220583-39-1

Basic information

• Product Name: 4-[Hydroxy(4-Methylphenyl)Methyl]benzonitrile
• Synonyms: 4-[Hydroxy(4-Methylphenyl)Methyl]benzonitrile;4-(Hydroxy(p-tolyl)methyl)benzonitrile
• CAS NO: 220583-39-1
• Molecular Formula: C15H13NO
• Molecular Weight: 223.26982
• Mol File: 220583-39-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-[Hydroxy(4-Methylphenyl)Methyl]benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[Hydroxy(4-Methylphenyl)Methyl]benzonitrile(220583-39-1)
• EPA Substance Registry System: 4-[Hydroxy(4-Methylphenyl)Methyl]benzonitrile(220583-39-1)

Safety Data

• Hazardous Substances Data: 220583-39-1(Hazardous Substances Data)

Upstream product

• 623-26-7 terephthalonitrile 
• 589-18-4 4-Methylbenzyl alcohol 
• 104-87-0 4-methyl-benzaldehyde 
• 105-07-7 4-cyanobenzaldehyde 
• 5720-05-8 4-methylphenylboronic acid 

Relevant articles and documents

Electrochemical Arylation of Aldehydes, Ketones, and Alcohols: from Cathodic Reduction to Convergent Paired Electrolysis

Arylation of carbonyls, one of the most common approaches toward alcohols, has received tremendous attention, as alcohols are important feedstocks and building blocks in organic synthesis. Despite great progress, there is still a great gap to develop an ideal arylation method featuring mild conditions, good functional group tolerance, and readily available starting materials. We now show that electrochemical arylation can fill the gap. By taking advantage of synthetic electrochemistry, commercially available aldehydes (ketones) and benzylic alcohols can be readily arylated to provide a general and scalable access to structurally diverse alcohols (97 examples, >10 gram-scale). More importantly, convergent paired electrolysis, the ideal but challenging electrochemical technology, was employed to transform low-value alcohols into more useful alcohols. Detailed mechanism study suggests that two plausible pathways are involved in the redox neutral α-arylation of benzylic alcohols.

Dual-Role Catalysis by Thiobenzoic Acid in Cα-H Arylation under Photoirradiation

Thiobenzoic acid (TBA) can serve as a single-electron reducing agent under photoirradiation from a blue light-emitting diode, in the presence of appropriate electron acceptors, and the resulting sulfur-centered radical species undergoes hydrogen atom abstraction. This dual-role catalysis by TBA enables regioselectivie Cα-H arylation of benzylamines, benzyl alcohols, and ethers, as well as dihydroimidazoles, with cyano(hetero)arenes in good yield, without the need for a transition-metal photocatalyst and/or synthetically elaborated organic dyes.

Visible-Light-Triggered Directly Reductive Arylation of Carbonyl/Iminyl Derivatives through Photocatalytic PCET

The first visible-light-mediated radical-radical cross-coupling strategy that enables the direct arylation of carbonyl/iminyl derivatives in the presence of Et3N has been realized. Such an atom-economical protocol furnishes a broad scope of arylation products such as secondary/tertiary alcohols and amines via a PCET process that facilitates the challenging reduction of C-X (X = O, N). Mechanistic investigation indicates two photocatalytic redox cycles were involved in the process, and Et3N was proved to serve as a dual reductant and proton donor. Moreover, the isolated byproducts and controlled experiments could be considered as powerful supporting evidence for our hypothesis.

Recyclable and reusable Pd(OAc)2/P(1-Nap)3/[bmim][PF6]/H2O system for the addition of arylboronic acids to aldehydes

A stable and efficient Pd(OAc)2/P(1-Nap)3[tri(1-naphthyl)phosphine] catalytic system for the addition of arylboronic acids to aldehydes has been developed. In the presence of Pd(OAc)2 and P(1-Nap)3, the addition reaction of arylboronic acids with aldehydes was carried out smoothly at 65 °C to give a variety of carbinol derivatives in good to excellent yields using a mixture of [bmim][PF6] and water as the solvent. The isolation of the products was readily performed by the extraction with diethyl ether, and the Pd(OAc)2/P(1-Nap)3/[bmim][PF6]/H2O system could be easily recycled and reused six times without significant loss of catalytic activity. Our system not only avoids the use of easily volatile THF or toluene as solvent but also solves the basic problem of palladium catalyst and these phosphine ligand reuse.

A general strategy for organocatalytic activation of c-h bonds via photoredox catalysis: Direct arylation of benzylic ethers

Direct C-H functionalization and arylation of benzyl ethers has been accomplished via photoredox organocatalysis. The productive merger of a thiol catalyst and a commercially available iridium photoredox catalyst in the presence of household light directly affords benzylic arylation products in good to excellent yield. The utility of this methodology is further demonstrated in direct arylation of 2,5-dihydrofuran to form a single regioisomer.

Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with α,β-unsaturated ketones, aldehydes, and α-ketoesters

(Chemical Equation Presented) Anionic four-electron donor-based palladacycle-catalyzed 1,4-additions of arylboronic acids with α,β-unsaturated ketones and 1,2-additions of arylboronic acids with aldehydes and α-ketoesters are described. Our study demonstrated that palladacycles were highly efficient, practical catalysts for these addition reactions. The work described here not only opened a new paradigm for the application of palladacycles, but may also pave the road for other metalacycles as practically useful catalysts for such addition reactions including asymmetric ones.

Polymer-supported N-heterocyclic carbene-rhodium complex catalyst for the addition of arylboronic acids to aldehydes

A novel polymer-supported N-heterocylic carbene (NHC)-rhodium complex was prepared from chloromethyl polystyrene (CM PS) resin using a simple procedure. This polymer-supported NHC-rhodium complex was used as a catalyst for the addition of arylboronic acids to aldehydes affording arylmethanols in excellent yields.

Metal-catalyzed release of supported boronic acids for C-C bond formation

matrix presented The viability of solid-supported boronic acids as reagents for Suzuki couplings and nucleophilic additions to aldehydes and enones was successfully demonstrated. This metal-catalyzed cleavage strategy allows the synthesis of a series of functionalized biphenyl products, benzylic alcohols, and β-substituted ketones.

Rhodium-catalyzed addition of organoboronic acids to aldehydes

Highly inert to ionic additions to aldehydes, aryl- and 1- alkenylboronic acids succumb to a catalytic variant mediated by a [Rh(acac)(CO)2]-diphosphane complex in aqueous phase at 80-95°C to yield secondary alcohols [Eq. (a)]. A key step in the catalytic cycle is the transmetalation between the boron reagent and the rhodium complex. L(n) = diphosphane (e.g. 1,1'-bis(diphenylphosphanyl)ferrocene); R = aryl, 1- alkenyl; R'= alkyl, aryl; acac = acetylacetonate.