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620-80-4

620-80-4

Identification

Synonyms:Butanoic acid, 3-oxo-2-(phenylmethylene)-, ethyl ester;ethyl 2-benzylideneacetoacetate;2-Acetyl-3-phenylacrylic acid ethyl ester;ethyl acetobenzylidene acetate;2-benzylideneacetoacetic acid ethyl ester;2-Acetyl-3-phenylpropenoic acid ethyl ester;ethyl 2-benzylidene-3-oxobutanoate;2-Benzylidene-3-oxobutanoic acid ethyl ester;2-Benzylidene-3-oxobutyric acid ethyl ester;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • 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:Crysdot
  • Product Description:Ethyl2-benzylidene-3-oxobutanoate 95+%
  • Packaging:1g
  • Price:$ 101
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:Ethyl2-benzylidene-3-oxobutanoate 95+%
  • Packaging:5g
  • Price:$ 303
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  • Manufacture/Brand:Chemenu
  • Product Description:ethyl(E)-2-benzylidene-3-oxobutanoate 95%
  • Packaging:5g
  • Price:$ 286
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-OXO-2-(PHENYLMETHYLENE)BUTANOIC ACID ETHYL ESTER 95.00%
  • Packaging:5MG
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Relevant articles and documentsAll total 101 Articles be found

Cs-Beta with an Al-rich composition as a highly active base catalyst for Knoevenagel condensation

Otomo, Ryoichi,Osuga, Ryota,Kondo, Junko N.,Kamiya, Yuichi,Yokoi, Toshiyuki

, p. 20 - 24 (2019)

Ion-exchange of an Al-rich zeolite beta, synthesized by organic structure-directing agent-free method (Beta-OF), was studied for application as a base catalyst. While the as-synthesized Beta-OF in Na-form itself had base sites and showed moderate catalyti

Knoevenagel condensation reactions catalysed by metal-organic frameworks

Burgoyne, Andrew R.,Meijboom, Reinout

, p. 563 - 571 (2013)

Functionalised metal-organic frameworks (MOFs) which contain amino groups on their secondary building units (SBUs) are basic catalysts in the Knoevenagel condensation. University of Michigan Crystalline Material-1-amine (UMCM-1-NH2), Isoreticul

TRIMETHYLCHLOROSILANE - A NEW REAGENT FOR THE KNOEVENAGEL REACTION

Zav'yalov, S. I.,Dorofeeva, O. V.,Taganova, O. K.

, p. 453 (1985)

-

On the enantioselective phosphoric-acid-catalyzed hantzsch synthesis of polyhydroquinolines

Bonne, Damien,Bressy, Cyril,Bugaut, Xavier,Constantieux, Thierry,Jean, Marion,Lemaitre, Clément,Quinonero, Ophélie,Rodriguez, Jean,Roussel, Christian,Vanthuyne, Nicolas

supporting information, p. 3394 - 3398 (2021/05/29)

A reinvestigation of a chiral phosphoric-acid-catalyzed four-component Hantzsch enantioselective synthesis of polyhydroquinolines reported in 2009 is presented. In our hands, when the reaction was performed with fidelity to the original report using a chiral enantiopure phosphoric acid catalyst, no enantioselectivity was observed. Unlike in the original report, enantioselectivity results are backed by baseline separation of the enantiomers by HPLC analyses on chiral stationary phase with UV and chiroptical detection.

Highly active hybrid mesoporous silica-supported base organocatalysts for C–C bond formation

Erigoni,Hernández-Soto,Rey,Segarra,Díaz

, p. 227 - 236 (2019/10/28)

New base hybrid catalysts, based on silyl-derivatives of molecules carrying amino, diamino, pyrrolidine, pyrazolium and imidazolium functionalities have been successfully achieved through post synthetic grafting onto M41S-type support. Different character

Process route upstream and downstream products

Process route

2-(α-<i>o</i>-toluidino-benzyl)-acetoacetic acid ethyl ester

2-(α-o-toluidino-benzyl)-acetoacetic acid ethyl ester

ethyl 2-benzylidene acetoacetate
620-80-4

ethyl 2-benzylidene acetoacetate

N-benzylidene-2-methylaniline
5877-55-4,34143-86-7

N-benzylidene-2-methylaniline

ethyl acetoacetate
141-97-9

ethyl acetoacetate

<i>o</i>-toluidine
95-53-4

o-toluidine

Conditions
Conditions Yield
bei der Destillation im Vakuum;
ethyl acetoacetate
141-97-9

ethyl acetoacetate

benzaldehyde
100-52-7

benzaldehyde

(Z)-ethyl 2-benzylidenacetoacetate
15802-62-7,15802-63-8,620-80-4

(Z)-ethyl 2-benzylidenacetoacetate

Conditions
Conditions Yield
With piperidine; acetic acid;
75%
With piperidine; In ethyl acetate; at 130 ℃; Temperature; Flow reactor;
60%
With poly(amidoamine)-grafted nanosilica (nano-PAMAM); In hexane; at 20 ℃; for 22h;
60%
With piperidine; hexanoic acid; In benzene;
With pyridine; diethylamine; at 20 ℃; for 10h;
microwave irradiation;
ethyl acetoacetate
141-97-9

ethyl acetoacetate

benzaldehyde
100-52-7

benzaldehyde

(Z)-ethyl 2-benzylidenacetoacetate
15802-62-7,15802-63-8,620-80-4

(Z)-ethyl 2-benzylidenacetoacetate

(E)-ethyl 2-benzylidene-3-oxobutanoate
15802-62-7

(E)-ethyl 2-benzylidene-3-oxobutanoate

Conditions
Conditions Yield
at 100 ℃; for 57h;
58%
With hafnium tetrakis(trifluoromethanesulfonate); In neat (no solvent); at 80 ℃; for 0.5h;
20%
21%
With piperidine; In ethanol; for 0.333333h;
Title compound not separated from byproducts;
With L-proline; In dimethyl sulfoxide; at 20 ℃;
With piperidine; acetic acid;
With L-Tryptophan; In dimethyl sulfoxide; at 20 ℃; for 8h; optical yield given as %de;
With L-proline; In dimethyl sulfoxide; at 20 ℃; optical yield given as %de; Inert atmosphere;
1.12 g
0.42 g
With silica sulfuric acid; at 20 ℃; for 8h; optical yield given as %de; Neat (no solvent);
With iodine; acetic anhydride; In 1,2-dichloro-ethane; at 80 ℃;
With alkaline protease from Bacillus licheniformis; water; In dimethyl sulfoxide; at 45 ℃; for 72h; optical yield given as %de; stereoselective reaction; Enzymatic reaction;
With copper; In dimethyl sulfoxide; at 70 ℃; for 15h; Overall yield = 23 %Chromat.; Inert atmosphere;
30 % de
With piperidine; acetic acid; In toluene; at 120 ℃; Dean-Stark;
74 % de
With cross-linked polystyrene-titanium tetrachloride complex; In neat (no solvent); at 60 ℃; for 3.5h; Overall yield = 93 %;
54.545 % de
With piperidine; acetic acid; In toluene; for 24h; Optical yield = 23.077 percent de; Dean-Stark; Reflux;
With piperidine; acetic acid; In ethanol; at 26 ℃; for 5h; Overall yield = 100percent;
37.5 % de
ethyl acetoacetate
141-97-9

ethyl acetoacetate

benzaldehyde
100-52-7

benzaldehyde

ethyl 2-benzylidene acetoacetate
620-80-4

ethyl 2-benzylidene acetoacetate

Conditions
Conditions Yield
With 2C12H30N2(2+)*Ga(3+)*7Zn(2+)*10HO3P(2-)*8H2O*F(1-); In ethanol; at 85 ℃;
99%
With (H3O)2[Cd3(9H-carbazole-2,7-dicarboxylic acid(-2H))4]·3DMF·4H2O; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere;
97%
With G/MFSiO2Cu(proline)2; at 20 ℃; for 5h; Green chemistry;
97%
With piperidine; In acetic acid; benzene; for 2h; Heating;
93%
With iridium hydroxyapatite; at 120 ℃; for 1h;
92%
With aluminum (III) chloride; In dichloromethane; at 20 ℃; for 2h;
88%
benzaldehyde; With L-proline; In dimethyl sulfoxide; at 20 ℃;
ethyl acetoacetate; In dimethyl sulfoxide; at 80 ℃;
88%
With 1-butyl-3-methylimidazolium hydroxide; at 25 - 30 ℃; for 0.333333h;
87%
With cobalt hydroxyapatite; at 80 ℃; for 0.166667h;
87%
With piperidine; acetic acid; In toluene; at 20 ℃; for 19h; Molecular sieve;
84%
With L-Tryptophan; In dimethyl sulfoxide; at 20 ℃;
81%
80%
With potassium carbonate; PEG400; at 90 ℃; for 2h;
76%
With samarium (III) iodide; In tetrahydrofuran; for 3h; Ambient temperature;
75%
With 1-(butyl-4-sulfo)-3-methylimidazolium hydrogen sulfate; In neat (no solvent); at 100 ℃; Green chemistry;
70%
With mesoporous hybrid catalyst HYB-75P-25B; In ethanol; at 79.84 ℃; for 24h; Inert atmosphere;
66%
With mesoporous MCM-41 silica-supported silylated base hybrid catalyst; In acetonitrile; at 80 ℃; for 24h; Reagent/catalyst; Catalytic behavior;
65%
With 3-aminopropyl-functionalized silica gel; In toluene; at 25 ℃; Product distribution; also 3-(N,N-dimethylamino)propyl-functionalized silica gel, unfunctionalized silica gel; other active methylene compounds, other carbonyl compounds, other temperature;
59%
With 3-aminopropyl-functionalized silica gel; In toluene; at 25 ℃; continuous-flow conditions;
59%
With urea-functionalized mesoporous polymeric catalyst; In water; at 50 ℃; for 24h;
57%
With mesoporous titanosilicate Ti-TUD-1 catalyst; In ethanol; at 20 ℃; for 6h;
54%
With piperidine; benzoic acid; In ethanol; at 20 ℃; for 18h;
54%
With chloro-trimethyl-silane; sodium iodide; In diethyl ether; acetonitrile; for 7h; 0 deg C to room temperature;
45%
With layered hybrid materials from triethoxymethylsilane modified with protonic acid; In acetonitrile; at 80 ℃; for 7h; Inert atmosphere;
23%
modified Amberlite IRC-50 resin; In benzene; for 6h; Ambient temperature;
22%
With KNO3 converted to K2O at 300°C on nanoporous Cr-organic framework (MIL-53(Cr)); In ethanol; at 70 ℃; for 1h;
20.1%
With bifunctional Fe nanoparticles implanted on p-phenylenediamine-modified reduced graphene oxide; In toluene; at 40 ℃; for 3.5h; Catalytic behavior;
20.6%
With Thiamine hydrochloride; for 1h;
10%
With piperidine; ethanol;
With hydrogenchloride; at 0 ℃;
3-(trimethoxysilyl)propan-1-amine; silica gel; In toluene; at 25 ℃;
With piperidine; In 1,4-dioxane; at 20 ℃; further method: piperidine, HOAc, benzene, reflux;
With chloro-trimethyl-silane; at 20 ℃;
With piperidine; acetic acid; In benzene; for 1h; Heating;
With piperidine; acetic acid;
With polymer-bound piperazinediium diacetate; In chlorobenzene; at 115 ℃; for 5h;
1,1'-methylenebis(3-methylpiperidine); at 20 ℃;
With pyridine; for 1h; Heating;
With gem-diamine piperidinomethane piperidium tetrafluoroborate; at 80 ℃; for 0.166667h; Inert atmosphere; neat (no solvent);
100 %Chromat.
With piperidine;
With (2-hydroxyethyl)trimethylammonium DL-threoninate; at 20 ℃; for 24h; Inert atmosphere; Neat (no solvent);
With piperidine; acetic acid; In toluene; at 20 ℃; for 19h; Molecular sieve;
Acidic conditions;
With activated Cs-Norit carbon catalyst; at 119.84 ℃; for 4h;
With sodium hydroxide; In water; at 40 ℃;
With piperidine; acetic acid; In toluene; Reflux; Inert atmosphere;
With 3C14H15N2O(1+)*O40PW12(3-); In neat (no solvent); at 70 ℃; for 20h;
With 3-aminopropyl immobilised on mesoporous silica MCM-41; In toluene; at 60 ℃; for 1h;
With zeolite TS-1; In para-xylene; at 130 ℃; for 24h; under 760.051 Torr; Reagent/catalyst; Time;
ethyl acetoacetate; With isoreticular MOF-3 catalyst; In dimethyl sulfoxide; at 79.84 ℃; Inert atmosphere;
benzaldehyde; In dimethyl sulfoxide; at 79.84 ℃; for 2.16667h; Solvent; Temperature; Reagent/catalyst; Kinetics; Inert atmosphere;
With 10 wt.percent magnetic iron oxide nanoparticles incorporating and alklylamine grafting in MCM-41; In neat (no solvent); at 119.84 ℃; Reagent/catalyst; Inert atmosphere;
With Cs-X zeolite; at 140 ℃; Reagent/catalyst;
With {[Ni4(μ6-methanetetrabenzoate)2(μ2-H2O)4(H2O)4]·10DMF·11H2O}n; In dodecane; para-xylene; at 130 ℃; under 760.051 Torr;
With strongly basic gel-type cross-linked guanidine-methylated poly(styrene-co-divinylbenzene) resin (PGX resin); In ethanol; at 70 ℃; for 4h;
83.1 %Chromat.
With halloysite; In neat (no solvent); at 70 ℃;
With Ba2(1,3,5-benzenetricarboxylate)(NO3)(N,N-dimethylformamide); In toluene; at 110 ℃;
With morpholine; In ethanol; at 20 ℃; for 24h;
1.85 g
With triethylamine; In ethanol; for 2h; Reflux;
With piperidine; In ethyl acetate; at 85 ℃; Temperature; Flow reactor;
With L-Tryptophan; In dimethyl sulfoxide; at 20 ℃;
With piperidine; acetic acid; In neat (no solvent); at 20 ℃; for 24h;
With aluminum (III) chloride; In neat (no solvent); at 20 ℃; for 0.5h; Sealed tube; Milling;
With piperidine; In dichloromethane; at 20 ℃;
With [Pb48-methanetetrabenzoate)2]; In para-xylene; at 129.84 ℃; for 8h;
With 4Pb(2+)*2C29H16O8(4-)*4H2O*5C3H7NO; In para-xylene; at 130 ℃; for 6h; under 760.051 Torr;
With piperidine; trifluoroacetic acid; In dichloromethane; Reflux;
With Na0.13Cs0.81AlSi5O12; In dimethyl sulfoxide; at 100 ℃; Reagent/catalyst; Catalytic behavior; Inert atmosphere;
With [Zn(oba)(4-bpdh)0.5]n*(DMF)1.5; In water; at 20 ℃; for 0.416667h; under 760.051 Torr; Reagent/catalyst; Catalytic behavior; Sealed tube; Green chemistry;
With piperidine; acetic acid; In benzene; Reflux; Dean-Stark;
3-acetoxy-1-ethoxy-3-phenyl-1-propyne

3-acetoxy-1-ethoxy-3-phenyl-1-propyne

(Z)-ethyl 2-benzylidenacetoacetate
15802-62-7,15802-63-8,620-80-4

(Z)-ethyl 2-benzylidenacetoacetate

Conditions
Conditions Yield
platinum(II) chloride; In dichloromethane; at 20 ℃;
81%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

benzylamine
100-46-9

benzylamine

(Z)-ethyl 2-benzylidenacetoacetate
15802-62-7,15802-63-8,620-80-4

(Z)-ethyl 2-benzylidenacetoacetate

(E)-ethyl 2-benzylidene-3-oxobutanoate
15802-62-7

(E)-ethyl 2-benzylidene-3-oxobutanoate

Conditions
Conditions Yield
benzylamine; With fluorenone imine; In toluene; at 20 ℃; for 1h;
ethyl acetoacetate; In toluene; for 48h; Reflux; Inert atmosphere;
62%
methanesulfonic acid
75-75-2,98527-29-8

methanesulfonic acid

Ethyl 2-benzylacetoacetate
620-79-1

Ethyl 2-benzylacetoacetate

ethyl 2-benzylidene acetoacetate
620-80-4

ethyl 2-benzylidene acetoacetate

ethyl 2-(((methylsulfonyl)oxy)methyl)-3-oxo-2-phenylbutanoate

ethyl 2-(((methylsulfonyl)oxy)methyl)-3-oxo-2-phenylbutanoate

Conditions
Conditions Yield
With iodosylbenzene; p-toluenesulfonylanhydride; In dichloromethane; at 20 ℃; Inert atmosphere;
81%
12%
p-toluenesulfonylanhydride
4124-41-8

p-toluenesulfonylanhydride

Ethyl 2-benzylacetoacetate
620-79-1

Ethyl 2-benzylacetoacetate

ethyl 2-benzylidene acetoacetate
620-80-4

ethyl 2-benzylidene acetoacetate

C<sub>20</sub>H<sub>22</sub>O<sub>6</sub>S

C20H22O6S

Conditions
Conditions Yield
With iodosylbenzene; In dichloromethane; at 20 ℃; Inert atmosphere;
80%
10%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Ethyl 2-benzylacetoacetate
620-79-1

Ethyl 2-benzylacetoacetate

ethyl 2-benzylidene acetoacetate
620-80-4

ethyl 2-benzylidene acetoacetate

C<sub>20</sub>H<sub>22</sub>O<sub>6</sub>S

C20H22O6S

Conditions
Conditions Yield
With iodosylbenzene; p-toluenesulfonylanhydride; In dichloromethane; at 20 ℃; Inert atmosphere;
81%
11%
Ethyl 2-benzylacetoacetate
620-79-1

Ethyl 2-benzylacetoacetate

trifluoroacetic acid
76-05-1

trifluoroacetic acid

ethyl 2-benzylidene acetoacetate
620-80-4

ethyl 2-benzylidene acetoacetate

C<sub>15</sub>H<sub>15</sub>F<sub>3</sub>O<sub>5</sub>

C15H15F3O5

Conditions
Conditions Yield
With iodosylbenzene; p-toluenesulfonylanhydride; In dichloromethane; at 20 ℃; Inert atmosphere;
81%
11%

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