10166-08-2

Usage

Uses

Used in Flavor and Fragrance Industry:
Benzeneacetaldehyde, 2-methyl(9CI) is used as a flavoring agent in food and beverages, imparting a distinctive aroma and enhancing the overall taste experience. Its pleasant odor also makes it a valuable ingredient in perfumes and cosmetics, contributing to the creation of various scents and fragrances.
Used in Chemical Production:
Benzeneacetaldehyde, 2-methyl(9CI) is utilized in the production of other chemicals, including pharmaceuticals, dyes, and pesticides. Its versatile chemical properties allow it to serve as an intermediate in the synthesis of a wide range of products, making it an essential component in various chemical manufacturing processes.
Safety Precautions:

InChI:InChI=1/C9H10O/c1-8-4-2-3-5-9(8)6-7-10/h2-5,7H,6H2,1H3

Upstream product

• 4819-77-6 1,1,2-triethoxyethane 
• 19819-98-8 2-o-tolylethanol 
• 4254-29-9 indan-2-ol 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 861353-04-0 4-methyl-3-phenyl-benzo[h]chromen-2-one 
• 4217-66-7 1,2-dihydroxy-2-phenylpropane 
• 7732-18-5 water 
• 144-62-7 oxalic acid 
• 7664-93-9 sulfuric acid 
• 860753-31-7 1,2-diethoxy-1-o-tolyl-ethane 
• 644-36-0 o-methylphenylacetic acid 
• 2783-26-8 o-methylstyrene oxide 
• 529-20-4 2-methylphenyl aldehyde 
• 40851-62-5 methyl o-tolylacetate 

Downstream Products

• 433230-12-7 {3-[(4R,5S)-2-Acetoxy-4-hydroxy-5-((E)-(S)-3-hydroxy-4-o-tolyl-but-1-enyl)-cyclopent-1-enylsulfanyl]-propylsulfanyl}-acetic acid methyl ester 
• 862205-49-0 [4-methyl-2-oxo-1-(2-o-tolyl-ethylamino)-1,2-dihydropyridin-3-yl]acetic acid methyl ester 
• 1321200-17-2 (E)-3-methyl-3-(2-methylstyryl)dihydrofuran-2(3H)-one 
• 1321200-22-9 3-methyl-3-(2-(o-tolyl)-2-(triethylsilylperoxy)ethyl)dihydrofuran-2(3H)-one 
• 1321200-12-7 3-(1-hydroxy-2-(o-tolyl)ethyl)-3-methyldihydrofuran-2(3H)-one 
• 1352708-05-4 N-(4-cyanophenyl)-2-oxo-2-(o-tolyl)acetamide 
• 1374667-35-2 2-oxo-2-(o-tolyl)-N,N'-di(p-tolyl)acetimidamide 
• 105702-07-6 2-(2-methylphenyl)quinoxaline 
• 1398057-52-7 2-phenyl-4-(o-tolyl)-1H-pyrrole 
• 1398057-93-6 3-phenyl-4-o-tolyl-1H-pyrrole 
• 1431696-12-6 (E)-1-methyl-2-(3-(phenylsulfonyl)allyl)benzene 
• 1431696-18-2 (E)-1-methyl-2-(3-(phenylsulfonyl)prop-1-en-1-yl)benzene 
• 1197985-25-3 3,5-di(o-tolyl)pyridine 

Relevant academic research and scientific papers

Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants

Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.

Regioselective, Diastereoselective, and Enantioselective One-Pot Tandem Reaction Based on an in Situ Formed Reductant: Preparation of 2,3-Disubstituted 1,5-Benzodiazepine

The 1,5-benzodiazepines are important skeletons frequently contained in medicinal chemistry. Herein, we described an unexpected tandem cyclization/transfer hydrogenation reaction for obtaining chiral 2,3-disubstituted 1,5-benzodiazepines. The enolizable aryl aldehydes were chosen as substrates to react with symmetric and unsymmetric o-phenylenediamines. The unforeseen tandem reaction occurred among many possible latent side reactions under chiral phosphoric acid catalysis and affords the corresponding products in moderate yields and regioselectivities, good diastereoselectivities, and enantiomeric ratio (up to 99:1).

Tetradentate amido azo Schiff base Cu(II), Ni(II) and Pd(II) complexes: Synthesis, characterization, spectral properties, and applications to catalysis in C–C coupling and oxidation reaction

New Schiff base ligands (H2L1 & H2L2) were synthesized by the reaction of salicylaldehyde with (2-((2-aminophenyl)diazenyl)-N-alkylaniline), and were used for the preparation of complexes with Cu(II), Ni(II) and Pd(II) metal ions. The structural features of the synthesized compounds were examined by UV–Vis, IR and 1H NMR spectroscopy. The crystal structures of Schiff base (H2L1) and two metal complexes Cu(L1) and Ni(L2) were determined by single crystal X-ray diffraction. The studies revealed that the synthesized Schiff bases existed as tetradentate (N,N,N,O) ligands and bonded to the metal ions through the donor atoms of the amido nitrogen, azo nitrogen, azomethine nitrogen and phenolic oxygen atoms. The redox property of Cu(L1) and Ni(L1) and emission behavior of ligand H2L1 and complexes Cu(L1) and Ni(L1) were examined. The complex Cu(L1) shows excellent catalytic activity towards oxidation of benzyl alcohol to benzyldehyde (under solvent-free condition) using H2O2 as the oxidant. Complex Pd(L1) acts as highly efficient catalyst in the Suzuki–Miyaura cross-coupling reaction of various aryl halides with phenyl boronic acid to produce the corresponding biaryls with high yields under mild reaction conditions. Both the catalysts Cu(L1) and Pd(L1) were easily recovered by simple chromatographic separation and reused for next catalytic cycle.

Ring Expansion of Epoxides under Br?nsted Base Catalysis: Formal [3+2] Cycloaddition of β,γ-Epoxy Esters with Imines Providing 2,4,5-Trisubstituted 1,3-Oxazolidines

A novel ring-expansion reaction of epoxides under Br?nsted base catalysis was developed. The formal [3+2] cycloaddition reaction of β,γ-epoxy esters with imines proceeds in the presence of triazabicyclodecene (TBD) as a superior Br?nsted base catalyst to afford 2,4,5-trisubstituted 1,3-oxazolidines in a highly diastereoselective manner. This reaction involves the ring opening of the epoxides with the aid of the Br?nsted base catalyst to generate α,β-unsaturated esters having an alkoxide at the allylic position, which would formally serve as a synthetic equivalent of the 1,3-dipole, followed by a cycloaddition reaction with imines in a stepwise fashion. This methodology enables the facile synthesis of enantioenriched 1,3-oxazolidines from easily accessible enantioenriched epoxides.

Design and biological evaluation of phenyl-substituted analogs of β-phenylethylidenehydrazine

β-Phenylethylidenehydrazine (PEH) has been demonstrated previously to be an inhibitor of γ-aminobutyric acid transaminase (GABA-T) and to cause a marked increase in rat brain levels of GABA, a major neurotransmitter. A group of PEH analogs, possessing a variety of substituents (Me, OMe, Cl, F, and CF3) at the 2-, 3-, and 4-positions of the phenyl ring, were synthesized for evaluation as inhibitors of GABA-T. The details of the synthesis and chemical characterization of the analogs are described. Preliminary in vitro screening for GABA-T inhibition showed that all the analogs possessed activity against this enzyme, although substitution of CF3 at the 2- and 4-positions caused reduced activity. One of the drugs, 4-fluoro-β- phenylethylidenehydrazine, was investigated further ex vivo, where it was shown to inhibit GABA-T, elevate brain levels of GABA, and decrease levels of glutamine, similar to the profile observed previously for PEH.

Selective switchable iron-catalyzed hydrosilylation of carboxylic acids

Selective reduction of carboxylic acids either to aldehydes or alcohols is achieved using a one pot procedure based on iron-catalyzed hydrosilylations. Using phenylsilane and (COD)Fe(CO)3 catalyst under UV-irradiation at rt, alcohols were obtained specifically in good yields, whereas aldehydes were selectively obtained using TMDS and (t-PBO)Fe(CO)3 catalyst under thermal activation.

Synthesis method of phenylacetaldehyde derivative

The present invention discloses a synthesis method of phenylacetaldehyde derivative, a benzaldehyde derivative is adopted as a raw material, an intermediate 2-methoxyvinylphenyl derivative is obtained through synthesis, then the phenylacetaldehyde derivative is obtained through synthesis, and the substituent group R of the benzaldehyde derivative includes but is not limited to m-methyl, m-ethyl, m-nitrile group, p-methyl, o-methyl, o-nitro and 2, 6-dimethyl. The synthesis process is simple, synthesis conditions are mild, post-treatment is relatively simple, and industrial production is easy; the universality is good, and substrates with different functional groups are compatible; the yield is considerable, part of compounds are almost quantitatively converted, and the requirement of atom economy is met.

Microwave-Assisted oxidation reaction of primary alcohols with sensitive functional groups to aldehydes using Ruthenium Diphosphorus Complexes

Microwave-assisted oxidation of primary alcohols to aldehydes is described using complexes with bidentate diphosphorus-xanthene ligands coordinated to Ru. The reactions took place readily at 120°C with 1 mol% catalyst loading that was generated in situ from the added [Ru(H)2(PPh3)3(CO)] and diphosphine ligands. The aldehyde yields for the benzylic alcohols were in the range 50-100%, while aliphatic alcohols gave yields of 48- 74%. For the first time, oxidation reactions under solvent-free conditions using these ligands are also presented, making the reaction greener. Other metals were also tested, and it was found that changing the metal center to Ir, Rh, or Os results in complexes that showed minimal or no activity towards the desired product.

Manganese and rhenium-catalyzed selective reduction of esters to aldehydes with hydrosilanes

The selective reduction of esters to aldehydes, via the formation of stable alkyl silyl acetals, was, for the first time, achieved with both manganese, -Mn2(CO)10- and rhenium -Re2(CO)10- catalysts in the presence of triethylsilane as reductant. These two methods provide a direct access to a large variety of aliphatic and aromatic alkyl silyl acetals (30 examples) and to the corresponding aldehydes (13 examples) upon hydrolysis. The reactions proceeded in excellent yields and high selectivity at room temperature under photo-irradiation conditions (LED, 365 nm, 40 W, 9 h).

Copper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives

A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones or aldehydes as starting materials is reported herein. Dioxygen as the sole oxidant and hexafluoroisopropanol as the solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N-O bond cleavage and C-N/C-C bond formation features high yields and broad substrate scope.