1760-46-9

Basic information

• Product Name: (2,2-diphenylacetyl) 2,2-diphenylacetate
• Synonyms: (2,2-diphenylacetyl) 2,2-diphenylacetate;Diphenylacetic Anhydride;Benzeneacetic acid, a-phenyl-, anhydride
• CAS NO: 1760-46-9
• Molecular Formula: C₂₈H₂₂O₃
• Molecular Weight: 406.47
• Mol File: 1760-46-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 96.0 to 100.0 °C
• Boiling Point: 182°C/3mmHg(lit.)
• Flash Point: 268.4°C
• Appearance: /
• Density: 1.0946 (rough estimate)
• Vapor Pressure: 1.97E-12mmHg at 25°C
• Refractive Index: 1.5460 (estimate)
• Solubility: soluble in Toluene
• CAS DataBase Reference: (2,2-diphenylacetyl) 2,2-diphenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2,2-diphenylacetyl) 2,2-diphenylacetate(1760-46-9)
• EPA Substance Registry System: (2,2-diphenylacetyl) 2,2-diphenylacetate(1760-46-9)

Safety Data

• Hazardous Substances Data: 1760-46-9(Hazardous Substances Data)

Usage

Preparation

To a flask containing 50 gm (0.236 mole) of diphenylacetic acid is added 50 gm (0.49 mole) of acetic anhydride and the solution refluxed for 2 hr. The excess acetic anhydride is removed by distillation and the thick brown liquid residue is treated with ether to cause crystallization of the anhydride product. The crystals are filtered, washed with cold ether, and dried to afford 43-44 gm (90-92%), m.p. 98°C. The product can also be distilled at 182°C (3.0 mm Hg).

InChI:InChI=1/C28H22O3/c29-27(25(21-13-5-1-6-14-21)22-15-7-2-8-16-22)31-28(30)26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20,25-26H

Upstream product

• 1871-76-7 diphenylacetic acid chloride 
• 117-34-0 2,2-diphenylacetic acid 
• 108-24-7 acetic anhydride 
• 141-82-2 malonic acid 
• 525-06-4 diphenyl ketene 
• 601-75-2 ethylmalonic acid 
• 7647-01-0 hydrogenchloride 
• 71-43-2 benzene 
• 7732-18-5 water 
• 60-29-7 diethyl ether 
• 118601-60-8 pentane-2,2,4,4-tetracarboxylic acid 
• 2902-98-9 2-chloro-2,2-diphenylacetyl chloride 

Downstream Products

• 103006-43-5 α-benzoylbenzyldiphenylacetate 
• 132715-14-1 Diphenyl-acetic acid (7R,8aS)-2-benzyl-octahydro-pyrrolo[1,2-a]pyrazin-7-yl ester 
• 132715-15-2 Diphenyl-acetic acid (7R,8aS)-2-phenethyl-octahydro-pyrrolo[1,2-a]pyrazin-7-yl ester 
• 132715-04-9 Diphenyl-acetic acid (7R,8aS)-2-methyl-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-7-yl ester 
• 132715-05-0 Diphenyl-acetic acid (7R,8aS)-2-benzyl-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-7-yl ester 
• 132715-06-1 Diphenyl-acetic acid (7R,8aS)-1,4-dioxo-2-phenethyl-octahydro-pyrrolo[1,2-a]pyrazin-7-yl ester 
• 132715-13-0 Diphenyl-acetic acid (7R,8aS)-2-methyl-octahydro-pyrrolo[1,2-a]pyrazin-7-yl ester; hydrochloride 
• 78842-03-2 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N²-(diphenylacetyl)guanosine 
• 190968-16-2 N-[9-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-9H-purin-6-yl]-2,2-diphenyl-acetamide 
• 101-81-5 Diphenylmethane 
• 117-34-0 2,2-diphenylacetic acid 
• 632-51-9 1,1,2,2-tetraphenylethylene 
• 15719-64-9 methylammonium carbonate 
• 58241-13-7 4-methoxyphenyl diphenylacetate 

Relevant articles and documents

PPh3/Selectfluor-Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis

By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.

Facile and direct synthesis of symmetrical acid anhydrides using a newly prepared powerful and efficient mixed reagent

An efficient mixed reagent for direct synthesis of symmetrical carboxylic anhydrides from carboxylic acids has been prepared. Carboxylic acids are converted to anhydrides using triphenylphosphine/ trichloroisocyanuric acid under mild reaction conditions at room temperature. Short reaction time, excellent yields of products, low cost, availability of reagents, simple experimental procedure, and easy work-up of the products are the main advantages of the presented method.

Selective esterifications of alcohols and phenols through carbodiimide couplings

Esterification of carboxylic acids capable of forming ketene intermediates upon treatment with carbodiimides permits the selective acylation of alcohols in the presence of phenols lacking strong electron-withdrawing groups. The selectivity of acylations involving highly acidic phenols could be reversed through the addition of catalytic amount of acid. Esterification of other carboxylic acids was found to proceed through the formation of symmetric anhydrides and provide the opposite chemoselectivity. In both cases the relative acylation rates of substituted phenols are consistent with a reaction mechanism involving an attack of phenolate anions on electrophilic intermediates such as ketenes and symmetric anhydrides, with the carbodiimides serving both as an activating reagent and as a basic catalyst.