402-50-6 Usage
Description
4-(Trifluoromethyl)styrene, also known as α,α,α-trifluoro-4-vinyltoluene, is an organic compound that belongs to the family of styrene derivatives. It is characterized by the presence of a trifluoromethyl group attached to the 4-position of the styrene molecule. 4-(TRIFLUOROMETHYL)STYRENE exhibits a clear light yellow liquid appearance and is known for its unique chemical properties, making it a versatile building block in the synthesis of various organic compounds.
Uses
Used in Chemical Synthesis:
4-(Trifluoromethyl)styrene is used as an organic chemical synthesis intermediate for the production of a wide range of compounds. Its unique structure, which includes the electron-withdrawing trifluoromethyl group and the vinyl group, allows it to participate in various chemical reactions, such as electrophilic substitution, free radical reactions, and cross-coupling reactions. This versatility makes it a valuable starting material for the synthesis of pharmaceuticals, agrochemicals, and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(trifluoromethyl)styrene is used as a key intermediate in the synthesis of various drug molecules. The trifluoromethyl group is known to enhance the lipophilicity, metabolic stability, and overall bioactivity of the resulting compounds. As a result, 4-(trifluoromethyl)styrene plays a crucial role in the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
4-(Trifluoromethyl)styrene is also utilized in the agrochemical industry for the synthesis of novel pesticides and insecticides. The introduction of the trifluoromethyl group into the molecular structure can lead to enhanced biological activity and selectivity, making it an attractive option for the development of more effective and environmentally friendly agrochemicals.
Used in Advanced Materials:
In the field of advanced materials, 4-(trifluoromethyl)styrene is employed as a building block for the synthesis of various polymers and materials with unique properties. The incorporation of the trifluoromethyl group can significantly alter the physical and chemical properties of the resulting materials, such as their thermal stability, mechanical strength, and optical properties. This makes 4-(trifluoromethyl)styrene a valuable component in the development of innovative materials for applications in electronics, optics, and other high-tech industries.
Synthesis Reference(s)
Synthetic Communications, 18, p. 1795, 1988 DOI: 10.1080/00397918808060934
Check Digit Verification of cas no
The CAS Registry Mumber 402-50-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,0 and 2 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 402-50:
(5*4)+(4*0)+(3*2)+(2*5)+(1*0)=36
36 % 10 = 6
So 402-50-6 is a valid CAS Registry Number.
402-50-6Relevant articles and documents
Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes
Tran, Hai N.,Stanley, Levi M.
supporting information, p. 395 - 399 (2021/12/27)
The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.
Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids
Bai, Junxue,Li, Miao,Zhou, Cong,Sha, Yu,Cheng, Jiang,Sun, Jianwei,Sun, Song
supporting information, p. 9654 - 9658 (2021/12/14)
A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.
Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers
Shon, Jong-Hwa,Kim, Dooyoung,Rathnayake, Manjula D.,Sittel, Steven,Weaver, Jimmie,Teets, Thomas S.
, p. 4069 - 4078 (2021/04/06)
Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylationviaradical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.
