66037-04-5

Basic information

• Product Name: Phenol, 5-bromo-2-methoxy-, acetate
• CAS NO: 66037-04-5
• Molecular Formula: C9H9BrO3
• Molecular Weight: 245.073
• Mol File: 66037-04-5.mol

Chemical Properties

• CAS DataBase Reference: Phenol, 5-bromo-2-methoxy-, acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 5-bromo-2-methoxy-, acetate(66037-04-5)
• EPA Substance Registry System: Phenol, 5-bromo-2-methoxy-, acetate(66037-04-5)

Safety Data

• Hazardous Substances Data: 66037-04-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Phenol, 5-bromo-2-methoxy-, acetate serves as a key intermediate in the synthesis of pharmaceuticals, leveraging its unique chemical properties to contribute to the development of new medications. Its ability to participate in a range of chemical reactions makes it valuable for creating diverse drug molecules.
Used in Flavor and Fragrance Industry:
Phenol, 5-bromo-2-methoxy-, acetate is utilized in the creation of flavors and fragrances, capitalizing on its capacity to impart distinctive scents and tastes. Its role in this industry is to enhance or create novel sensory experiences in consumer products.
Used in Chemical Synthesis:
Phenol, 5-bromo-2-methoxy-, acetate is employed as a precursor in chemical synthesis, facilitating the production of a variety of organic compounds. Its presence allows for specific transformations that are not easily achievable with simpler starting materials, broadening the scope of synthetic chemistry.

Upstream product

• 60444-56-6 3-acetoxy-4-methoxybenzoic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 64-19-7 acetic acid 
• 881-57-2 isovanillin acetate 
• 621-59-0 isovanillin 
• 613-70-7 2-methoxyphenyl acetate 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 108-24-7 acetic anhydride 

Downstream Products

• 1357013-33-2 (R)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-5-phenylpent-4-ynoic acid 
• 608141-44-2 R-Apremilast 
• 608141-41-9 Apremilast 
• 635705-72-5 4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 915201-13-7 (3-ethoxy-4-methoxyphenyl)boronic acid 
• 52849-52-2 1-Bromo-3-ethoxy-4-methoxybenzene 
• 243990-54-7 (3-(benzyloxy)-4-methoxyphenyl)boronic acid 
• 344762-21-6 bis(3-hydroxy-4-methoxyphenyl)methane 
• 78504-28-6 2-Benzyloxy-4-bromo-1-methoxybenzene 

Relevant articles and documents

Direct Acetoxylation of Arenes

Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism is proposed.

Synthesis of a TNF inhibitor, flurbiprofen and an: I -Pr analogue in enantioenriched forms by copper-catalyzed propargylic substitution with Grignard reagents

The copper-catalyzed substitution reaction of diethyl phosphate derived from TMSCCCH(OH)CH2CH2OTBDPS with 3-c-C5H9-4-MeOC6H3MgBr, followed by several transformations, afforded a tumor necrosis factor inhibitor possessing a Ph-acetylene moiety. The inhibitor was also synthesized from phenylacetylene phosphate PhCCCH(OP(O)(OEt)2)CH2CH2OTBDPS. Furthermore, the substitution of phosphates derived from TMSCCCH(OH)CH3 and TMSCCCH(OH)-i-Pr with 3-F-4-PhC6H3MgBr gave the corresponding substitution products, which were transformed to flurbiprofen and its i-Pr analogue, respectively. The copper-catalyzed substitutions in these syntheses proceeded in a regio- and stereoselective manner. This journal is

Methods for preparation of apremilast

The present invention discloses a method for preparation of Apremilast. β-phthalimino vinylsulfones are reacted through the asymmetric addition reaction to form an addition product, and the drug of Apremilast can be obtained from the addition product through simple reactions. The method is a process for synthesizing Apremilast in a more efficient way.

Asymmetric Synthesis of β-Aryl β-Imido Sulfones Using Rhodium Catalysts with Chiral Diene Ligands: Synthesis of Apremilast

A chiral rhodium(I)-diene catalyst enabled the one-step synthesis of β-aryl β-imido sulfones under mild reaction conditions. By selection of the chiral diene ligand L1a or L2, each enantiomer of the chiral β-aryl β-imido sulfone target can be accessed with high stereoselectivity. Demonstration of the scope of the reaction, which includes the synthesis of an N-protected chiral β-amino β-phenyl sulfone, culminated with the efficient synthesis of the heteroatom-rich active pharmaceutical ingredient apremilast.

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Synthesis of 1-[3-(Cyclopentyloxy)-4-methoxyphenyl]cyclopentanol as potential phosphodiesterase-4 inhibitor

The enzyme phosphodiesterase-4 (PDE4) plays a key role in many physiological or pathological processes in mammalian organs, where its inhibition increases cyclic adenosine monophosphate (cAMP) causing benefits in many diseases or conditions. The aim of this study is to synthesize 1-(3-(cyclopentyloxy)-4-methoxyphenyl)cyclopentanol (6) as potential phosphodiesterase-4 inhibitor. Starting from 2- methoxy phenol (1), 4-bromo-2-(cyclopentyloxy)-1-methoxybenzene (5) was synthesized in good yields. 1-[3-(Cyclopentyloxy)-4- methoxyphenyl]cyclopentanol (6) was prepared from 5 using two different methods.

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The Bromination of Phenolic Methyl Ethers with Hydrogen Bromide using Sodium Tungstate and Hydrogen Peroxide as Oxidant

Sodium tungstate has been found to be an effective catalyst for the nuclear bromination of some aromatic methyl ethers using hydrogen bromide in glacial acetic acid and hydrogen peroxide as the oxidant.