3209-13-0

Basic information

• Product Name: 3-METHOXY-5-METHYLPHENOL
• Synonyms: 3-methoxy-5-methyl-pheno;3-HYDROXY-5-METHOXYTOLUENE;3-METHOXY-5-METHYLPHENOL;5-METHOXY-M-CRESOL;ORCINOL MONOMETHYL ETHER;ORCINYL TER;TIMTEC-BB SBB008618;Methoxymethylphenol
• CAS NO: 3209-13-0
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.16
• EINECS: 221-716-1
• Product Categories: Aromatics Compounds;Aromatics;Miscellaneous Reagents
• Mol File: 3209-13-0.mol

Chemical Properties

• Melting Point: 63°C
• Boiling Point: 255.7 °C at 760 mmHg
• Flash Point: 135.6 °C
• Appearance: /
• Density: 1.078 g/cm³
• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.53
• PKA: 9.70±0.10(Predicted)
• CAS DataBase Reference: 3-METHOXY-5-METHYLPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXY-5-METHYLPHENOL(3209-13-0)
• EPA Substance Registry System: 3-METHOXY-5-METHYLPHENOL(3209-13-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-37
• WGK Germany: 2
• TSCA: Yes
• Hazardous Substances Data: 3209-13-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-METHOXY-5-METHYLPHENOL is used as a synthetic building block for the creation of various organic compounds. Its chemical structure allows it to be a versatile component in the synthesis of different molecules, making it valuable in the field of organic chemistry.
Used in Pharmaceutical Industry:
3-METHOXY-5-METHYLPHENOL is used as an intermediate in the development of pharmaceutical compounds. Its unique properties make it a promising candidate for the synthesis of new drugs, potentially leading to the discovery of novel therapeutic agents.
Used in Chemical Research:
3-METHOXY-5-METHYLPHENOL is used as a research compound in various scientific studies. Its properties and reactivity are of interest to researchers, who may use it to explore new chemical reactions and understand its potential applications in various fields.
Used in Flavor and Fragrance Industry:
3-METHOXY-5-METHYLPHENOL is used as a component in the creation of flavors and fragrances. Its unique scent profile can be utilized to develop new and innovative fragrances, as well as enhance existing ones.
Used in Material Science:
3-METHOXY-5-METHYLPHENOL can be used in the development of new materials with specific properties. Its chemical structure may contribute to the creation of materials with enhanced characteristics, such as improved stability or reactivity.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 6, p. 859, 1988The Journal of Organic Chemistry, 49, p. 1672, 1984 DOI: 10.1021/jo00183a043Tetrahedron Letters, 11, p. 1327, 1970

InChI:InChI=1/C8H10O2/c1-6-3-7(9)5-8(4-6)10-2/h3-5,9H,1-2H3

Upstream product

• 570-10-5 2-hydroxy-4-methoxy-6-methylbenzoic acid 
• 114561-50-1 acide hydroxy-2-methoxy-6-methyl-4-benzoique 
• 107783-58-4 2-hydroxy-4-methoxy-6-methyl-isophthalic acid 
• 484-55-9 thamnolic acid 
• 62-53-3 aniline 
• 504-15-4 orcinol 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 126-07-8 griseofulvin 
• 74-88-4 methyl iodide 
• 70150-66-2 5-methyl-3-hydroxycyclohex-2-enone 
• 6443-91-0 ethynyl methyl ether 
• 83897-47-6 3-Methylcyclobutenon 

Downstream Products

• 67088-25-9 Isoevernin aldehyde 
• 31405-63-7 1-(2-hydroxy-6-methoxy-4-methylphenyl)ethanone 
• 139077-39-7 3-methoxy-5-methylphenyl acetate 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 64030-63-3 2'-hydroxy-4'-methoxy-6'-methyl-propiophenone 
• 500-66-3 Olivetol 
• 142428-26-0 3-Hydroxy-2-(2-hydroxy-4-methoxy-6-methyl-benzyl)-5,6,8-trimethoxy-[1,4]naphthoquinone 
• 80393-02-8 1-oxymethylenemethoxy-3-methoxy-5-methylbenzene 
• 75895-55-5 5-methyl-5-phenyldihydroresorcinol monomethyl ether 
• 82994-07-8 3-methoxy-5-methylphenyl 2'-nitrophenyl ether 
• 82994-10-3 benzyl 4-methoxy-2-(3-methoxy-5-methylphenoxy)-6-methylbenzoate 
• 82994-13-6 5,5'-oxybis(1-methoxy-3-methylbenzene) 
• 50667-84-0 O-3-methoxy-5-methylphenyl dimethylcarbamothioate 
• 611-68-7 2-methoxy-6-methyl-1,4-benzoquinone 

Relevant articles and documents

Total Synthesis of Anti-MRSA Active Diorcinols and Analogues

Diorcinols and related prenylated diaryl ethers were reported to exhibit activity against methicillin-resistant clinical isolates of Staphylococcus aureus (MRSA). Within these lines, we report the first total synthesis of diorcinol D, I, J, the proposed structure of verticilatin and recently isolated antibacterial diaryl ether by using an efficient and highly divergent synthetic strategy. These total syntheses furnish the diaryl ethers in only five to seven steps employing a Pd-catalyzed diaryl ether coupling as the key step. The total synthesis led to the structural revision of the natural product verticilatin, which has been isolated from a plant pathogenic fungus. Furthermore, these structures were tested in order to determine their antibacterial activities against different MRSA strains as well as further Gram-positive and -negative bacteria.

A convenient, practical synthesis of substituted resorcinols: Synthesis of DB-2073 and olivetol

A wide variety of easily accesible 1,3-cyclohexanediones are readily transformed to substituted dimethyl resorcinols with iodine and methanol.

Progress towards the total synthesis of hamigerans C and D: A direct approach to an elaborated 6-7-5 carbocyclic core

The hamigeran family of natural products has been the target of numerous synthetic efforts because of its biological activity and interesting structural properties. Herein, we disclose our efforts toward the synthesis of hamigerans C and D, unique among the initially isolated members because of their 6-7-5 carbocyclic core. Our approach directly targets this tricyclic motif by sequential Negishi and Heck coupling reactions, yielding an advanced intermediate with all necessary carbons and sufficient functionality poised for completion of the synthesis of these two natural products.

Synthesis of substituted resorcinol monomethyl ethers from 2-bromo-3-methoxycyclohex-2-en-1-ones

2-Bromo-3-methoxycyclohex-2-en-1-ones are readily alkylated at C-6 with reactive halides, and then treatment with DBU (2 equiv) in PhMe at room temperature results in smooth loss of bromide and aromatization to resorcinol monomethyl ethers of defined substitution pattern.

Correlating lignin structural features to phase partitioning behavior in a novel aqueous fractionation of softwood Kraft black liquor

In this work, a set of softwood lignins were recovered from a Kraft black liquor using a novel pH-based fractionation process involving sequential CO 2 acidification and separation of the solvated aqueous lignin fraction. These recovered lignin fractions were characterized with respect to properties that may be responsible for their phase partitioning behavior as well as properties that may render the lignins more suitable for materials applications. Lignin fractions were recovered between a pH range of 12.8 and 9.5 with the bulk of the lignin (90%) recovered between a pH of 11.1 and 10.0. While all the fractions were found to consist primarily of lignin as validated by sample methoxyl content, the first fractions to phase separated were found to be especially enriched in aliphatic extractives and polysaccharides. From the bulk of the lignin that was recovered between a pH of 11.1 and 10.0 a number of noteworthy trends were discernible from the data. Specifically, the phenolic hydroxyl content was found to exhibit a strong negative correlation to the fractionation pH and exhibited a nearly 50% increase with recovery at decreasing pH, while the GPC-estimated molecular weights and 13C NMR-estimated β-O-4 content showed strong positive correlations to the pH at recovery. The aliphatic hydroxyl content exhibited minimal differences between recovery conditions. Overall, these results suggest that this fractionation approach can generate lignin fractions enriched in select physical or structural properties that may be important for their application as feedstocks for renewable chemicals or materials.

COMPOUNDS WITH 7-MEMBER CYCLE AND THE PHARMACEUTICAL USE THEREOF FOR PREVENTING AND TREATING DIABETES AND METABOLISM SYNDROME

The invention discloses a new use of a class of heptacyclic compounds in the preparation of formulations for the prevention and treatment of diabetes and metabolic syndromes; the present invention also discloses a new class of heptacyclic compounds; the present invention also discloses a process for preparing the heptacyclic compounds and a composition containing the same. The heptacyclic compounds of the present invention can be used to effectively preventing or treating diseases such as diabetes and metabolic syndromes.

Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): Scope, mechanism, and applications

The Pd-catalyzed asymmetric allylic alkylation (AAA) of phenol allyl carbonates serves as an efficient strategy to construct the allylic C-O bond allowing access to chiral chromans in up to 98% ee. The effect of pH and the influence of olefin geometry, as well as substitution pattern on the ee and the absolute configuration of the chiral chromans were explored in detail. These observations suggest a mechanism involving the cyclization of the more reactive π-allyl palladium diastereomeric intermediate as the enantiodiscriminating step (Curtin-Hammett conditions). This methodology led to the enantioselective synthesis of the vitamin E core, the first enantioselective total synthesis of (+)-clusifoliol and (-)-siccanin, and the synthesis of an advanced intermediate toward (+)-rhododaurichromanic acid A.

Imidazolyl compounds as inhibitors of farnesyl-protein tranferase

The present invention relates to inhibitors of ras farnesylation of Formula (I), wherein T is of Formula (1) or (2) or (3); A is aryl or heteroaryl; B is aryl or heteroaryl; X and Y represent hydrogen, or both X and Y can represent a single bond (so as to form a double bond); R1 represents a group of Formula (II) or (III), the group of Formula (II) or Formula (III) (having L or D configuration at the chiral alpha carbon in the corresponding free amino acid); R2 represents hydrogen, aryl or heteroaryl; Z represents a direct bond, methylene, ethylene, vinylene, oxy, —CH2—O— or —O—CH2—; and R3—R4, p and r are as defined in the specification or a pharmaceutically-acceptable salt, prodrug or solvate thereof. Processes for their preparation, their use as therapeutic agents and pharmaceutical compositions containing them. A particular use is in cancer therapy

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.

Thermal Decomposition of Lichen Depsides

The thermal decomposition of the following lichen depsides has been described: lecanoric acid, gyrophoric acid, evernic acid, perlatolic acid, planaic acid, confluentic acid, atranorin, 4-O-demethylbarbatic acid, and sekikaic acid.Main reaction products are decarboxylated compounds, phenolic units, rearranged depsides, and xanthones.Triethylammonium salts of depside carboxylic acids decompose at reasonably lower temperature than the corresponding free acids. - Keywords: Lichen Depsides, Thermal Decomposition