3524-62-7

Basic information

• Product Name: BENZOIN METHYL ETHER
• Synonyms: LABOTEST-BB LT00159464;BENZOIN METHYL ETHER;A-METHOXY-A-PHENYLACETOPHENONE;ALPHA-ETHOXY-ALPHA-PHENYLACETOPHENONE;ALPHA-METHOXY-ALPHA-PHENYLACETOPHENONE;2-METHOXY-2-PHENYLACETOPHENONE;2-METHOXY-1,2-DIPHENYLETHANONE;2-methoxy-1,2-diphenyl-ethanon
• CAS NO: 3524-62-7
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.27
• EINECS: 222-538-7
• Product Categories: Industrial/Fine Chemicals;Aromatic Acetophenones & Derivatives (substituted);Functional Materials;Photopolymerization Initiators;Building Blocks;C15 to C38;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 3524-62-7.mol

Chemical Properties

• Melting Point: 47-50 °C
• Boiling Point: 188-189 °C (15 mmHg)
• Flash Point: >230 °F
• Appearance: /powder
• Density: 1.128
• Vapor Pressure: 1.12E-06mmHg at 25°C
• Refractive Index: 1.6530 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in methanol.
• Merck: 14,1093
• BRN: 2052112
• CAS DataBase Reference: BENZOIN METHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOIN METHYL ETHER(3524-62-7)
• EPA Substance Registry System: BENZOIN METHYL ETHER(3524-62-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: AM9350000
• TSCA: Yes
• Hazardous Substances Data: 3524-62-7(Hazardous Substances Data)

Usage

Uses

Used in Coatings Industry:
Benzoin Methyl Ether is used as a solvent in UV curing inks, wood coatings, paper coatings, and other surface coatings for its ability to enhance the curing process and improve the overall performance of the coatings.
Used in Optical Fiber Industry:
In the optical fiber industry, Benzoin Methyl Ether is utilized as a curing agent for its effectiveness in promoting the rapid curing of materials, which is crucial for the manufacturing process of optical fibers.
Used in Electronics Industry:
Benzoin Methyl Ether is used in the electronics industry, specifically for PCB (Printed Circuit Board) manufacturing, as a solvent that aids in the proper functioning and performance of the boards.
Used in Screen Printing Industry:
In the screen printing industry, Benzoin Methyl Ether is employed as a solvent for its ability to improve the quality and durability of the printed materials.
Used in Paper Varnish Industry:
Benzoin Methyl Ether is used as a solvent in the paper varnish industry to enhance the curing process and improve the overall quality of the varnish.
Used in Powder Coatings Industry:
Benzoin Methyl Ether is utilized in the powder coatings industry as an anticratering agent, which helps to prevent the formation of craters and other surface defects in the final coated product.

InChI:InChI=1/C14H12O2.C2H6O/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12;1-3-2/h1-10,13,15H;1-2H3

Upstream product

• 13031-13-5 2-methoxy-2-phenylacetonitrile 
• 1889-85-6 benzoin dimethyl ketal 
• 105929-28-0 (R)-2-methoxy-2-phenylacetamide 
• 67-56-1 methanol 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 74-88-4 methyl iodide 
• 124-41-4 sodium methylate 
• 447-31-4 Desyl chloride 
• 1484-50-0 desyl bromide 
• 863-81-0 trans-2,5-dimethoxy-2,3,5,6-tetraphenyl-1,4-dioxane 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 89849-96-7 (Z)-1,2-diphenylvinylene 1,2-bis(trifluoromethanesulfonate) 
• 645-49-8 cis-stilben 
• 80-48-8 methyl p-toluene sulfonate 

Downstream Products

• 134-81-6 benzil 
• 50778-87-5 erythro-1,2-Diphenyl-2-methoxyethanol 
• 50778-88-6 threo-2-methoxy-1,2-diphenylethanol 
• 62398-10-1 2-acetoxy-2-phenylacetophenone 
• 78522-85-7 (RS,RS)-2-methoxy-1-(4-methoxy-phenyl)-1,2-diphenyl-ethanol 
• 93-58-3 benzoic acid methyl ester 
• 65-85-0 benzoic acid 
• 67-72-1 hexachloroethane 
• 27904-70-7 1-methoxy-1-phenyl-2,2,2-trichloroethane 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 3962-43-4 1,2-diphenyl-1,2-dimethoxy ethane, meso 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 108574-42-1 methoxy-1 phenyl-1 trimethylsiloxy-2 styrene 

Relevant articles and documents

Iridium-Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic α-Alkoxy Ketones

The asymmetric alkylation of acyclic ketones is a longstanding challenge in organic synthesis. Reported herein are diastereoselective and enantioselective allylic substitutions with acyclic α-alkoxy ketones catalyzed by a metallacyclic iridium complex to form products with contiguous stereogenic centers derived from the nucleophile and electrophile. These reactions occur between allyl methyl carbonates and unstabilized copper(I) enolates generated in situ from acyclic α-alkoxy ketones. The resulting products can be readily converted into enantioenriched tertiary alcohols and tetrahydrofuran derivatives without erosion of enantiomeric purity.

Vanadium Aminophenolate Complexes and Their Catalytic Activity in Aerobic and H2O2-Mediated Oxidation Reactions

Vanadium compounds supported by tetradentate amino-bis(phenolate) ligands, [VO(OMe)(O2NOBuMeMeth)] (1), [VO(OMe)(ON2OBuMe)] (2), [VO(OMe)(O2NNBuBuPy)] (3), and [VO(OMe)(O2NOBuBuFurf)] (4) [where (O2NOBuMeMeth) = MeOCH2CH2N(CH2ArOH)2, Ar = 3,5-C6H2-Me, tBu; (ON2OBuMe) = HOArCH2NMeCH2CH2NMeCH2ArOH, Ar = 3,5-C6H2-Me, tBu; (O2NNBuBuPy) = C5H4NCH2N(CH2ArOH)2, Ar = 3,5-C6H2-tBu2; (O2NOBuBuFurf) = C4H3OCH2N(CH2ArOH)2, Ar = 3,5-C6H2-tBu2] were synthesized and characterized by NMR spectroscopy, MALDI-TOF mass spectrometry and UV/Vis data. The catalytic activity of 1–4 as homogeneous catalysts in the aerobic oxidation of 4-methoxybenzyl alcohol and 1,2-diphenyl-2-methoxyethanol was explored. 1 and 2 showed moderately superior activity compared with 3 and 4, which might be due to increased stability of these complexes. 1–4 showed limited reactivity in H2O2-mediated oxidation of diphenyl ether and benzyl phenyl ether.

Sodium iodide-catalyzed direct α-alkoxylation of ketones with alcohols via oxidation of α-iodo ketone intermediates

The direct α-alkoxylation of ketones with alcohols via a sodium iodide-catalyzed oxidative cross-coupling has been developed. This protocol enables a range of alkyl aryl ketones to cross couple with an array of alcohols in synthetically useful yields. The mechanistic studies provided solid evidence supporting that an α-iodo ketone was a key reaction intermediate, being converted into an α-alkoxylated ketone via further oxidation to a hypervalent iodine species rather than a common nucleophilic substitution, and was generated from the ketone starting material via a radical intermediate. These new mechanism insights should have an effect on the design of iodide-catalyzed oxidative cross-coupling reactions between nucleophiles.

Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process

The α-arylation of enolizable aryl ketones can be carried out with aryl halides under transition-metal-free conditions using KOtBu in DMF. The α-aryl ketones thus obtained can be used for step- and cost-economic syntheses of fused heterocycles and Tamoxifen. Mechanistic studies demonstrate the synergetic role of base and solvent for the initiation of the radical process.

Oxidation of alcohols and activated alkanes with lewis acid-activated tempo

The reactivity of MCl3(η1O) (M = Fe, 1; Al, 2; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) with a variety of alcohols, including 3,4-dimethoxybenzyl alcohol, 1-phenyl-2-phenoxyethanol, and 1,2-diphenyl-2-methoxyethanol, was investigated using NMR spectroscopy and mass spectrometry. Complex 1 was effective in cleanly converting these substrates to the corresponding aldehyde or ketone. Complex 2 was also able to oxidize these substrates; however, in a few instances the products of overoxidation were also observed. Oxidation of activated alkanes, such as xanthene, by 1 or 2 suggests that the reactions proceed via an initial 1-electron concerted proton-electron transfer (CPET) event. Finally, reaction of TEMPO with FeBr3 in Et2O results in the formation of a mixture of FeBr3(η1OH) (23) and [FeBr2(η1OH)]2(μ-O) (24), via oxidation of the solvent, Et2O.

SELECTIVE AEROBIC ALCOHOL OXIDATION METHOD FOR CONVERSION OF LIGNIN INTO SIMPLE AROMATIC COMPOUNDS

Described is a method to oxidize lignin or lignin sub-units. The method includes oxidation of secondary benzylic alcohol in the lignin or lignin sub-unit to a corresponding ketone in the presence of unprotected primarily aliphatic alcohol in the lignin or lignin sub-unit. The optimal catalyst system consists of HNO3 in combination with another Br?nsted acid, in the absence of a metal-containing catalyst, thereby yielding a selectively oxidized lignin or lignin sub-unit. The method may be carried out in the presence or absence of additional reagents including TEMPO and TEMPO derivatives.

Chemoselective metal-free aerobic alcohol oxidation in lignin

An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.

Synthesis, structure and oxidation of alkynes using a μ-oxo diiron complex with the ligand bis (1-(pyridin-2-ylmethyl)-benzimidazol-2-yl methyl) ether

New ligand bis (1-(pyridin-2-ylmethyl)-benzimidazol-2-ylmethyl ether and its μ-oxo diferric complex has been synthesized and characterized. The dimeric [LClFe-O-FeCl3] has been characterized crystallographically, and shows that iron atoms occupy inequivalent coordination sites. One of the Fe (III) atom is coordinated by two benzimidazole nitrogens, one ether oxygen and bridging oxide oxygen, forming the equatorial plane while one Cl- ion and the oxygen atom of a DMF molecule occupy the axial fifth and the sixth coordination positions. The second Fe (III) is tetrahedrally coordinated by three Cl- ions and the bridging oxide oxygen O. The bridging oxide anion is unsymmerically coordinated to the two Iron (III) atoms. Oxidation of aromatic alkynes was investigated using this complex as catalyst with small amount of tert-butyl hydroperoxide (TBHP) and Hydrogen peroxide (H 2O2) as an alternate source of oxygen. Isolated products were characterized by GC-Mass. Solvent, temperature, Stoichiometry and oxidant variation are studied and reaction conditions have been optimized. Dicarbonyl and α,β-acetylenic ketone are the major product and depend on the nature of the alkyne employed.

Oxidative iodination of carbonyl compounds using ammonium iodide and oxone

A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones reacted smoothly yielding a mixture of 1-iodo and 3-iodo ketones with the predominant formation of 1-iodoproduct.

Visible light flavin photo-oxidation of methylbenzenes, styrenes and phenylacetic acids

We report the photocatalytic oxidation of benzylic carbon atoms under mild conditions using riboflavin tetraacetate as photocatalyst and blue-emitting LEDs (440 nm) as light source. Oxygen is the terminal oxidant and hydrogen peroxide appears as the only byproduct in most cases. The process oxidizes toluene derivatives, stilbenes, styrenes and phenylacetic acids to their corresponding benzaldehydes. A benzyl methyl ether and acylated benzyl amines are oxidized directly to the corresponding methyl ester or benzylimides. The mechanism of the reactions has been investigated and the results indicate that oxygen addition to benzyl radicals is a key step of the oxidation process in the case of phenylacetic acids.