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Cas Database

2021-28-5

2021-28-5

Identification

  • Product Name:Benzenepropanoic acid, ethyl ester

  • CAS Number: 2021-28-5

  • EINECS:217-966-6

  • Molecular Weight:178.231

  • Molecular Formula: C11H14O2

  • HS Code:29163900

  • Mol File:2021-28-5.mol

Synonyms:Benzenepropanoic acid,ethyl ester;Hydrocinnamicacid, ethyl ester (6CI,8CI);3-Phenylpropanoic acid ethyl ester;3-Phenylpropionic acid ethyl ester;Ethyl benzenepropanoate;Ethyl dihydrocinnamate;Ethylhydrocinnamate;NSC 126040;

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Safety information and MSDS view more

  • Signal Word:No signal word.

  • Hazard Statement:none

  • 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.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 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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  • Manufacture/Brand:TRC
  • Product Description:Ethyl 3-Phenylpropionate
  • Packaging:250g
  • Price:$ 240
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Ethyl 3-Phenylpropionate >98.0%(GC)
  • Packaging:25g
  • Price:$ 32
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Ethyl 3-Phenylpropionate >98.0%(GC)
  • Packaging:250g
  • Price:$ 223
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl 3-Phenylpropionate ≥98%, FG
  • Packaging:250g
  • Price:$ 203
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl 3-Phenylpropionate ≥98%, FG
  • Packaging:1kg
  • Price:$ 528
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl 3-Phenylpropionate ≥98%,FG
  • Packaging:1 SAMPLE
  • Price:$ 50
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl 3-Phenylpropionate ≥98%, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Ethyl hydrocinnamate 99%
  • Packaging:25g
  • Price:$ 45
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Ethyl 3-Phenylpropionate
  • Packaging:250 g
  • Price:$ 800
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:Ethyl 3-Phenylpropionate
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Relevant articles and documentsAll total 334 Articles be found

Sugi,Bando

, p. 727,728-730 (1976)

Chitosan as biosupport for the MW-assisted synthesis of palladium catalysts and their use in the hydrogenation of ethyl cinnamate

Raspolli Galletti, Anna Maria,Antonetti, Claudia,Bertoldo, Monica,Piccinelli, Fabio

, p. 95 - 101 (2013)

A novel catalytic system based on palladium supported on chitosan was synthesized adopting a MW-assisted process. This synthetic approach results efficient under mild reaction conditions and very short microwave irradiation times. The prepared catalyst was employed in the hydrogenation of ethyl cinnamate (EC) to ethyl hydrocinnamate (EHC) adopting both traditional heating and MW irradiation: this is the first study on this reaction which involves this type of catalyst. In addition, a one pot fully MW-assisted process which provides the synthesis of the Pd/chitosan catalyst and its direct use in the hydrogenation of ethyl cinnamate has been also studied. This one pot procedure assures fast reaction rate under mild reaction conditions avoiding the catalyst's isolation and purification, thus making easier the reaction scale-up. The achieved yields in the target product are particularly good and the system results completely recyclable, due to the stabilizing effect of the functionalized natural support toward the palladium particles.

Peripherally cyclometalated iridium complexes of dipyridylporphyrin

Yoshida, Keita,Nakashima, Takumi,Yamaguchi, Shigeru,Osuka, Atsuhiro,Shinokubo, Hiroshi

, p. 8773 - 8775 (2011)

Two types of novel iridium pincer complexes bearing a porphyrin backbone were synthesized and characterized from dipyridylporphyrin. One of the complexes has a Lewis acidic site on the iridium center in the mer-coordination mode. The other complex takes the fac-coordination, which is rarely observed in benzene-based pincer complexes. The Royal Society of Chemistry 2011.

A Simple, Effective, New, Palladium-Catalyzed Conversion of Enol Silanes to Enones and Enals

Larock, Richard C.,Hightower, Timothy R.,Kraus, George A.,Hahn, Pat,Zheng, Deye

, p. 2423 - 2426 (1995)

Enol silanes derived from aldehydes and ketones are readily converted to the corresponding α,β-unsaturated carbonyl compounds by 10percent Pd(OAc)2 in the presence of one atmosphere of oxygen in DMSO as the solvent.

A mild method for protodesilylation of α-dimethylphenylsilyl ester substrates

Poliskie, G. Michelle,Mader, Mary M.,Van Well, Renate

, p. 589 - 592 (1999)

Mild conditions (1.2 eq. Hg(OAc)2, 1.2 eq. TBAF in 1:1 MeOH/THF; 35 min at 0 °C) have been developed for the protodesilylation of α- dimethylphenylsilyl esters. An enolate-dependent mechanism for the reaction was supported through studies indicating the clean incorporation of deuterium. To further investigate the mechanism, the optimal conditions as well as the kinetics of the reaction were explored.

Synthesis of flavor compound ethyl hydrocinnamate by Yarrowia lipolytica lipases

Zieniuk, Bart?omiej,Fabiszewska, Agata,Wo?oszynowska, Ma?gorzata,Bia?ecka-Florjańczyk, Ewa

, p. 455 - 464 (2021)

Two biocatalysts with high lipolytic activity were obtained–freeze-dried supernatant and freeze-dried biomass of Yarrowia lipolytica KKP 379. The biocatalysts were compared with Candida antarctica lipase B in the synthesis of ethyl hydrocinnamate–a flavour compound with a floral-honey aroma. Ester synthesis was completed after 2 h when 3 grams of freeze-dried biomass was used. Using smaller amounts of biomass (1.2 and 0.6 g) also allowed to achieve high ester conversion and results were comparable with those obtained for CALB used as a catalyst. Freeze-dried supernatant showed a weaker lipase activity (22.17 U/g) compared to freeze-dried biomass (46.13 U/g), which resulted in a lower conversion of 3-phenylpropionic acid to its ethyl ester, and after 36 h a conversion peaked at around 70%, then began to decrease and finally the conversion reached 50%. Moreover, antimicrobial and antioxidant properties of the synthesised ester were evaluated. Ethyl hydrocinnamate showed no antibacterial activity and weak antioxidant activity towards DPPH radical. In contrast to bacteria, the obtained compound moderately inhibited the growth of tested yeast species, where inhibition zones ranged from 10 to 16 mm.

-

Ono,Hayashi

, p. 11,12 (1953)

-

Structural features and catalytic reactivity of [Pd{(Ph2P)2N(CH2)3Si(OCH3)3-κP,P′}I2] and related complexes in hydroalkoxycarbonylation and Suzuki–Miyaura C?C cross-coupling reactions

Stamatopoulos, Ioannis K.,Kapsi, Maria,Roulia, Maria,Vougioukalakis, Georgios C.,Raptopoulou, Catherine P.,Psycharis, Vassilis,Kostas, Ioannis D.,Kollár, László,Kyritsis, Panayotis

, p. 292 - 298 (2018)

The synthesis, as well as the structural and spectroscopic characterization of the palladium(II) complex [Pd{(Ph2P)2N(CH2)3Si(OCH3)3-κP,P′}I2], bearing the bis(phosphino)amine ligand (P,P) = (Ph2P)2N(CH2)3Si(OCH3)3, is described. X-ray crystallography studies revealed a square planar PdP2I2 coordination sphere, the structural features of which are compared with those of analogous nickel(II), palladium(II) and platinum(II) complexes. The three complexes [Pd(P,P)X2], X = Cl, Br, I, along with [Pd{(Ph2P)2N((S)-CHPhMe)-κP,P′}Cl2] and [Pd{(Ph2PSe)(Ph2P)N((S)-CHMePh)-κP,Se}Cl2], were tested as catalysts in homogeneous hydroalkoxycarbonylation reactions. The hydroalkoxycarbonylation of styrene proved to be perfectly regioselective towards the branched ester. Complex [Pd(P,P)Cl2] showed remarkably higher activity compared with that of [Pd(P,P)X2], X = Br, I. Furthermore, complex [Pd(P,P)I2] was studied as a homogeneous catalyst precursor in the Suzuki–Miyaura C?C coupling reaction between aryl bromides and phenylboronic acid. Complex [Pd(P,P)I2] was immobilized onto STx–1 montmorillonite clay and the catalytic reactivity of the heterogenized catalyst was also investigated in both hydroalkoxycarbonylation and Suzuki–Miyaura reactions.

Palladium(0) nanoparticles on glass-polymer composite materials as recyclable catalysts: A comparison study on their use in batch and continuous flow processes

Mennecke, Klaas,Cecilia, Raul,Glasnov, Toma N.,Gruhl, Susanne,Vogt, Carla,Feldhoff, Armin,Vargas, M. A. Larrubia,Kappe, C. Oliver,Kunz, Ulrich,Kirschninga, Andreas

, p. 717 - 730 (2008)

Palladium particles were generated by reduction of palladate anions bound to an ion exchange resin inside microreactors. The size and distribution of the palladium particles differed substantially depending on the degree of cross-linking and the density of ion exchange sites on the polymer/glass composites, the latter parameter having a larger influence than the former. The polymer phase of the composite materials was used for the loading with clusters composed of palladium particles which are 1 to 10 nm in diameter. The reactivity and stability of six different palladium-doped polymer/glass composite samples for transfer hydrogenations was investigated both under conventional and microwave heating in the batch mode as well as under continuous flow conditions using the cyclohexene-promoted transfer hydrogenation of ethyl cinnamate as a model reaction. Regarding the heating method it was found that catalysts that are composed of larger metal particles perform better under microwave irradiating conditions whereas samples with smaller particle sizes perform better under conventional heating. Comparing batch experiments with flow-through experiments the latter technique gives better conversion. Reusability was better in microwave heated experiments than in traditional heating.

Synthesis of Carboxylic Acids and Esters Using Polymer-Bound Oxazolines

Colwell, Arthur R.,Duckwall, Louis R.,Brooks, Reda,McManus, Samuel P.

, p. 3097 - 3102 (1981)

2,4-Dimethyl-4-(hydroxymethyl)-2-oxazoline was attached to cross-linked polystyrene, giving the polymer-bound oxazoline 3.Alkylation of 3, followed by hydrolysis or ethanolysis, provided α and α,α' mono- and dialkylated acetic acids or their ethyl esters

Catalyst type and concentration dependence in catalytic transfer hydrogenolysis of α,β-unsaturated carbonyls and nitriles via ammonium formate

Ram,Spicer

, p. 2683 - 2690 (1992)

The catalytic reduction of a variety of α,β-unsaturated compounds into saturated analogs in the presence of other reducible moieties is described using ammonium formate as a hydrogen source. The rate dependence on the concentration of Pd-C catalyst as well as on 5% Pd-BaSO4 and Ra-Ni are also characterized.

-

Newman,Walborsky

, p. 4296 (1950)

-

The relative reactivities of various unsaturated compounds towards diisopropyloxy(η2-cyclopentene)titanium

Cadoret, Frédéric,Six, Yvan

, p. 5491 - 5495 (2007)

Competition experiments were performed by adding pre-formed solutions of diisopropyloxy(η2-cyclopentene)titanium in diethyl ether to various mixtures of unsaturated compounds at low temperature, establishing the following reactivity scale: aldehyde > nitrile > ketone > terminal alkyne > internal alkyne > terminal alkene > ester, carbonate.

Reduction of ethyl t-cinnamates by samarium diiodide

Lin, Tzuen-Yeuan,Fuh, Ming-Ren,Chan, I-San

, p. 843 - 847 (2001)

Rate constants directly measured from the GC-analyzed method for SmI2 reduction of ethyl t-cinnamate and its substituted derivatives in the presence of HMPA and t-butanol were obtained. HMPA exhibits a stronger catalytic effect than t-butanol. Dependence of reaction rates on concentration of SmI2 and temperature were studied. Electron-donating groups retard this reduction; the electron-withdrawing groups, on the other hand, enhance the reaction rates dramatically.

Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin

Ichihara, Shuta,Ishida, Moeka,Ito, Ryo,Kato, Ayumu,Monguchi, Yasunari,Nakamura, Shinji,Park, Kwihwan,Sajiki, Hironao,Takada, Hitoshi,Wakayama, Fumika,Yamada, Tsuyoshi,Yamada, Yutaro

, p. 2702 - 2710 (2022/01/19)

We have developed a method for the esterification of carboxylic acids with alcohols using amphipathic, monolithic-resin bearing sulfonic acid moieties as cation exchange functions (monolith-SO3H). Monolith-SO3H efficiently catalyzed the esterification of aromatic and aliphatic carboxylic acids with various primary and secondary alcohols (1.55.0 equiv) in toluene at 6080 °C without the need to remove water generated during the reaction. The amphipathic property of monolith-SO3H facilitates dehydration due to its capacity for water absorption. This reaction was also applicable to thioesterification, wherein the corresponding thioesters were obtained in excellent yield using only 2.0 equiv of thiol in toluene, although heating at 120 °C was required. Moreover, monolith-SO3H was separable from the reaction mixtures by simple filtration and reused for at least five runs without decreasing the catalytic activity.

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

Gavara, Laurent,Legru, Alice,Verdirosa, Federica,Sevaille, Laurent,Nauton, Lionel,Corsica, Giuseppina,Mercuri, Paola Sandra,Sannio, Filomena,Feller, Georges,Coulon, Rémi,De Luca, Filomena,Cerboni, Giulia,Tanfoni, Silvia,Chelini, Giulia,Galleni, Moreno,Docquier, Jean-Denis,Hernandez, Jean-Fran?ois

supporting information, (2021/06/15)

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol

Topf, Christoph,Vielhaber, Thomas

, (2021/07/10)

We communicate a user-friendly and glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated C[dbnd]C[sbnd]bonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields. The described system offers a brisk and atom-efficient access to both secondary alcohols and saturated esters avoiding the use of oxygen-sensitive and expensive phosphine-based ligands.

Chemoselective Hydrogenation of Olefins Using a Nanostructured Nickel Catalyst

Klarner, Mara,Bieger, Sandra,Drechsler, Markus,Kempe, Rhett

supporting information, p. 2157 - 2161 (2021/05/21)

The selective hydrogenation of functionalized olefins is of great importance in the chemical and pharmaceutical industry. Here, we report on a nanostructured nickel catalyst that enables the selective hydrogenation of purely aliphatic and functionalized olefins under mild conditions. The earth-abundant metal catalyst allows the selective hydrogenation of sterically protected olefins and further tolerates functional groups such as carbonyls, esters, ethers and nitriles. The characterization of our catalyst revealed the formation of surface oxidized metallic nickel nanoparticles stabilized by a N-doped carbon layer on the active carbon support.

Process route upstream and downstream products

Process route

ethanol
64-17-5

ethanol

Benzyl 3-phenylpropionate
22767-96-0

Benzyl 3-phenylpropionate

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

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

benzyl alcohol

Conditions
Conditions Yield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2]; In various solvent(s); at 150 ℃; for 16h;
100%
ethanol
64-17-5

ethanol

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

3-phenylpropionic anhydride
15781-96-1

3-phenylpropionic anhydride

Conditions
Conditions Yield
With magnesium chloride; for 2h;
82%
12%
ethanol
64-17-5

ethanol

3-(1-oxo-3-phenylpropyl)-1,3-oxazolidin-2-one
107978-04-1

3-(1-oxo-3-phenylpropyl)-1,3-oxazolidin-2-one

dimethylenecyclourethane
497-25-6

dimethylenecyclourethane

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

Conditions
Conditions Yield
With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 16h;
81%
ethyl 3-oxo-3-phenylpropionate
94-02-0

ethyl 3-oxo-3-phenylpropionate

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

Ethyl 3-hydroxy-3-phenylpropanoate
5764-85-2

Ethyl 3-hydroxy-3-phenylpropanoate

Conditions
Conditions Yield
With samarium diiodide; water; In tetrahydrofuran; at 20 ℃; for 0.00277778h;
80%
7%
With potassium hydroxide; samarium diiodide; In tetrahydrofuran; at 20 ℃; for 0.0833333h;
46%
52%
ethyl cinnamate
4192-77-2

ethyl cinnamate

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

Conditions
Conditions Yield
With NaH-alkoxide-Ni salt reagent; water; In tetrahydrofuran; at 25 ℃; for 0.25h;
81%
With chloro-trimethyl-silane; water; sodium iodide; In hexane; for 108h; Ambient temperature;
66%
27%
With tertiary butyl chloride; sodium iodide; In acetonitrile; for 24h; Yield given. Yields of byproduct given; Heating;
ethyl 3-phenyl-2-propenoate
103-36-6

ethyl 3-phenyl-2-propenoate

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

Cinnamic acid
621-82-9

Cinnamic acid

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

Conditions
Conditions Yield
With water; hydrogen iodide; In toluene; at 110 ℃; for 8h;
14 %Spectr.
12 %Spectr.
31 %Spectr.
diethyl 2-benzylmalonate
607-81-8

diethyl 2-benzylmalonate

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

Conditions
Conditions Yield
With silica gel; In acetone; at 220 ℃; for 0.5h; Inert atmosphere;
69%
ethanol
64-17-5

ethanol

(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

Conditions
Conditions Yield
With hydrogen; at 20 ℃; under 750.075 Torr;
3-phenylpropionamide
102-93-2

3-phenylpropionamide

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

dihydrocinnamonitrile
645-59-0

dihydrocinnamonitrile

Conditions
Conditions Yield
With tetraethoxy tellurium(IV); In tetrachloromethane; for 3h; Heating;
84%
7%
tetraethoxy tellurium(IV)
2017-01-8

tetraethoxy tellurium(IV)

3-phenylpropionamide
102-93-2

3-phenylpropionamide

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

dihydrocinnamonitrile
645-59-0

dihydrocinnamonitrile

Conditions
Conditions Yield
In tetrachloromethane; for 3h; Heating;
7%
84%

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