58824-48-9

Basic information

• Product Name: Benzenemethanol, a-ethenyl-4-methyl-
• CAS NO: 58824-48-9
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• Mol File: 58824-48-9.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-ethenyl-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-ethenyl-4-methyl-(58824-48-9)
• EPA Substance Registry System: Benzenemethanol, a-ethenyl-4-methyl-(58824-48-9)

Safety Data

• Hazardous Substances Data: 58824-48-9(Hazardous Substances Data)

Upstream product

• 106-38-7 para-bromotoluene 
• 107-02-8 acrolein 
• 132589-36-7 1-(4-methylphenyl)prop-2-yn-1-ol 
• 104-87-0 4-methyl-benzaldehyde 
• 3536-96-7 vinylmagnesium chloride 
• 2768-02-7 (vinyl)trimethoxylsilane 
• 1826-67-1 vinyl magnesium bromide 
• 624-31-7 4-tolyl iodide 
• 589-18-4 4-Methylbenzyl alcohol 

Downstream Products

• 54636-56-5 3-bromo-1-p-tolyl-1-propene 
• 122058-30-4 4-methylcinnamyl alcohol 
• 1504-75-2 3-(4-methylphenyl)acrylaldehyde 
• 1143526-18-4 1-{4-methyl-2-[2-(triethoxysilyl)ethyl]phenyl}propan-1-one 
• 1143526-19-5 1-{4-methyl-2,6-bis[2-(triethoxysilyl)ethyl]phenyl}propan-1-one 
• 364045-34-1 1-(4-methoxyphenyl)-4-(4-methylphenyl)-1,4-butanedione 
• 360066-00-8 benzyl-(1-p-tolyl-allyl)-amine 
• 671211-61-3 C₁₂H₁₄O₃ 
• 360065-83-4 C₁₇H₁₉N 
• 1402746-00-2 (E)-4-(4-bromophenyl)-1-(4-methylphenyl)-4-hexen-1-one 
• 5012-90-8 4-methylphenyl phenethyl ketone 
• 62584-72-9 4-(3-(4-methylphenyl)-3-oxopropyl)benzonitrile 
• 1375475-02-7 (S)-N-(1-(4-methylphenyl)allyl)benzamide 

Relevant articles and documents

Microwave-Assisted 1,3-Dioxa-[3,3]-Sigmatropic Rearrangement of Substituted Allylic Carbamates: Application to the Synthesis of Novel 1,3-Oxazine-2,4-dione Derivatives

In a first instance, the effect of the microwave irradiation on the 1,3-Dioxa-[3,3]-sigmatropic rearrangement of aryl allylic carbamates was investigated. Under these new conditions, the reaction acceleration was clearly highlighted compared to convention

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.

Lanthanide-Catalyzed Tandem Addition of Amines to Cyanoalkenes: Synthesis of Cyclic Amidines

A tandem insertion of aliphatic nitriles and unactivated alkenes to the N-H bond of secondary aliphatic amines catalyzed by simple trialkyl rare-earth metal complexes was disclosed. This reaction provides a highly atom-economic and stereoselective way to a range of cyclic amidines under mild reaction conditions.

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.

Iridium-Catalyzed Asymmetric Allylic Alkylation of Deconjugated Butyrolactams

Compared with the ever-growing list of nonprochiral nucleophiles in Ir-catalyzed asymmetric allylic substitution reactions, prochiral nucleophiles are less studied. We present a new prochiral nucleophile, namely, deconjugated butyrolactam, for Ir-catalyze

Synthesis of C5-allylindoles through an iridium-catalyzed asymmetric allylic substitution/oxidation reaction sequence of N-alkyl indolines

Iridium/Br?nsted acid cooperative catalyzed asymmetric allylic substitution reactions at the C5 position of indolines have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products in good to high

Pd-Catalyzed Asymmetric Acyl-Carbamoylation of an Alkene to Construct an α-Quaternary Chiral Cycloketone

Herein, we report the palladium-catalyzed asymmetric acyl-carbamoylation of an alkene by employing thioesters as the acyl electrophiles and t-BuNC as the carbamoyl reagent, affording an α-quaternary chiral cycloketone in synthetically useful yields with excellent enantioselectivity. The reaction proceeded via asymmetric 1,2-migratory insertions of acyl-Pd into alkenes and subsequent migratory insertion of isocyanides into C(sp3)-PdII. The product could be diversified to some valuable skeletons with retention of enantiopurity, demonstrating the synthetic utility of this protocol.

[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