93-99-2

Usage

Uses

Used in Chemical Synthesis:
Phenyl benzoate is used as a key reagent in the synthesis of soluble polyimides using dianhydride/diamine derivatives. It plays a crucial role in the formation of these polymers, which have a wide range of applications in various industries due to their excellent thermal stability, mechanical properties, and chemical resistance.
Used in Pharmaceutical Industry:
Phenyl benzoate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its aromatic nature and ester functionality make it a versatile building block for the development of new drugs and drug candidates.
Used in Fragrance Industry:
Due to its pleasant aroma, phenyl benzoate is used as a fragrance ingredient in the perfumery and cosmetics industry. It can be used to create a wide range of scents and is often used in combination with other fragrance compounds to achieve desired olfactory effects.
Used in Plasticizers Industry:
Phenyl benzoate is used as a plasticizer in the production of certain types of plastics and resins. Its ability to increase the flexibility and workability of these materials makes it a valuable component in the formulation of various plastic products.
Used in Dyes and Pigments Industry:
Phenyl benzoate is used as a precursor in the synthesis of dyes and pigments. Its aromatic structure and reactivity make it suitable for the production of a variety of colored compounds used in various applications, such as textiles, paints, and inks.

Preparation

A glass tube was charged with benzoic anhydride (1.13 g, 5.00 mmol), diphenyl carbonate (1.07 g, 5.00 mmol), and either Ti(OBu)4 (0.020 g, 0.059 mmol) or Sn(OMe)2Bu2 (0.017 g, 0.059 mmol) as catalyst. The reaction mixture was heated at 300 ℃ for 30 min. After cooling to room temperature, the crude product obtained was dissolved in dichloromethane (10 mL) and the solution was filtered. The solvent was evaporated and the product obtained after column chromatography (silica gel; CH2Cl2/cyclohexane, 4:1) was recrystallized from petroleum ether; yield 95%.

Synthesis Reference(s)

Canadian Journal of Chemistry, 61, p. 86, 1983 DOI: 10.1139/v83-015Synthesis, p. 908, 1983 DOI: 10.1055/s-1983-30561Tetrahedron Letters, 41, p. 1343, 2000 DOI: 10.1016/S0040-4039(99)02289-3

Safety Profile

Moderately toxic by ingestion. When heated it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise the ester from EtOH using ca twice the volume needed for complete dissolution at 69o. [Beilstein 9 IV 303.]

InChI:InChI=1/C13H10O2/c14-13(11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H

Upstream product

• 102-09-0 bis(phenyl) carbonate 
• 119-61-9 benzophenone 
• 532-32-1 sodium benzoate 
• 115-86-6 phosphoric acid triphenyl ester 
• 7074-00-2 peroxybenzoic acid phenylisopropyl ester 
• 4578-66-9 o-benzoyloxybenzoic acid 
• 55-21-0 benzamide 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 108-95-2 phenol 
• 119-36-8 methyl salicylate 
• 60-29-7 diethyl ether 
• 4279-76-9 phenoxyacetylene 
• 925-90-6 ethylmagnesium bromide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 13053-82-2 N-(1,3-thiazol-2-yl)benzamide 
• 13053-89-9 N-(pyrimidin-2'-yl)benzamide 
• 20736-37-2 triphenyldiketone 
• 37529-67-2 N-(4-methylthiazol-2-yl)benzamide 
• 25491-42-3 ethyl 2,2-dimethyl-3-oxo-3-phenylpropionate 
• 3559-04-4 N-benzoyl-benzenesulfonamide 
• 4682-94-4 furan-2-yl(4-hydroxyphenyl)methanone 
• 33357-46-9 N-(quinolin-2-yl)benzamide 
• 2208-05-1 2-(dimethylamino)ethyl benzoate 
• 76-84-6 triphenylmethyl alcohol 
• 86123-17-3 Benzoesaeure-<2,2-diphenylethenylester> 
• 1696-17-9 N,N-diethylbenzamide 
• 54441-65-5 isopropyl 3-oxo-3-(phenyl)propanoate 
• 57365-25-0 1,2,2,5,5,6-hexaphenyl-hexane-1,6-dione 

Relevant academic research and scientific papers

Synthesis, Characterization and Biological Evaluation of Schiff Base Transition Metal Complexes Derived from 4-Nitrobenzene-1,2-diamine and 5-Chloroisatin

A series of transition metal complexes of the type [MLX2], where M = Mn(II), Fe(II), Co(II), Ni(II), X = Cl–/CH3COO– and L = Schiff base derived from 4-nitrobenzene-1,2-diamine and 5-chloroisatin have been synthesized and characterized by elemental analysis, molar conductance, IR, UV-visible, magnetic moments measurement, 1H & 13C NMR and mass spectral studies. On the basis of physico-chemical studies and spectral evaluation, an octahedral geometry have been proposed for all metal(II) complexes. The antimicrobial activity of ligand and its metal complexes have been additionally screened against bacteria and fungi. Metal(II) complexes show good activity as compared to ligand towards studied microorganisms and also metal complexes checked for their catalytic properties for benzoylation of phenol.

Highly efficient oxidation of diphenylmethane to benzophenone employing a novel ruthenium catalyst with tert-butylhydroperoxide under mild conditions

The ruthenium complex Ru(bpbp)(pydic) (bpbp = 2,6-bis(1-phenylbenzimidazol- 2-yl), pydic = pyridine-2,6-dicarboxy acid) has been synthesized and testedin the selective oxidation of diphenylmethane tobenzophe-none utilizing tert-butylhydroperoxide as the terminal oxidant. The influence of various reaction parameters such as temperature, catalyst amount and nature of solvent on the activity and selectivity was evaluated. Diphenylmethane was converted with 94% conversion and 100% selectivity to benzophenone under the optimized reaction conditions, inwhich the turnover number (TON) of catalyst reached 94,000. Moreover, a plausible reaction mechanism through redox ruthenium species was proposed.

Functional analysis of repositioned anilide derivatives as anticancer compounds

Off the different types cancers 40% of the population have been observed to be affected by leukemia. Contemporary therapeutics is focusing on generation of new synthetic analogues that can exert maximum positive physiological effect with minimum dosage and negligible deleterious side effects. New generation pharmacists are focusing on such promising effects of Imatinib (a potential anti-cancer drug molecule), Dasatinib, Pelitinib and Nilotinib. The present research study focuses on novel synthesized anilides derivative against BCR-ABL kinase as potential anti-leukemic agent. Validation of the compounds by molecular docking with specific BCR-ABL kinase confirmed their activity. Toxicity prediction of these compounds helped to identify sustainability as therapeutic molecules. The IC50 values were calculated (211 ug, 175 ug, 272ug for compounds A, B, C resp.) and the mode of cell death was gauged by DNA laddering assay. The cells were observed to be induced for programmed cell death. By validating and in-vivo testing of three synthesized compounds, the compound B was observed to be more stable thermodynamically with a potentially vital active site and appears to be a promising anti-leukemic factor. The present research thus lays a preliminary platform in world of pharmaceutics, where these new analogues appear to be efficient, target specific and less toxic molecules.

Mechanically induced solvent-free esterification method at room temperature

Herein, we describe two novel strategies for the synthesis of esters, as achieved under high-speed ball-milling (HSBM) conditions at room temperature. In the presence of I2 and KH2PO2, the reactions afford the desired esterification derivatives in 45% to 91% yields within 20 min of grinding. Meanwhile, using KI and P(OEt)3, esterification products can be obtained in 24% to 85% yields after 60 min of grinding. In addition, the I2/KH2PO2 protocol was successfully extended to the late-stage diversification of natural products showing the robustness of this useful approach. Further application of this method in the synthesis of inositol nicotinate was also discussed. This journal is

A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling reagents in conjunction with solvents with considerable issues such as dichloromethane (DCM) and N,N-dimethylformamide (DMF). To overcome these issues, we have developed a solvent-reagent selection guide for the formation of esters via Steglich-type reactions with the aim of providing safer, more sustainable conditions. Optimum reaction conditions have been identified after high-throughput screening of solvent-reagent combinations, namely the use of Mukaiyama's reagent (Muk) in conjunction with solvent dimethyl carbonate (DMC). The new reaction conditions were also exemplified through the synthesis of a small selection of building-block like molecules and includes the formation of t-butyl esters.

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Conversion of esters to thioesters under mild conditions

We report conversion of esters to thioestersviaselective C-O bond cleavage/weak C-S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad substrate scope and excellent functional group tolerance. The strategy was successfully deployed in late-stage thioesterification, site-selective cross-coupling/thioesterification/decarbonylation and easy-to-handle gram scale thioesterification. Selectivity and computational studies were performed to gain insight into the formation of weak C-S bonds by C-O bond cleavage, which contrasts with the traditional trend of nucleophilic additions to carboxylic acid derivatives.

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.