515-84-4 Usage
Description
Ethyl trichloroacetate is a colorless liquid with a menthol-like odor, known for its miscibility with ethanol, ether, and benzene, but insolubility in water. It is a versatile chemical compound that undergoes atom-transfer radical addition reactions, particularly with styrene when catalyzed by Ru-pentamethylcyclopentadienyl complexes.
Uses
Used in Organic Synthesis:
Ethyl trichloroacetate is used as a key intermediate in the synthesis of various organic compounds, including dichlorocarbon precursors and phenyl(trichloromethyl)methyl. Its reactivity and compatibility with other chemicals make it a valuable component in creating complex molecular structures.
Used in Pharmaceutical Industry:
Ethyl trichloroacetate serves as an important intermediate in the pharmaceutical sector, contributing to the development of new drugs and medications. Its unique chemical properties allow it to be a part of the synthesis process for various pharmaceutical compounds.
Used as a Solvent:
Due to its miscibility with several organic solvents, Ethyl trichloroacetate is used in various applications where a suitable solvent is required. Its ability to dissolve a wide range of substances makes it a preferred choice in different industries.
Used in Perfumery:
Ethyl trichloroacetate is also utilized in the perfume industry, where it plays a role in the creation of various fragrances. Its unique odor and compatibility with other aromatic compounds contribute to its use in this application.
Preparation
Ethyl trichloroacetate is synthesized from trichloroacetic acid and ethyl alcohol by the esterification reaction. synthesis steps: Trichloroacetic acid(TCA), anhydrous ethyl alcohol and sulfuric acid are heated together and refluxed for 6 h. After cooling, the ester layer is separated by pouring into water, neutralized with 5-10% sodium carbonate solution, washed with water and dried overnight with anhydrous calcium chloride. After filtration, distillation was carried out to obtain the finished product. Yield 75%.
Synthesis Reference(s)
The Journal of Organic Chemistry, 46, p. 3519, 1981 DOI: 10.1021/jo00330a028
Purification Methods
Shake the ester with saturated aqueous Na2CO3 (three times), aqueous 50% CaCl2 (three times), saturated aqueous NaCl (twice), then distil over CaCl2 and redistil it under reduced pressure. [Beilstein 2 IV 514.]
Check Digit Verification of cas no
The CAS Registry Mumber 515-84-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 5 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 515-84:
(5*5)+(4*1)+(3*5)+(2*8)+(1*4)=64
64 % 10 = 4
So 515-84-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H5Cl3O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
515-84-4Relevant articles and documents
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Sokolskii,Knunjanz
, (1965)
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Alkyl Halides via Visible Light Mediated Dehalogenation
Rathnayake, Manjula D.,Weaver, Jimmie D.
supporting information, p. 9681 - 9687 (2019/11/28)
Net selective bromination and chlorination of activated C-H bonds can be effected in generally high yield via a simple perhalogenation/dehalogenation sequence. The photochemical reductions require no photocatalyst, relying instead on the formation of an electron donor-acceptor complex of the substrate and reductant, or alternatively autophotocatalysis. Some reactions proceed despite any apparent photon absorption, serving as a cautionary tale for other photochemical reactions involving amines. Mechanistic experiments provide an explanation for this observation.
Efficient partial hydrogenation of trichloromethyl to gem-dichloromethyl groups in platinum on carbon-catalyzed system
Sawama, Yoshinari,Imanishi, Takahiro,Nakatani, Ryosuke,Fujiwara, Yuta,Monguchi, Yasunari,Sajiki, Hironao
supporting information, p. 4540 - 4546 (2014/06/10)
While gem-dichloromethyl groups can be directly synthesized by the mono-dechlorination of the corresponding trichloromethyl groups, the suppression control of the over-reduction to form chloromethyl or methyl functionalities is quite difficult. We have established the efficient and widely applicable mono-dechlorination method of the trichloromethyl groups to form the corresponding gem-dichloromethyl groups using platinum on carbon in dimethylacetamide as a specific solvent at 25 °C under a hydrogen atmosphere. The mono-dechlorination of the α,α,α- trichloromethylcarbonyl groups smoothly proceeded by the use of platinum on carbon as a catalyst in a highly chemoselective manner, while the efficient mono-dechlorination of the alkyl- and aryl-trichloromethyl groups required the combined use of Bu3SnH.
New method of synthesis of acetals containing phosphorus in the alcohol fragment
Gazizov,Safina,Khairullin,Gazizov
, p. 311 - 312 (2007/10/03)
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