenetically close to Sinapis alba, Sinapis arvensis, or Sinapis pubescens (tribe Brassiceae, Brassicaceae), or were expected to contain arylalkyl nitrilase activity. Comparison with a molecular phylogenetic tree based on ITS DNA sequences identified two separate occurrences of sinalbin. The first in a group of species related to S. alba (including members of the genera Coincya and Kremeriella); and the second in S. arvensis, nested among sinalbin deficient species. Significant 4-hydroxyphenylacetonitrile degrading enzyme activity was found in both S. alba and S. arvensis, but in S. alba the major product was the corresponding carboxylic acid, while in S. arvensis the major product was the amide. Both investigated enzyme activities, nitrilase and nitrile hydratase, were specific, accepting only certain arylacetonitriles such as 4-hydroxy and 4-methoxyphenylacetonitrile. Only the S. alba enzyme required an oxygen in para position of the substrate, as found in sinalbin. Indole-3-acetonitrile, arylcyanides, and arylpropionitriles were poor substrates. The nitrilase activity of S. alba was quantitatively comparable to that reported in the monocot Sorghum bicolor (believed to be involved in cyanogenic glycoside metabolism). Glucosinolates derived from methionine were found in all Sinapis clades. Glucosinolate patterns suggested a complex evolution of glucosinolates in the investigated species, with several apparent examples of abrupt changes in glucosinolate profiles including chain length variation and appearance of glucosinolates derived from branched-chain amino acids. NMR data for desulfated homosinalbin, 9-methylsulphonylnonylglucosinolate, 3-methylpentylglucosinolate and related glucosinolates are reported, and a facultative connection between sinalbin and specific nitrilases is suggested.

A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes

Chatterjee, Basujit,Jena, Soumyashree,Chugh, Vishal,Weyhermüller, Thomas,Werlé, Christophe

, p. 7176 - 7185 (2021/06/30)

The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Han, Buxing,Ke, Zhengang,Li, Ruipeng,Liu, Zhimin,Tang, Minhao,Wang, Yuepeng,Zeng, Wei,Zhang, Fengtao,Zhao, Yanfei

supporting information, p. 9870 - 9875 (2021/12/27)

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

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