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Usage

Uses

Used in Chemical Research:
1,1-Diphenylethanol is used as a research compound for studying the ESR (electron spin resonance) spectra of the spiro-cyclohexadienyl intermediate in alkoxyl radicals. This application is significant in understanding the behavior and properties of radicals, which are essential in various chemical reactions and processes.
Used in Pharmaceutical Industry:
1,1-Diphenylethanol can be used as a starting material or intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
1,1-Diphenylethanol is used as a building block in the synthesis of complex organic molecules. Its reactivity and functional groups make it a valuable component in the creation of new organic compounds with diverse applications.
Used in Material Science:
1,1-Diphenylethanol can be used in the development of new materials with specific properties, such as polymers, coatings, and adhesives. Its aromatic structure and functional groups contribute to the overall properties of these materials, making them suitable for various applications.

Purification Methods

Crystallise 1,1-diphenylethanol from n-heptane and/or distil it under vacuum. The benzoyl derivative has m 115o and the phenylurethane has m 119o. [Bromberg et al. J Am Chem Soc 107 83 1985, Beilstein 6 H 685, 6 I 330, 6 II 639, 6 III 3395, 6 IV 4713.]

InChI:InChI=1/C14H14O/c1-14(15,12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11,15H,1H3

Upstream product

• 60-29-7 diethyl ether 
• 625-60-5 ethyl thioacetate 
• 2186-29-0 1,1-diphenylethyl hydroperoxide 
• 985-93-3 1,2-dimethoxy-1,1,2,2-tetraphenyl-ethane 
• 127-08-2 potassium acetate 
• 141-78-6 ethyl acetate 
• 75-36-5 acetyl chloride 
• 119-61-9 benzophenone 
• 74-87-3 methylene chloride 
• 530-48-3 1,1-Diphenylethylene 
• 5558-67-8 2,2-diphenylpropionitrile 
• 10496-82-9 2,2,3,3-tetraphenylbutane 
• 917-54-4 methyllithium 
• 4460-50-8 Dipotassium benzophenone dianion 

Downstream Products

• 55141-82-7 oxalic acid bis-(1,1-diphenyl-ethyl ester) 
• 530-48-3 1,1-Diphenylethylene 
• 19244-53-2 1,1,3,3-tetraphenyl-1-butene 
• 19303-32-3 1-methyl-1,3,3-triphenylindane 
• 67640-10-2 diethyl-[2-(1,1-diphenyl-ethoxy)-ethyl]-amine 
• 38241-07-5 tert.-butyl 1,1-diphenylethyl peroxide 
• 5558-66-7 2,2-diphenylpropanoic acid 
• 24318-53-4 Benzoesaeure-α-phenyl-α-methyl-benzylester 
• 35036-32-9 1,1-diphenyl-1-ethoxyethane 
• 81194-43-6 dimethylallylsilyl 1,1-diphenylethyl ether 
• 22293-23-8 (1-azidoethane-1,1-diyl)dibenzene 
• 79506-34-6 1-<1-methyl-1-(1,1-diphenylethylperoxy)ethyl>-4-acetylbenzene 
• 54225-34-2 1-Amino-4,4-diphenyl-3-thiapentane 
• 612-00-0 1,1'-ethylidenebis-benzene 

Relevant academic research and scientific papers

Hydroxide-promoted Reduction of the Corrole Complexes of Cobalt(III) and Iron(III) in the Presence of Olefin

An oxygenation system effective for electronrich olefins which involves the hydroxide ion, provides electrons required for reduction of the corrole complexes of cobalt(III) and iron(III).

Photochemical polar addition of 1,1-diphenylethene using photosensitive surfactant in stable oil-in-water emulsion

An aq NaOH solution of the photosensitive surfactant 1 was mixed with 1,1-diphenylethene 2 to form a stable oil-in-water emulsion and excitation of the emulsion afforded the alcohol 3 in good yield without stirring. The photosensitive surfactant 1 works more efficiently in heterogeneous system (in water) than in homogeneous system (in organic solvent).

Cleavage of Si-Ar bond vs Si-Me bond: A remarkable counterion effect on reactivity

Formation of distinctly different products from the same alkoxide intermediate indicates a strong dependence of reaction pathways on counterions.

PREPARATION AND REACTIONS OF SOLVENT-FREE ARYLCALCIUM HALIDES, ArCaX (X = F, Cl, Br)

Reactions of aryl halide vapor and calcium metal vapor were found to give the corresponding arylcalcium halides, ArCaX (X = F, Cl, and Br).Phenylcalcium halide, PhCaX (X = F and Cl), reacted with trimethylchlorosilane to give phenyltrimethylsilane.The reactions of phenylcalcium halides with acetone and benzaldehyde readily gave good yields of 1-methyl-1-phenylethanol and diphenylmethanol, respectively.Phenylcalcium halides reacted slowly with acetonitrile to afford acetophenone in poor yields.With ethyl acetate, phenylcalcium halides gave a mixture of 1,1-diphenylethanol and acetophenone.

Kinetic Isotope Effect and Substituent Effect Study on the Grignard Reaction of MeMgI with Benzophenone. A Rate-Determining C-C Bond Formation

The carbonyl carbon-14 kinetic isotope effect and substituent effects were determined for the reaction of MeMgI with benzophenone.The observed large carbon isotope effect (14k/12k=1.056) together with the large steric effect on reactivity introduced by o-substituents on benzophenone indicated that the C-C bond formation is the rate-determinig step of the Grignard reaction.

To Rebound or...Rebound? Evidence for the "alternative Rebound" mechanism in Ca'H Oxidations by the systems nonheme Mn Complex/H2O2/carboxylic acid

In this work, it has been shown that aliphatic Ca'H oxidations by bioinspired catalyst systems Mn aminopyridine complex/H2O2/carboxylic acid in acetonitrile afford predominantly a mixture of the corresponding alcohol and the ester. The alcohol/ester ratio is higher for catalysts bearing electron-donating groups at the aminopyridine core. Isotopic labeling studies witness that the oxygen atom of the alcohol originates from the H2O2molecule, while the ester oxygen comes exclusively from the acid. Oxidation of ethylbenzene in the presence of acetic acid affords enantiomerically enriched 1-phenylethanol and 1-phenyl acetate, with close enantioselectivities and the same sign of absolute chirality. Experimental data and density functional theory calculations provide evidence in favor of the rate-limiting benzylic H atom abstraction by the high-spin (S = 1) [LMnV(O)OAc]2+active species followed by competitive OH/OC(O)R rebound. This mechanism has been unprecedented for Ca'H oxidations catalyzed by bioinspired Mn complexes. The trends governing the alcohol/ester ratios have been rationalized in terms of steric properties of the catalyst, acid, and substrate. copy; 2021 American Chemical Society.

Direct Nucleophilic Substitution of Alcohols Using an Immobilized Oxovanadium Catalyst

Direct nucleophilic substitution of alcohols with thiols or carbon nucleophiles was achieved using a mesoporous silica-supported oxovanadium catalyst (VMPS4). Benzyl and allyl alcohols were compatible in this reaction under mild conditions, affording the products in high yields. The VMPS4 catalyst showed excellent chemoselectivity toward alcohols in the presence of acid-labile functional groups, which is in contrast to that observed for the commonly used Lewis acid catalysts, which exhibit poor selectivity. The VMPS4 catalyst could be recycled by simple centrifugation, and the catalytic activity was maintained over seven cycles.

A one-pot two-step synthesis of tertiary alcohols combining the biocatalytic laccase/TEMPO oxidation system with organolithium reagents in aerobic aqueous media at room temperature

The one-pot/two-step combination of enzymes and polar organometallic chemistry in aqueous media is for the first time presented as a proof-of-concept study. The unprecedented combination of the catalytic oxidation of secondary alcohols by the system laccase/TEMPO with the ultrafast addition (3 s reaction time) of polar organometallic reagents (RLi/RMgX) to thein situformed ketones, run under air at room temperature, allows the straightforward and chemoselective synthesis of tertiary alcohols with broad substrate scope and excellent conversions (up to 96%).

Shuttle arylation by Rh(I) catalyzed reversible carbon–carbon bond activation of unstrained alcohols

The advent of transfer hydrogenation and borrowing hydrogen reactions paved the way to manipulate simple alcohols in previously unthinkable manners and circumvented the need for hydrogen gas. Analogously, transfer hydrocarbylation could greatly increase the versatility of tertiary alcohols. However, this reaction remains unexplored because of the challenges associated with the catalytic cleavage of unactivated C–C bonds. Herein, we report a rhodium(I)-catalyzed shuttle arylation cleaving the C(sp2)–C(sp3) bond in unstrained triaryl alcohols via a redox-neutral β-carbon elimination mechanism. A selective transfer hydrocarbylation of substituted (hetero)aryl groups from tertiary alcohols to ketones was realized, employing benign alcohols as latent C-nucleophiles. All preliminary mechanistic experiments support a reversible β-carbon elimination/migratory insertion mechanism. In a broader context, this novel reactivity offers a new platform for the manipulation of tertiary alcohols in catalysis.

Expeditious and practical synthesis of tertiary alcohols from esters enabled by highly polarized organometallic compounds under aerobic conditions in Deep Eutectic Solvents or bulk water

An efficient protocol was developed for the synthesis of tertiary alcohols via nucleophilic addition of organometallic compounds of s-block elements (Grignard and organolithium reagents) to esters performed in the biodegradable choline chloride/urea eutectic mixture or in water. This approach displays a broad substrate scope, with the addition reaction proceeding quickly (20 s reaction time) and cleanly, at ambient temperature and under air, straightforwardly furnishing the expected tertiary alcohols in yields of up to 98%. The practicability of the method is exemplified by the sustainable synthesis of some representative S-trityl-L-cysteine derivatives, which are a potent class of Eg5 inhibitors, also via telescoped one-pot processes.