39627-62-8

Usage

Usage

Used in the production of plastics, synthetic rubber, and resins.
Versatile monomer for polymerization to form polystyrene.
Manufacture of consumer products like packaging, disposable cups and plates, and insulation materials.
Production of synthetic rubbers, latex, fiberglass, and composites.

Health Risks

Prolonged exposure linked to respiratory and neurological effects.
Considered a possible carcinogen by some regulatory agencies.

Upstream product

• 932-31-0 ortho-tolylmagnesium bromide 
• 107-02-8 acrolein 
• 14593-43-2 benzyl allyl ether 
• 1826-67-1 vinyl magnesium bromide 
• 529-20-4 2-methylphenyl aldehyde 
• 95-46-5 2-methylphenyl bromide 
• 87-24-1 ethyl 2-methylbenzoate 
• 3536-96-7 vinylmagnesium chloride 

Downstream Products

• 54636-61-2 3-(o-tolyl)prop-2-enyl bromide 
• 39627-60-6 1-(2-methylphenyl)-2-propen-1-one 
• 20850-01-5 3-(2-methylphenyl)-2-propen-1-ol 
• 945030-89-7 1-o-tolylallyl acetate 
• 115117-74-3 (E)-3-(2'-methylphenyl)-2-propen-1-ol acetate 
• 1173006-66-0 C₁₆H₁₆S 
• 1173006-67-1 C₁₆H₁₆S 
• 1240503-31-4 3-hydroxy-5,5-dimethyl-2-(1-0-tolylallyl)cyclohex-2-enone 
• 1313022-75-1 (S)-1-(1-(benzyloxy)allyl)-2-methylbenzene 
• 1370701-30-6 3-(2-bromo-4-methoxyphenyl)-1-o-tolyl-propan-1-one 
• 1370701-28-2 3-(2-bromo-4-methoxyphenyl)-1-o-tolyl-prop-2-en-1-ol 
• 93433-65-9 1-(2-methylphenyl)-3-phenyl-1-propanone 
• 1092491-52-5 3-(2-bromophenyl)-1-o-tolyl-propan-1-one 
• 1370701-27-1 3-(2-bromophenyl)-1-o-tolyl-prop-2-en-1-ol 

Relevant academic research and scientific papers

Solvent effects on OH stretching frequencies for 1-arylallyl alcohols

A series of 1-arylallyl alcohols were prepared and its OH stretching frequencies measured in 20 different non-HBD solvents at room temperature. It is noticed that the observed stretching bands were highly sensitive to the nature of the solvents. Multiple

Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol

One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.

Electrocatalytic Activation of Donor–Acceptor Cyclopropanes and Cyclobutanes: An Alternative C(sp3)?C(sp3) Cleavage Mode

We describe the first electrochemical activation of D–A cyclopropanes and D–A cyclobutanes leading after C(sp3)?C(sp3) cleavage to the formation of highly reactive radical cations. This concept is utilized to formally insert molecula

Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

Cobalt-Catalyzed Diastereo- And Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates

Catalytic generation of ambiphilic π-allyl-metal complexes and their utility in enantioselective transformations constitutes a powerful approach for introduction of allyl groups to a molecule. Herein an unprecedented cobalt-catalyzed highly site-, diastereo-, and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alcohol derivatives to diversified enantioenriched homoallylic alcohols with a remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.

[Pd]-Catalyzedpara-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols

4-[(E)-3-Arylprop-2-enyl]phenols are omnipresent scaffolds and constitute natural products and biologically significant compounds. Obtusastyrene and obtustyrene are two such phenolic-based natural products isolated fromDalbergia retusa. The development of strategies based on a site-selective allylation, particularly protecting group-free substrates and non-activated coupling agents, is indispensable in organic synthesis. Herein, we present a highly regioselective [Pd]-catalyzedpara-allylation of phenols using simple, inactivated allylic alcohols as allylating coupling partners. Notably, this strategy is successful in open-air and under mild reaction conditions. Besides, the efficacy of the present protocol was demonstrated by the direct synthesis of obtusastyrene and obtustyrene.

Nickel-Catalyzed Reductive Csp2-Csp3Cross Coupling Using Phosphonium Salts

A nickel-catalyzed reductive cross coupling with phosphonium salts and allylic C(sp3)-O bond electrophiles, which granted direct construction of the C(sp2)-C(sp3) bond, is successfully developed. The protocol features broad substrate scope, high-functional-group tolerance, and heterocycle compatibility. Notably, the much more challenging reductive cross coupling with heterocyclic thiazolylphosphonium salts has also been accomplished for the first time.

Highly efficient kinetic resolution of aryl-alkenyl alcohols by ru-catalyzed hydrogen transfer

No matter through asymmetric reduction of ketones or kinetic resolution of secondary alcohols, enantioselective synthesis of the corresponding secondary alcohols is challenging when the two groups attached to the prochiral or chiral centers are spatially

Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins

A new ruthenium-based catalytic system for branched-selective asymmetric allylic alkylation is disclosed and applied to the synthesis of chiral isatin derivatives. The catalyst, which is generated in situ from commercially available CpRu(MeCN)3PF6 and a BINOL-derived phosphoramidite, is both highly active (TON up to 180) and insensitive to air and moisture. Additionally, the N-alkylated isatins accessible using this methodology are versatile building blocks that are readily transformed into chiral analogs of achiral drug molecules.

In Situ Ring-Closing Strategy for Direct Synthesis of N-Heterocyclic Carbene Nickel Complexes and Their Application in Coupling of Allylic Alcohols with Aryl Boronic Acids

A in situ ring-closing strategy was developed for the synthesis of N-heterocyclic carbene nickel complexes. The process was carried out in air, and did not require solvent purification. The resulting nickel complexes were investigated as catalysts for the coupling of allylic alcohols with aryl boronic acids. A wide range of allylic substrates and aryl acids proved to be applicable to this catalytic system. Control experiments suggest that the Ni(0) may be the true active species in the coupling reactions. (Figure presented.).