76-89-1

Basic information

• Product Name: Methyl benzilate
• Synonyms: alpha-hydroxy-alpha-phenyl-benzeneaceticacimethylester;alpha-Hydroxydiphenylacetic acid, methyl ester;Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, methyl ester;ethyl 2-hydroxy-2,2-diphenylacetate;ethyl a-hydroxydiphenylacetate;ethyl a-phenylmandelate;ethyl hydroxydiphenylacetate;Methyl benzillate
• CAS NO: 76-89-1
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27
• EINECS: 200-991-1
• Product Categories: Aromatic Esters
• Mol File: 76-89-1.mol

Chemical Properties

• Melting Point: 73 °C
• Boiling Point: 187 °C
• Flash Point: 187°C/13mm
• Appearance: white crystalline powder
• Density: 1.1515 (rough estimate)
• Vapor Pressure: 0.000134mmHg at 25°C
• Refractive Index: 1.5570 (estimate)
• PKA: 11.38±0.29(Predicted)
• Water Solubility: Soluble in methanol. Insoluble in water.
• Merck: 14,1080
• BRN: 2121492
• CAS DataBase Reference: Methyl benzilate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl benzilate(76-89-1)
• EPA Substance Registry System: Methyl benzilate(76-89-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• TSCA: Yes
• Hazardous Substances Data: 76-89-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl benzilate is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its chemical properties make it a suitable candidate for use in the development of new pharmaceutical compounds.
Used in Flavor and Fragrance Industry:
Due to its pleasant odor, methyl benzilate is also used in the flavor and fragrance industry. It is an important component in the creation of various scents and flavors, adding a unique and desirable aroma to products.
Used in Chemical Synthesis:
Methyl benzilate is utilized in chemical synthesis processes, particularly in the production of other organic compounds. Its reactivity and stability make it a valuable building block for the creation of a wide range of chemicals.
Used in Solvent Applications:
As a solvent, methyl benzilate is employed in various industrial processes. Its ability to dissolve a wide range of substances makes it a versatile and useful component in the production of various products.

InChI:InChI=1/C15H14O3/c1-18-14(16)15(17,12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11,17H,1H3

Upstream product

• 67-56-1 methanol 
• 51552-62-6 methoxy-diphenyl-acetic acid methyl ester 
• 57272-44-3 methyl α-hydroperoxy-α,α-diphenylacetate 
• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 31469-19-9 diphenyl-2,2 methoxy-1 trimethylsiloxy-1 ethylene 
• 3469-00-9 methyl 2,2-diphenylacetate 
• 76-93-7 Benzilic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 22979-35-7 Methyl phenyldiazoacetate 
• 1634-04-4 tert-butyl methyl ether 
• 134-81-6 benzil 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 119-61-9 benzophenone 
• 74-88-4 methyl iodide 

Downstream Products

• 4746-88-7 2-hydroxy-2,2-diphenyl-N-(2-piperidin-1-yl-ethyl)-acetamide 
• 28789-59-5 benzilic acid-(1-ethyl-[4]piperidyl ester) 
• 16444-19-2 2-hydroxy-2,2-diphenylacetic acid 3α-(8-azabicyclo(3,2,1))-3-octyl ester 
• 101594-90-5 methyl 2-ethoxy-2,2-diphenylacetate 
• 57258-61-4 piperidin-3-yl 2-hydroxy-2,2-diphenylacetate 
• 315680-06-9 (R)-1-methylpiperidin-3-yl 2-hydroxy-2,2-diphenylacetate 
• 57295-18-8 hydroxy-diphenyl-acetic acid 1-methyl-piperidin-4-ylmethyl ester 
• 102156-75-2 benzilic acid-((S)-1-methyl-pyrrolidin-2-ylmethyl ester) 
• 74040-58-7 Benzilsaeure- 
• 5746-42-9 Benzilylcholine mustard 
• 857619-09-1 5,5-diphenyl-furan-2,4-dione 

Relevant articles and documents

A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands

A general procedure for the asymmetric synthesis of highly substituted 1,2-amino alcohols in high yield and diastereoselectivity is described that uses organometallic additions of a wide range of nucleophiles to tert-butylsulfinimines as the key step. The addition of organolithium reagents to these imines follows a modified Davis model. The diastereoselectivity for this reaction depends significantly on both the nucleophile and electrophile. These highly substituted 1,2-amino alcohols are used to synthesize stereochemically diverse and structurally novel, polysubstituted 2,2′-methylene(bisoxazoline) ligands in high yields.

1,5,7-Triazabicyclo[4.4.0]dec-5-ene Enhances Activity of Peroxide Intermediates in Phosphine-Free α-Hydroxylation of Ketones

The critical role of double hydrogen bonds was addressed for the aerobic α-hydroxylation of ketones catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), in the absence of either a metal catalyst or phosphine reductant. Experimental and theoretical investigations were performed to study the mechanism. In addition to initiating the reaction by proton abstraction, a more important role of TBD was revealed, that is, to enhance the oxidizing ability of peroxide intermediates, allowing DMSO to be used rather than commonly used phosphine reductants. Further characterizations with nuclear Overhauser effect spectroscopy (NOESY) confirmed the presence of double hydrogen bonds between TBD and the ketone, and kinetic studies suggested the attack of dioxygen on the TBD-enol adduct to be the rate-determining step. This work should encourage the application of TBD as a catalyst for oxidations.

Time-Economical Synthesis of Diarylacetates Enabled by TfOH-Catalyzed Arylation of α-Aryl-α-Diazoesters with Arenes

Diarylacetates are privileged structures of many bioactive natural products and pharmaceutical compounds. A time-economical synthesis of diarylacetates by TfOH-catalyzed arylation of α-aryl-α-diazoesters with arenes is described. This protocol provides a variety of diarylacetates in good yields with broad substrate scope, excellent functional group compatibility, and mild reaction conditions. Also, a new mechanism for the arylation reaction of α-aryl-α-diazoesters with arenes under TfOH catalysis is presented.

Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation

A visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates. Alternatively, photochemical reactions show a broad scope, can be performed under air and tolerate a wide variety of functional groups. Reaction-evolution monitoring, DFT calculations and control experiments have been used to evaluate the main aspects of this intricate mechanistic scenario. Biologically active molecules Adiphenine, Benactyzine and Aprophen have been prepared as examples of synthetic applications.

A 2 the hydroxy [...] ― 2,2 the the ― 3 α [...] diphenylgermanium acetic acid [...] (8 the [...] azabicyclo [3, 2, 1]) ― 3 the method for the preparation of octyl [...]

The invention discloses a method for preparing 2-hydroxy-2,2-diphenylacetic acid-3alpha-(8-aza-bicyclo(3,2,1))-3-trioctyl. The method comprises the following steps of: by taking dibenzoyl as a raw material, carrying out rearrangement on the raw material so as to obtain dihydroxy-phenylacetic acid; reacting dihydroxy-phenylacetic acid with dimethyl carbonate under the DBU catalysis and microwave actions so as to obtain methyl benzilate; reacting the methyl benzilate with tropine so as to obtain tropine benzilate; and carrying out N formylation and alcoholysis on the obtained tropine benzilate so as to obtain nor-tropine benzilate. Compared with the prior art, the total reaction time of the method disclosed by the invention is greatly reduced, the total yield is increased greatly, and the reaction condition is more simple, and therefore, the method is suitable for industrial production.

One-pot esterification and amide formation via acid-catalyzed dehydration and ritter reactions

Esterification of carboxylic acid is achieved using acetonitrile as a water trap. Water liberated during esterification is consumed in cyanide hydrolysis, thereby driving the esterification to completion. Substrates having carboxylic acid and nitrile groups undergo intramolecular dehydration and rehydration to amido esters in the absence of acetonitrile. Cyano acids also undergo esterification and Ritter reaction in one pot when excess alcohol is used. For the first time, we have observed an interesting Ritter reaction of primary alcohols, leading to ester amide product in one pot. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Highly efficient C-H hydroxylation of carbonyl compounds with oxygen under mild conditions

A transition-metal-free Cs2CO3-catalyzed α-hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α-hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very environmentally friendly and practical. This transformation is highly efficient and highly selective for tertiary C(sp3)-H bond cleavage. OH, so simple! A transition-metal-free Cs2CO 3-catalyzed α-hydroxylation of carbonyl compounds with O 2 provided a variety of tertiary α-hydroxycarbonyl compounds (see scheme; DMSO=dimethyl sulfoxide), which are widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very efficient and practical.

One-pot esterification and Ritter reaction: Chemo- and regioselectivity from tert-butyl methyl ether

tert-Butyl methyl ether (TBME) has been effectively used as a reagent for esterification of carboxylic acids. By varying amounts of sulfuric acid, a remarkable regioselectivity in esterification has been demonstrated. Additionally, under the present reaction conditions, one-pot esterification and Ritter reaction are achieved in almost quantitative yield.

A dinuclear palladium catalyst for α-Hydroxylation of carbonyls with O2

A chemo- and regioselective α-hydroxylation reaction of carbonyl compounds with molecular oxygen as oxidant is reported. The hydroxylation reaction is catalyzed by a dinuclear Pd(II) complex, which functions as an oxygen transfer catalyst, reminiscent of an oxygenase. The development of this oxidation reaction was inspired by discovery and mechanism evaluation of previously unknown Pd(III)-Pd(III) complexes.

Electroreductive acylation of aromatic ketones with acylimidazoles

The intermolecular reductive coupling of aromatic ketones with acylimidazoles was effected by electroreduction in the presence of chlorotrimethylsilane and gave α-trimethylsiloxy ketones and esters. The best result was obtained using Bu4NPF6 as a supporting electrolyte and a Pb cathode in THF. The α-trimethylsiloxy-containing products were transformed to the corresponding α-hydroxy ketones and esters by treatment with TBAF in THF. This method was also effective for the intramolecular reductive coupling of δ- and ε-keto acylimidazoles.