1883-32-5

Usage

Uses

Used in Chemical Synthesis:
2,2-Diphenylethanol is used as a reagent in the chemical synthesis process for its ability to participate in Meerwein-Ponndorf-Verley type reduction reactions. This application is significant for the production of various chemical compounds and intermediates.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2-Diphenylethanol is used as a building block for the synthesis of various pharmaceutical compounds. Its chemical properties make it a valuable component in the development of new drugs and medications.
Used in Research and Development:
2,2-Diphenylethanol is also utilized in research and development settings, where its unique chemical properties are explored for potential applications in creating new materials, improving existing synthesis methods, and understanding the underlying chemistry of various reactions.
Used in Cosmetics Industry:
In the cosmetics industry, 2,2-Diphenylethanol may be used as an ingredient in the formulation of various cosmetic products due to its white powder form and chemical stability. It can contribute to the texture, consistency, or other properties of the final product.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 5694, 1956 DOI: 10.1021/ja01602a063The Journal of Organic Chemistry, 26, p. 4199, 1961 DOI: 10.1021/jo01069a005

InChI:InChI=1/C14H14O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14-15H,11H2

Upstream product

• 96-09-3 styrene oxide 
• 60-29-7 diethyl ether 
• 530-48-3 1,1-Diphenylethylene 
• 50-00-0 formaldehyd 
• 5152-68-1 benzhydryl sodium 
• 1871-76-7 diphenylacetic acid chloride 
• 677-22-5 tert-butylmagnesium chloride 
• 882-59-7 1,1-diphenyloxirane 
• 947-91-1 Diphenylacetaldehyde 
• 4695-13-0 2,2-diphenylacetamide 
• 3468-99-3 ethyl diphenylacetate 
• 117-34-0 2,2-diphenylacetic acid 
• 37537-23-8 (phenyl)methyl 2,2-diphenylacetate 
• 108-86-1 bromobenzene 

Downstream Products

• 115210-31-6 tetra-N-ethyl-2-(2,2-diphenyl-ethoxy)-propanediyldiamine 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 5216-46-6 1,1-diphenyl-2-chloroethane 
• 612-00-0 1,1'-ethylidenebis-benzene 
• 111583-55-2 2,2-diphenylethyl benzoate 
• 7512-05-2 oxalic acid bis-(2,2-diphenyl-ethyl ester) 
• 6319-82-0 ethyl 2,2-diphenylacetate 
• 15518-86-2 [2-(2,2-diphenyl-ethoxy)-ethyl]-dimethyl-amine 
• 6944-27-0 2,2-diphenylethyl 4-methylbenzenesulfonate 
• 7475-76-5 3,5-dinitro-benzoic acid-(2,2-diphenyl-ethyl ester) 
• 55505-08-3 (2,2-Diphenyl-ethoxysulfonyl)-phenyl-acetic acid 
• 530-48-3 1,1-Diphenylethylene 
• 71351-02-5 1,1-diphenylethanethiol 
• 106881-53-2 Sulfamic acid 2,2-diphenyl-ethyl ester 

Relevant academic research and scientific papers

A practical decarboxylative hydroxylation of carboxylic acids

Irradiation of esters of N-hydroxy-2-thiazolinethione under air or oxygen at room temperature in the presence of tert-dodecanethiol affords the corresponding nor-alcohols after a reductive work-up.

Method for activation and recycling of trityl resins

This note describes a rapid and mild strategy for the loading of alcohols and anilines onto a polystyrene triphenylmethyl (trityl) resin. High loadings were obtained in a matter of minutes by treating resin-bound trityl chloride with triethyloxonium tetrafluoroborate followed by alcohols or anilines. Yields were comparable or better than known literature methods. Recycling of the recovered resin was also possible using the developed method.

Reduction of carbonyl compounds via hydrosilylation catalyzed by well-defined PNP-Mn(I) hydride complexes

Reduction reactions of unsaturated compounds are fundamental transformations in synthetic chemistry. In this context, the reduction of polarized double bonds such as carbonyl or C=C motifs can be achieved by hydrogenation reactions. We describe here a highly chemoselective Mn(I)-based PNP pincer catalyst for the hydrosilylation of aldehydes and ketones employing polymethylhydrosiloxane (PMHS) as inexpensive hydrogen donor. Graphic abstract: [Figure not available: see fulltext.]

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides

The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Uranyl(VI) Triflate as Catalyst for the Meerwein-Ponndorf-Verley Reaction

Catalytic transformation of oxygenated compounds is challenging in f-element chemistry due to the high oxophilicity of the f-block metals. We report here the first Meerwein-Ponndorf-Verley (MPV) reduction of carbonyl substrates with uranium-based catalysts, in particular from a series of uranyl(VI) compounds where [UO2(OTf)2] (1) displays the greatest efficiency (OTf = trifluoromethanesulfonate). [UO2(OTf)2] reduces a series of aromatic and aliphatic aldehydes and ketones into their corresponding alcohols with moderate to excellent yields, using iPrOH as a solvent and a reductant. The reaction proceeds under mild conditions (80 °C) with an optimized catalytic charge of 2.3 mol % and KOiPr as a cocatalyst. The reduction of aldehydes (1-10 h) is faster than that of ketones (>15 h). NMR investigations clearly evidence the formation of hemiacetal intermediates with aldehydes, while they are not formed with ketones.

Catalytic C-C coupling of diazo compounds with arylboronic acids: Using surface modified sewage sludge as catalyst

A green, mild and efficient synthesis of diarylmethines using sewage sludge-derived carbonaceous materials (SW) by perchloric acid catalyzed coupling reactions between diazo compounds and arylboronic acids was developed. The reaction shows a high level of functional tolerance and a broad substrate scope. Furthermore, the highly selective 1,2-alkyl shift products were furnished through the sterically demanding R4, R5 migration of diazo compounds (3-diazochromanone). The structures of 1,2-shift products have been further confirmed by single-crystal X-ray analysis. Significantly, the synthesis of the core structures of darifenacin (a clinical drug for overactive bladder syndrome, OAB) and diclofensine (a stimulant drug showing antidepressant and monoamine reuptake inhibitor activity) further demonstrated the efficacy and synthetic potential of this method. This journal is

Continuous-Flow Amide and Ester Reductions Using Neat Borane Dimethylsulfide Complex

Reductions of amides and esters are of critical importance in synthetic chemistry, and there are numerous protocols for executing these transformations employing traditional batch conditions. Notably, strategies based on flow chemistry, especially for amide reductions, are much less explored. Herein, a simple process was developed in which neat borane dimethylsulfide complex (BH3?DMS) was used to reduce various esters and amides under continuous-flow conditions. Taking advantage of the solvent-free nature of the commercially available borane reagent, high substrate concentrations were realized, allowing outstanding productivity and a significant reduction in E-factors. In addition, with carefully optimized short residence times, the corresponding alcohols and amines were obtained in high selectivity and high yields. The synthetic utility of the inexpensive and easily implemented flow protocol was further corroborated by multigram-scale syntheses of pharmaceutically relevant products. Owing to its beneficial features, including low solvent and reducing agent consumption, high selectivity, simplicity, and inherent scalability, the present process demonstrates fewer environmental concerns than most typical batch reductions using metal hydrides as reducing agents.

Method for preparation of aromatic alcohol by photocatalysis of aromatic aldehyde conversion

The invention relates to a method for preparation of aromatic alcohol by photocatalysis of aromatic aldehyde conversion. By means of a photocatalyst, under the conditions of illumination and inert gas, fatty alcohol is adopted as a proton donor for reduction reaction on aromatic aldehyde to obtain corresponding aromatic alcohol. Fatty alcohol is used as the proton donor, and light energy is used as the energy source to promote high-conversion-rate and high-selectivity synthesis of a series of aromatic alcohol compounds from aromatic aldehyde, the method has universal applicability, and is expected to realize industrial production; and the reaction process is green and environment-friendly, low in cost, easy to operate, short in reaction period, high in conversion rate and good in selectivity.

Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation

A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.