89295-32-9 Usage
Description
ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE is a chemical compound that serves as an intermediate in the synthesis of various organic compounds. It is characterized by its unique structure, which includes an ethyl group, a phenylsulfonyl group, and an acrylate group. ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE plays a crucial role in the development of new chemical entities and materials.
Uses
Used in Chemical Synthesis:
ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE is used as a key intermediate in the synthesis of ethyl 2-[(1S,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]methylacrylate. This synthesis involves a radical allylation of β-alkylcatecholboranes, which is an important reaction in organic chemistry for the formation of carbon-carbon bonds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE may be utilized in the development of new drugs and drug candidates. Its unique structure and reactivity can be harnessed to create novel molecules with potential therapeutic applications.
Used in Material Science:
ETHYL-(2-PHENYLSULFOMETHYL)-ACRYLATE can also be employed in the field of material science, where it may be used to synthesize new polymers or other materials with specific properties. These materials could have applications in various industries, such as coatings, adhesives, or even in the development of new electronic devices.
Synthesis
Ethyl 2-((phenylsulfonyl)methyl)acrylate is synthesized from ethyl 2-(bromomethyl)acrylate.Step: To a solution of ethyl 2-(bromomethyl)acrylate (1.99 g, 10.4 mmol) in dry methanol (25 mL) was added sodium phenylsulfinate (2.50 g, 15.2 mmol). After 2.5 h of reflux the mixture was concentrated under reduced pressure, the obtained residue was dissolved in EtOAc and the mixture was washed with water, brine, dried with Na2SO4, filtered and the filtrate was evaporated and purified by chromatography (50% EtOAc/Petroleum ether) to give 35 as a viscous oil: Yield (1.94 g, 74%);1H NMR (400 MHz, CDCl3) δ 7.86 (d, J = 7.6 Hz, 2H), 7.64 (t, J = 7.6 Hz, 1 H), 7.54 (t, J = 7.6 Hz, 2H), 6.51 (s, 1H), 5.92(s, 1H), 4.17(s, 2H), 4.01(q, J = 7.2 Hz, 2H), 1.17(t, J = 7.2 Hz, 3H); 13C NMR (400 MHz, CDCl3) 164.73, 138.38, 133.86, 133.33, 129.11, 129.04, 128.77, 61.48, 57.52, 14.00.
Check Digit Verification of cas no
The CAS Registry Mumber 89295-32-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,9,2,9 and 5 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 89295-32:
(7*8)+(6*9)+(5*2)+(4*9)+(3*5)+(2*3)+(1*2)=179
179 % 10 = 9
So 89295-32-9 is a valid CAS Registry Number.
89295-32-9Relevant articles and documents
Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF2-allyl bonds
Wang, Pingyang,Du, Pengcheng,Sun, Qianqian,Zhang, Jianhua,Deng, Hongmei,Jiang, Haizhen
supporting information, p. 2023 - 2029 (2021/03/16)
An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.
Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer
Liang, Lei,Guo, Ge,Li, Chen,Wang, Song-Lin,Wang, Yue-Hui,Guo, Hai-Ming,Niu, Hong-Ying
supporting information, p. 8575 - 8579 (2021/11/13)
We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst
Photoredox-Coupled F-Nucleophilic Addition: Allylation of gem-Difluoroalkenes
Liu, Haidong,Ge, Liang,Wang, Ding-Xing,Chen, Nan,Feng, Chao
supporting information, p. 3918 - 3922 (2019/02/19)
A novel strategy for the expedient construction of CF3-embeded tertiary/quarternary carbon centers was developed by taking advantage of photoredox catalysis. Thanks to a key step of single-electron oxidation, electron-rich gem-difluoroalkenes, which otherwise are essentially reluctant towards F-nucleoplilic addition, now readily participate in this fluoroallylation reaction. Furthermore, this strategy provides an elegant example for the generation, as well as functionalization, of α-CF3-substituted benzylic radical intermediates using cheap and readily available starting materials.
