104-09-6

Basic information

• Product Name: P-METHYLPHENYLACETALDEHYDE
• Synonyms: (4-Methylphenyl)acetaldehyde;(4-methyl-phenyl)-acetaldehyde;4-methyl-benzeneacetaldehyd;4-methyl-Benzeneacetaldehyde;4-methyl-phenyl-acetaldehyde;benzeneacetaldehyde,-methyl-;4-TOLYLACETALDEHYDE;2-P-TOLYLACETALDEHYDE
• CAS NO: 104-09-6
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• EINECS: 203-173-2
• Product Categories: Benzene derivatives;Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het
• Mol File: 104-09-6.mol
• Article Data: 99

Chemical Properties

• Melting Point: 40°C
• Boiling Point: 221.5°C (estimate)
• Flash Point: 102.1 °C
• Appearance: /
• Density: 1.0052
• Vapor Pressure: 0.115mmHg at 25°C
• Refractive Index: 1.5255 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: P-METHYLPHENYLACETALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-METHYLPHENYLACETALDEHYDE(104-09-6)
• EPA Substance Registry System: P-METHYLPHENYLACETALDEHYDE(104-09-6)

Safety Data

• Hazardous Substances Data: 104-09-6(Hazardous Substances Data)

Usage

Chemical Properties

p-Tolylacetaldehyde has a characteristic green fruity odor reminiscent of sweet floral and forest-like and a corresponding flavor.

Preparation

From p-methylbenzaldehyde; also from p-methylbenzyl chloride and hexamethylene tetramine.

Taste threshold values

Taste characteristics at 10 ppm: sweet, fruity cherry with spicy an nutty nuances.

Synthesis Reference(s)

Synthetic Communications, 17, p. 677, 1987 DOI: 10.1080/00397918708075741

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

Upstream product

• 13107-39-6 2-(4-methylphenyl)oxirane 
• 696-61-7 4-tolylmagnesium chloride 
• 149-73-5 trimethyl orthoformate 
• 193883-13-5 (E)-(4-methylstyryl)(phenyl)sulfide 
• 7647-01-0 hydrogenchloride 
• 2947-61-7 (4-methylphenyl)acetonitrile 
• 60-29-7 diethyl ether 
• 104-81-4 4-Methylbenzyl bromide 
• 2344-80-1 Chloromethyltrimethylsilane 
• 14062-19-2 p-tolylacetic acid ethyl ester 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 111-34-2 -butyl vinyl ether 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 

Downstream Products

• 14471-79-5 6-chloro-3-(4-methyl-benzyl)-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-benzo[1,2,4]thiadiazine-7-sulfonic acid amide 
• 135628-91-0 (Z)-3-Methyl-2-((E)-2-p-tolyl-vinyl)-pent-2-enedioic acid 1-methyl ester 
• 106-42-3 para-xylene 
• 13938-94-8 bis(triphenylphosphine)carbonylrhodium(I) chloride 
• 108-88-3 toluene 
• 92631-27-1 6-p-tolylhex-1-en-5-ol 
• 622-47-9 4-tolylacetic acid 
• 917873-52-0 4-p-tolyl-thiophene-2-carboxylic acid ethyl ester 
• 1345882-89-4 ethyl 2-amino-5-(4-methylphenyl)-3-thiophenecarboxylate 
• 1374667-33-0 2-oxo-N,N'-2-tri(p-tolyl)acetimidamide 
• 37009-57-7 2-phenyl-5-p-tolyloxazole 
• 17286-62-3 2-(4-methylphenyl)quinoxaline 
• 1571070-58-0 4-methyl-1-p-tolyl-1H-quinolizin-2(9aH)-one 
• 1571070-71-7 4,6-dimethyl-1-p-tolyl-1H-quinolizin-2(9aH)-one 

Relevant articles and documents

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The selective oxidation of alcohols to the corresponding aldehydes and ketones is of great importance in the academic and industrial fields. A series of excellent nanostructured catalysts comprising cobalt nanoparticles supported on nitrogen-doped carbon (Co-N-C) were thus prepared by pyrolysis of a deep eutectic solvent Co(NO3)2·6H2O/[Bmim]Br supported on commercial carbon. The catalytic activity of the Co-N-C materials was studied in the selective aerobic oxidation of alcohols with molecular oxygen under base-free conditions. The results indicated that the optimized Co-N-C/700 catalyst exhibited excellent catalytic performance in the selective oxidation of both aryl and alkyl alcohols, giving their corresponding aldehydes and ketones in good to excellent yields. Furthermore, the combination of the catalytic results of the control group and the different characterization methods showed that such high catalytic activity is due to the synergistic interaction between the nitrogen-doped carbon support and Co-N species in Co-N-C/700. In addition, the magnetically recoverable Co-N-C catalyst could be easily separated from the reaction system by using an external magnetic field and reused at least five times without an obvious decrease in the catalytic efficiency.

Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes

Biocatalytic anti-Markovnikov alkene hydroamination and hydration were achieved based on two concepts involving enzyme cascades: epoxidation-isomerization-amination for hydroamination and epoxidation-isomerization-reduction for hydration. An Escherichia coli strain coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI), ω-transaminase (CvTA), and alanine dehydrogenase (AlaDH) catalyzed the hydroamination of 12 aryl alkenes to give the corresponding valuable terminal amines in high conversion (many ≥86%) and exclusive anti-Markovnikov selectivity (>99:1). Another E. coli strain coexpressing SMO, SOI, and phenylacetaldehyde reductase (PAR) catalyzed the hydration of 12 aryl alkenes to the corresponding useful terminal alcohols in high conversion (many ≥80%) and very high anti-Markovnikov selectivity (>99:1). Importantly, SOI was discovered for stereoselective isomerization of a chiral epoxide to a chiral aldehyde, providing some insights on enzymatic epoxide rearrangement. Harnessing this stereoselective rearrangement, highly enantioselective anti-Markovnikov hydroamination and hydration were demonstrated to convert α-methylstyrene to the corresponding (S)-amine and (S)-alcohol in 84-81% conversion with 97-92% ee, respectively. The biocatalytic anti-Markovnikov hydroamination and hydration of alkenes, utilizing cheap and nontoxic chemicals (O2, NH3, and glucose) and cells, provide an environmentally friendly, highly selective, and high-yielding synthesis of terminal amines and alcohols.

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Treatment of a novel polymer-supported phenylselenomethyltrimethylsilane reagent with LDA followed by alkylation and oxidative deselenation efficiently afforded aliphatic aldehydes in moderate to good yields with excellent purities. Copyright Taylor & Francis Group, LLC.

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Catalytic epoxidation of styrene with molecular oxygen is regarded as an eco-friendly alternative to producing industrially important chemical of styrene oxide (STO). Recent efforts have been focused on developing highly active and stable heterogeneous catalysts with high STO selectivity for the aerobic epoxidation of styrene. Herein, a series of transition metal monosubstituted heteropolyacid compounds (TM-HPAs), such as Fe, Co, Ni or Cu-monosubstituted HPA, were encapsulated in UiO-66 frameworks (denoted as TM-HPA@UiO-66) by direct solvothermal method, and their catalytic properties were investigated for the aerobic epoxidation of styrene with aldehydes as co-reductants. Among them, Co-HPA@UiO-66 showed relatively high catalytic activity, stability and epoxidation selectivity at very mild conditions (313 K, ambient pressure), that can achieve 82 % selectivity to STO under a styrene conversion of 96 % with air as oxidant and pivalaldehyde (PIA) as co-reductant. In addition, the hybrid composite catalyst can also efficiently catalyze the aerobic epoxidation of a variety of styrene derivatives. The monosubstituted Co atoms in Co-HPA@UiO-66 are the main active sites for the aerobic epoxidation of styrene with O2/PIA, which can efficiently converting styrene to the corresponding epoxide through the activation of the in-situ generated acylperoxy radical intermediate.

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