10544-63-5 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 10544-63-5 differently. You can refer to the following data:
1. clear colorless liquid
2. Ethyl crotonate has a powerful, sour, caramellic-fruity odor.
Occurrence
Reported found in Fragaria vesca. Also reported found in guava fruit, guava peel, pineapple, white wine,
yellow passion fruit, fresh mango, naranjilla fruit, mussel, loganberry, apple, papaya, concord grape, strawberry, rum, cocoa, plum,
kiwifruit and other natural sources.
Uses
Crotonic Acid Ethyl Ester, is an intermediate for the preparation of various pharmaceutical compounds. It can be used for the synthesis of (+)-trans-Trikentrin A.
Preparation
By esterification of crotonic acid with ethyl alcohol in the presence of concentrated H2SO4.
Taste threshold values
Taste characteristics at 10 ppm: rum, cognac and pungent with caramellic and fruity nuances.
Synthesis Reference(s)
Journal of the American Chemical Society, 112, p. 2716, 1990 DOI: 10.1021/ja00163a038Synthetic Communications, 14, p. 701, 1984 DOI: 10.1080/00397918408059583
General Description
A clear colorless liquid with a pungent odor. Flash point 36°F. Less dense than water and insoluble in water. Vapors heavier than air.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
ETHYL CROTONATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Health Hazard
May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may 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.
Fire Hazard
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Safety Profile
Slightly toxic by
ingestion. Corrosive. An eye irritant and
lachrymator. A flammable liquid. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 10544-63-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,5,4 and 4 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 10544-63:
(7*1)+(6*0)+(5*5)+(4*4)+(3*4)+(2*6)+(1*3)=75
75 % 10 = 5
So 10544-63-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3+
10544-63-5Relevant articles and documents
Truce,Bailey jun.
, p. 1341 (1969)
TMSCl-mediated catalytic carbocupration of alkynoates: An unprecedented and remarkable effect of catalyst loading on highly selective stereochemical induction via a TMS-allenoate intermediate
Jennings, Michael P.,Sawant, Kailas B.
, p. 3201 - 3204 (2004)
The TMSCl-mediated catalytic carbocupration of alkynoates has been investigated. It has been shown that catalyst loadings as low as 30 mol% readily allow for high yields and diastereoselectivities for a series of Grignard reagents. In addition, an unprecedented and remarkable effect of catalyst loading on stereochemical induction has been observed. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins
Zhao, Huaibo,McMillan, Alastair J.,Constantin, Timothée,Mykura, Rory C.,Juliá, Fabio,Leonori, Daniele
supporting information, p. 14806 - 14813 (2021/09/18)
We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric mixtures, this approach enables, by fine-tuning of the electronic and steric properties of the cobalt catalyst, to obtain high olefin positional selectivity. This unprecedented mechanistic feature has allowed access tocontra-thermodynamic olefins, elusive by E2 eliminations.
Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene
Spielmann, Kim,De Figueiredo, Renata Marcia,Campagne, Jean-Marc
, p. 4737 - 4743 (2017/05/12)
A straightforward strategy for the syntheses of curcumene and ar-himachalene is reported. Synthetic highlights include a catalytic and asymmetric vinylogous Mukaiyama reaction and a stereospecific hydrogenolysis of a tertiary benzylic center using Pd/C or Ni/Raney catalysts. Notably, using Ni/Raney, the stereoselectivity outcome (inversion vs retention) of the hydrogenolysis depends on the tertiary benzylic alcohol substitution.
