1883-32-5

Basic information

• Product Name: 2,2-DIPHENYLETHANOL
• Synonyms: 2,2-diphenyl-1-ethanol;Benzeneethanol, beta-phenyl-;2,2-DIPHENYLETHANOL;RARECHEM AL BD 0122;beta-phenylphenethyl alcohol;β-Phenylbenzeneethanol;2,2-Diphenylethanol,97%;2,2-Diphenylethyl alcohol
• CAS NO: 1883-32-5
• Molecular Formula: C₁₄H₁₄O
• Molecular Weight: 198.26
• EINECS: 217-543-6
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds;Building Blocks;C11 to C30+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 1883-32-5.mol
• Article Data: 78

Chemical Properties

• Melting Point: 53-56 °C(lit.)
• Boiling Point: 190-192 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White/Crystalline Powder
• Density: 1.079
• Vapor Pressure: 8.14E-05mmHg at 25°C
• Refractive Index: 1.5680 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.62±0.10(Predicted)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2,2-DIPHENYLETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIPHENYLETHANOL(1883-32-5)
• EPA Substance Registry System: 2,2-DIPHENYLETHANOL(1883-32-5)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1883-32-5(Hazardous Substances Data)

Usage

Description

2,2-Diphenylethanol is an organic compound that is known for its participation in the Meerwein-Ponndorf-Verley type reduction reaction of trans-stilbene oxide with boron triisopropoxide in tetrahydrofuran. It is characterized by its white powder form.

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 articles and documents

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.]

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.

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.