20734-74-1

Basic information

• Product Name: 2-hydroxy-4-Methoxytoluene
• Synonyms: 2-hydroxy-4-Methoxytoluene;5-Methoxy-2-Methylphenol
• CAS NO: 20734-74-1
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.1638
• Mol File: 20734-74-1.mol

Chemical Properties

• Melting Point: 44 °C
• Boiling Point: 249-250 °C
• Appearance: /
• Density: 1.078±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.93±0.10(Predicted)
• CAS DataBase Reference: 2-hydroxy-4-Methoxytoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-4-Methoxytoluene(20734-74-1)
• EPA Substance Registry System: 2-hydroxy-4-Methoxytoluene(20734-74-1)

Safety Data

• Hazardous Substances Data: 20734-74-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 3741, 1988 DOI: 10.1016/S0040-4039(00)82103-6

Upstream product

• 50868-72-9 5-methoxy-o-toluidine 
• 104-93-8 p-methylanizole 
• 67-56-1 methanol 
• 150-19-6 O-methylresorcine 
• 17484-36-5 4-Methyl-3-nitroanisole 
• 698-27-1 4-methylsalicylaldehyde 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 616-38-6 carbonic acid dimethyl ester 
• 108-46-3 recorcinol 
• 426835-03-2 3-methoxy-6-methyl-2-cyclohexenone trimethylsilyl enol ether 
• 496-73-1 4-methyl resorcinol 
• 77-78-1 dimethyl sulfate 
• 19217-50-6 4-methyl-3-(methyloxy)phenol 
• 62536-84-9 2-formyl-5-methoxyphenyl acetate 

Downstream Products

• 855754-07-3 Methyl-(6-nitro-3-hydroxy-4-methyl-phenyl)-aether 
• 91061-91-5 2-Acetoxy-5-methoxy-2-methyl-cyclohexadien-(3,5)-on-⁽¹⁾ 
• 614-13-1 2-methoxy-5-methyl-1,4-benzoquinone 
• 1025975-22-7 2-(2,2-diethoxy-ethoxy)-4-methoxy-1-methyl-benzene 
• 55027-74-2 2,4-dibromo-3-methoxy-6-methylphenol 
• 928632-56-8 C₃₆H₄₈N₄O₃ 
• 478613-41-1 C₂₇H₃₇N₃O₃ 

Relevant articles and documents

Photochemical Lumiketone-Type Rearrangement of 3-Methoxyphenol Promoted by AlBr3

Irradition of 3-methoxyphenol in the presence of 2 equiv. of AlBr3 in CH2Cl2 gave 4-methoxybicyclohex-3-en-2-one in a 38percent yield. 3-Methoxy-2-methylphenol also yielded the lumiketone rearrangement product.On the other hand, 3-methoxy-4-methyl-, 3-methoxy-5-methyl-, and 5-methoxy-2-methylphenol underwent transposition of the methyl group to give equilibrium mixtures of the three methoxycresoles.

Enantioselective synthesis of bicyclo[2.2.2]octenones using a copper-mediated oxidative dearomatization/[4 + 2] dimerization cascade

An enantioselective approach to bicyclo[2.2.2]octenone structures utilizing a copper-mediated asymmetric oxidative dearomatization/[4 + 2] dimerization cascade is described. The total synthesis and absolute stereochemistry reassignment of (+)-aquaticol has been achieved using the methodology. Copyright

A convenient synthesis of phenols

Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Metal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism

Methods for carbon-hydrogen (C-H) bond oxidation have a fundamental role in synthetic organic chemistry, providing functionality that is required in the final target molecule or facilitating subsequent chemical transformations. Several approaches to oxidizing aliphatic C-H bonds have been described, drastically simplifying the synthesis of complex molecules. However, the selective oxidation of aromatic C-H bonds under mild conditions, especially in the context of substituted arenes with diverse functional groups, remains a challenge. The direct hydroxylation of arenes was initially achieved through the use of strong Bronsted or Lewis acids to mediate electrophilic aromatic substitution reactions with super-stoichiometric equivalents of oxidants, significantly limiting the scope of the reaction. Because the products of these reactions are more reactive than the starting materials, over-oxidation is frequently a competitive process. Transition-metal-catalysed C-H oxidation of arenes with or without directing groups has been developed, improving on the acid-mediated process; however, precious metals are required. Here we demonstrate that phthaloyl peroxide functions as a selective oxidant for the transformation of arenes to phenols under mild conditions. Although the reaction proceeds through a radical mechanism, aromatic C-H bonds are selectively oxidized in preference to activated-H bonds. Notably, a wide array of functional groups are compatible with this reaction, and this method is therefore well suited for late-stage transformations of advanced synthetic intermediates. Quantum mechanical calculations indicate that this transformation proceeds through a novel addition-abstraction mechanism, a kind of 'reverse-rebound' mechanism as distinct from the common oxygen-rebound mechanism observed for metal-oxo oxidants. These calculations also identify the origins of the experimentally observed aryl selectivity.

Dehydrative C-H alkylation and alkenylation of phenols with alcohols: Expedient synthesis for substituted phenols and benzofurans

A well-defined cationic Ru-H complex catalyzes the dehydrative C-H alkylation reaction of phenols with alcohols to form ortho-substituted phenol products. Benzofuran derivatives are efficiently synthesized from the dehydrative C-H alkenylation and annulation reaction of phenols with 1,2-diols. The catalytic C-H coupling method employs cheaply available phenols and alcohols, exhibits a broad substrate scope, tolerates carbonyl and amine functional groups, and liberates water as the only byproduct.

IMIDAZOLIDINEDIONE DERIVATIVES

The invention provides a compound of formula (Ia), and pharmaceutically acceptable salts thereof. The invention also provides use of the compounds or salts as modulators of Kv3.1 and/or Kv3.2, and in the treatment of diseases or disorders where a modulator of Kv3.1 and/or Kv3.2 is required, such as depression and mood disorders, hearing disorders, schizopherenea, substance abuse disorders, sleep disorders or epilepsy.

HETEROCYCLIC NON-PEPTIDE GNRH ANTAGONISTS

A compound of formula (I): wherein either B is absent and A and Z are the same or different and are each hydrogen, halogen, alkyl, hydroxy, alkoxy,-CN,-C(Rc)2OH,-N(Rd)C(=X)Rc,-C(=X)N(Rc)(Rd),-S(O)m-Rc,-N(Rc)(Rd)S(O)2,-S(O)2N(R c)(Rd),-N(Re)2, aryl optionally substituted with Ra or-O-aryl optionally substituted with Ra; or B is present and is-(CH2)n-,-C(Rb)2-or-O-, or B taken together with A or Z can be-C=C(Rb)-,-C(Rb)=C-,-CH2-CH(R b)-or-CH(Rb)-CH2-; D is-O-or-S(O) m,-; E is a bond or is-(CH2)n-,-N(R d)-,-(CH2)nN(Rd)-or-N(R d)(CH2)n-; F is-C(=X)-; G is-(CH2 )n-,-N(Rd)-,-(CH2)nN(R d)-or-N(Rd)(CH2)n; J is a bond,-O-,-N(RC)C(=X)-,-C(=X)N(Rc)-,-S(O)m,-,-N(Rc)S(O)m-,-S(O)nN(Rc)-,-N(Re)-or-N(Rg)(Rh); K is a bond, alkylene, cycloalkylene, cycloalkenylene, arylene, heterocycloalkylene, heterocycloalkylene or heteroarylene; and L is hydrogen or a terminal group; has therapeutic utility.

Selective production of methoxyphenols from dihydroxybenzenes on alkali metal ion-loaded MgO

Selective O-methylation of dihydroxybenzenes (DHBs; catechol, resorcinol, and hydroquinone) to methoxyphenols (MPs) was carried out with dimethylcarbonate on MgO and alkali metal ion (Li, K, and Cs)-loaded MgO between 523 and 603 K. Catalytic activity and product selectivity varied with respect to DHB substrates. Selectivity for O-methylated products increased with increasing basicity of alkali ions; however, K-MgO showed high and stable activity toward MPs. Selectivity for MPs obtained from three substrates increased in the following order: catechol 2 followed by air and 13C CP-MAS NMR measurements indicated the nature of deposited carbon to be molecular species, graphite, MgCO3 and polyaromatics. XPS revealed the nature and availability of active sites on the spent catalysts, as well as the same changes with reaction conditions and correlated with catalytic activity.

PHENOXYETHER DERIVATIVES AS PPAR MODULATORS

The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR), such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.