622-97-9 Usage
Chemical Properties
CLEAR COLOURLESS TO LIGHT YELLOW LIQUID
Uses
4-Methylstyrene is used as a monomer for polyesters and in plastics production. It is also used as an intermediate in paint and coating additives. Further, it is used with other vinyltoluene isomers (3-vinyltoluene) as monomers for the preparation of poly(vinyltoluene). In addition to this, it is employed as a bi- ligand in the preparation of cationic, two-coordinate triphenylphosphine-gold(I)-pi complexes. Further, it is involved in Heck coupling reactions with chlorobenzene.
General Description
A clear colorless liquid with an aromatic odor. Flash point 129°F. Usually shipped with an inhibitor such as tert-butyl catechol added May polymerize if contaminated or subjected to heat. If polymerization takes place inside a closed container, the container may rupture violently. Vapors irritate the mucous membranes. Less dense than water and insoluble in water. Hence floats on water. Density is 7.6 lb / gal. Used in making plastics, especially as a monomer for polyesters.
Air & Water Reactions
Flammable. Insoluble in water.
Reactivity Profile
4-Methylstyrene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. May undergo autoxidation upon exposure to the air to form peroxides. These peroxides and polyperoxides are usually extremely unstable and liable to detonation. The peroxidation of butadiene has been involved in several serious industrial accidents.
Health Hazard
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Purification Methods
Purify it as the above styrenes and add a small amount of antioxidant if it is to be stored. It has UV in EtOH at max 285nm (log 3.07), and in EtOH + HCl 295nm (log 2.84) and 252nm (log 4.23). [Schwartzman & Carson J Am Chem Soc 78 322 1956, Joy & Orchin J Am Chem Soc 81 305 1959, Buck et al. J Chem Soc 23771949, Beilstein 5 IV 1369.]
Check Digit Verification of cas no
The CAS Registry Mumber 622-97-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 2 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 622-97:
(5*6)+(4*2)+(3*2)+(2*9)+(1*7)=69
69 % 10 = 9
So 622-97-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H10/c1-3-9-6-4-8(2)5-7-9/h3-7H,1H2,2H3
622-97-9Relevant articles and documents
Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B
Chen, Jingyun,Chen, Shufang,Jiang, Jun,Lu, Qianqian,Shi, Liyang,Xu, Zekun,Yimei, Zhao
supporting information, (2021/11/09)
A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.
Indene formation upon borane-induced cyclization of arylallenes, 1,1-carboboration, and retro-hydroboration
Hasenbeck, Max,Wech, Felix,Averdunk, Arthur,Becker, Jonathan,Gellrich, Urs
supporting information, p. 5518 - 5521 (2021/06/12)
We herein report the reaction of arylallenes with tris(pentafluorophenyl)borane that yields pentafluorophenyl substituted indenes. The tris(pentafluorophenyl)borane induces the cyclization of the allene and transfers a pentafluorophenyl ring in the course of this reaction. A Hammett plot analysis and DFT computations indicate a 1,1-carboboration to be the C-C bond-forming step.
Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes
Jiang, Yimin,Shi, Zhaojiang,Wu, Jinnan,Wu, Shaofen,Ye, Keyin,Yu, Yi,Yuan, Yaofeng
supporting information, (2021/11/17)
Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.