59908-87-1

Basic information

• Product Name: A-METHYL-3-PHENOXYBENZENEACETALDEHYDE
• Synonyms: A-METHYL-3-PHENOXYBENZENEACETALDEHYDE;2-(3-Phenoxyphenyl)propanal;α-Methyl-3-phenoxybenzeneacetaldehyde;alpha-Methyl-3-phenoxybenzeneacetaldehyde
• CAS NO: 59908-87-1
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.27
• Mol File: 59908-87-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: A-METHYL-3-PHENOXYBENZENEACETALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: A-METHYL-3-PHENOXYBENZENEACETALDEHYDE(59908-87-1)
• EPA Substance Registry System: A-METHYL-3-PHENOXYBENZENEACETALDEHYDE(59908-87-1)

Safety Data

• Hazardous Substances Data: 59908-87-1(Hazardous Substances Data)

Usage

General Description

A-Methyl-3-phenoxybenzeneacetaldehyde, also known as 3-phenoxybenzaldehyde, is a chemical compound used in the manufacturing of various products including perfumes, flavorings, and pharmaceuticals. It is a colorless to pale yellow liquid with a strong floral odor. A-Methyl-3-phenoxybenzeneacetaldehyde is also used as an intermediate in the synthesis of other organic compounds. It is a versatile chemical that is utilized in different industries for its aromatic and chemical properties. However, it is important to handle this chemical with caution as it can be hazardous if not properly managed.

Upstream product

• 201230-82-2 carbon monoxide 
• 63444-54-2 3-ethenylphenyl phenyl ether 
• 32929-75-2 2-(3-phenoxy-phenyl)-propan-1-ol 
• 32929-74-1 2-(3-Phenoxy-phenyl)-propionic acid ethyl ester 
• 80379-89-1 1-(m-phenoxyphenyl)-1-chloroethane 
• 29679-58-1 Fenoprofen 

Downstream Products

• 1226783-62-5 (2S)-2-(3-phenoxy-phenyl)-propan-1-ol 
• 31879-05-7 (R)-fenoprofen 

Relevant articles and documents

Laccase-Mediator System for Alcohol Oxidation to Carbonyls or Carboxylic Acids: Toward a Sustainable Synthesis of Profens

By combining two green and efficient catalysts, such as the commercially available enzyme laccase from Trametes versicolor and the stable free radical 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), the oxidation in water of some primary alcohols to the corresponding carboxylic acids or aldehydes and of selected secondary alcohols to ketones can be accomplished. The range of applicability of bio-oxidation is widened by applying the optimized protocol to the oxidation of enantiomerically pure 2-arylpropanols (profenols) into the corresponding 2-arylpropionic acids (profens), in high yields and with complete retention of configuration.

Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (s)-profens

Described is an efficient heterologous expression system for Sulfolobus solfataricus ADH-10 (Alcohol Dehydrogenase isozyme 10) and its use in the dynamic reductive kinetic resolution (DYRKR) of 2-arylpropanal (Profen-type) substrates. Importantly, among the 12 aldehydes tested, a general preference for the (S)-antipode was observed, with high ee's for substrates corresponding to the NSAIDs (nonsteroidal anti-inflammatory drugs) naproxen, ibuprofen, flurbiprofen, ketoprofen, and fenoprofen. To our knowledge, this is the first application of a dehydrogenase from this Sulfolobus hyperthermophile to asymmetric synthesis and the first example of a DYRKR with such an enzyme. The requisite aldehydes are generated by Buchwald-Hartwig-type Pd(0)-mediated α-arylation of tert-butyl propionate. This is followed by reduction to the aldehyde in one [lithium diisobutyl tert-butoxyaluminum hydride (LDBBA)] or two steps [LAH/Dess-Martin periodinane]. Treatment of the profenal substrates with SsADH in 5% EtOH/phosphate buffer, pH 9, with catalytic NADH at 80 °C leads to efficient DYRKR, with ee's exceeding 90% for 9 aryl side chains, including those of the aforementioned NSAIDs. An in silico model, consistent with the observed broad side chain tolerance, is presented. Importantly, the SsADH-10 enzyme could be conveniently recycled by exploiting the differential solubility of the organic substrate/product at 80 °C and at rt. Pleasingly, SsADH-10 could be taken through several thermal cycles, without erosion of ee, suggesting this as a generalizable approach to enzyme recycling for hyperthermophilic enzymes. Moreover, the robustness of this hyperthermophilic DH, in terms of both catalytic activity and stereochemical fidelity, speaks for greater examination of such archaeal enzymes in asymmetric synthesis.

Method for producing (aryl substituted) carboxylic acid or its salt

An effective method for producing highly pure (aryl substituted)carboxylic acid or its salt which comprises the steps of: (I) oxidizing (aryl substituted)aldehyde in an acidic phase in the presence of hypohalogenite; and (II) bringing the oxidized product obtained in the preceding step into contact in a liquid phase with hydrogen in the presence of a catalyst of transistion metal of the group VIII in the periodic table.