6702-50-7

Basic information

• Product Name: Methyl 3-hydroxy-4-methoxybenzoate
• Synonyms: METHYL 3-HYDROXY-4-METHOXYBENZENECARBOXYLATE;METHYL 3-HYDROXY-4-METHOXYBENZOATE;METHYL ISOVANILLATE;RARECHEM AL BF 0068;Methyl 3-hydroxy-4-methoxybenzoate,98%;Methyl 3-hydroxy-4-methoxybenzoateMethyl isovanillate;benzoic acid, 3-hydroxy-4-methoxy-, methyl ester;Methyl 3-hydroxy-4-m
• CAS NO: 6702-50-7
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• Product Categories: Aromatic Esters;C8 to C9;Carbonyl Compounds;Esters;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 6702-50-7.mol

Chemical Properties

• Melting Point: 64-67 °C(lit.)
• Boiling Point: 327.7 °C at 760 mmHg
• Flash Point: 132.8 °C
• Appearance: /
• Density: 1.216g/cm³
• Vapor Pressure: 0.000104mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.15±0.10(Predicted)
• CAS DataBase Reference: Methyl 3-hydroxy-4-methoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-hydroxy-4-methoxybenzoate(6702-50-7)
• EPA Substance Registry System: Methyl 3-hydroxy-4-methoxybenzoate(6702-50-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6702-50-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-hydroxy-4-methoxybenzoate is used as a starting reagent for the novel synthesis of gefitinib, an epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor. The synthesis process involves several steps, including alkylation, nitration, reduction, cyclization, chlorination, and two successive amination reactions. Methyl 3-hydroxy-4-methoxybenzoate is essential in the development of targeted cancer therapies, as gefitinib is used to treat non-small cell lung cancer and other EGFR-positive cancers.
Additionally, Methyl 3-hydroxy-4-methoxybenzoate may be used as a starting reagent in the synthesis of methyl 5-(benzo[d][1,3]dioxol-5-yl)-4-methoxy-2-nitrobenzoate, another compound with potential pharmaceutical applications.

InChI:InChI=1/C9H10O4/c1-12-8-4-3-6(5-7(8)10)9(11)13-2/h3-5,10H,1-2H3

Upstream product

• 67-56-1 methanol 
• 645-08-9 Isovanillic acid 
• 6520-86-1 4-Methoxy-4-acetoxy-3-oxo-3,4-dihydro-benzaldehyd 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 74-88-4 methyl iodide 
• 621-59-0 isovanillin 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 51673-94-0 3-hydroxy-4-methoxy-benzaldehyde (E)-oxime 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 7664-93-9 sulfuric acid 
• 2150-43-8 3,4-dihydroxybenzoic acid methyl ester 
• 74-83-9 methyl bromide 
• 121-98-2 methyl 4-methoxybenzoate 
• 591-51-5 phenyllithium 

Downstream Products

• 645-08-9 Isovanillic acid 
• 57535-57-6 methyl 3-(benzyloxy)-4-methoxy-benzoate 
• 84981-47-5 methyl 3-(n-butoxy)-4-methoxybenzoate 
• 80902-60-9 methyl 3-(1,1-dimethylprop-2-ynyloxy)-4-methoxybenzoate 
• 93757-88-1 1,2,3,4,6,7,8,9-octahydro-2,9-dicarbomethoxy-5-(2-methoxy-5-carbomethoxyphenoxy)-6-oxoisoquinoline 
• 135303-87-6 methyl 3-(4'-formylphenoxy)-4-methoxybenzoate 
• 183146-43-2 4-Methoxy-3-oxiranylmethoxy-benzoic acid methyl ester 
• 212958-38-8 3-((E)-3,7-dimethyl-octa-2,6-dienyloxy)-4-methoxy-benzoic acid methyl ester 
• 220884-51-5 methyl 4-acetoxy-4-methoxy-3-oxocyclohexa-1,5-dienecarboxylate 
• 219755-76-7 4,4-dimethoxy-3-oxo-cyclohexa-1,5-dienecarboxylic acid methyl ester 
• 97966-31-9 3-ethoxy-4-methoxybenzoic acid methyl ester 
• 380844-22-4 methyl 3-(3-chloropropoxy)-4-methoxybenzoate 
• 214472-17-0 4-methoxy-5-[3-(4-morpholinyl)propoxy]benzoic acid methyl ester 
• 573693-07-9 4-methoxycarbonyl-2-trifluoromethylsulfonyloxyanisole 

Relevant articles and documents

Rhodium-Catalyzed Twofold Unsymmetrical C-H Alkenylation-Annulation/Thiolation Reaction to Access Thiobenzofurans

A Rh(III)-catalyzed twofold unsymmetrical C-H alkenylation-annulation/thiolation reaction has been developed, enabling the straightforward and efficient synthesis of various thiobenzofurans in one step. This robust protocol proceeds with a broad substrate scope and good functional group tolerance under relatively mild reaction conditions.

Novel amide analogues of quinazoline carboxylate display selective antiproliferative activity and potent EGFR inhibition

In the present study, a novel series of quinazoline derivatives is developed for cancer therapy. All the synthesised analogues were evaluated against a panel of 60 human cancer cell lines for the antiproliferative activity. Significant and selective growth inhibition of several solid tumour cell lines such as NCI-H322M, NCI-H522 (non-small cell lung cancer), IGROV1, SK-OV-3 (ovarian cancer), TK-10 (renal cancer) and MDA-MB-468 (breast cancer) was observed. Further, all the new amide analogues strongly inhibited EGFR in low nanomolar range with morpholino quinazoline 10 producing activity (IC50 = 6.12 nM) comparable to standard drugs erlotinib and gefitinib. In addition, western blot analysis depicted inhibition of phosphorylation of EGFR by compounds 10 and 11 in MDA-MB-468 cells at 10 μM. Molecular docking studies showed the strong binding interactions with the active site of the EGFR protein. The current investigation could be extremely helpful for the development of newer therapeutically useful quinazoline based molecules for cancer therapy.

Method for synthesizing 1-(3-ethyoxyl-4-methoxy)phenyl-2-methyl-sulfonyl ethylamine

The invention discloses a method for synthesizing 1-(3-ethyoxyl-4-methoxy)phenyl-2-methyl-sulfonyl ethylamine and belongs to the technical field of organic synthesis processes. The method comprises the following steps: taking 3-hydroxy-4-methoxybenzoic acid as a raw material, carrying out an esterification reaction to obtain 3-hydroxy-4-methoxybenzoate, reacting with bromoethane to obtain 3-ethyoxyl-4-methoxybenzoate, then reacting with dimethyl sulfone to obtain 1-(3-ethyoxyl-4-methoxy)phenyl-2-methyl sulfonyl ethyl ketone, and finally carrying out a reductive amination reaction with ammoniumformate, thereby obtaining the 1-(3-ethyoxyl-4-methoxy)phenyl-2-methyl-sulfonyl ethylamine.

Sulfoximine-Assisted One-Pot Unsymmetrical Multiple Annulation of Arenes: A Combined Experimental and Computational Study

Discussed herein is an unprecedented Ru-catalyzed one-pot unsymmetrical C-H difunctionalization of arenes comprising intramolecular hydroarylation of olefins and intermolecular annulation of alkynes. This unprecedented 2-fold C-H functionalization is validated on the basis of experimental and density functional theory (DFT) study. The transformation readily occurs with the assistance of methylphenyl sulfoximine (MPS) directing group in the presence of Ru catalyst forming two C-C and one C-N bonds in a single operation. The overall process is atom economical and step-efficient and provides unusual dihydrofuran-fused isoquinolone heterocycles. Further annulation of NH and the proximal o-C-H-arene of isoquinolone with alkynes build highly conjugated novel polycyclic compounds. Overall, three independent annulations in arene motifs are visualized and thoughtfully executed; finally, 5 ring-fused structural entities are constructed forming three C-C and two C-N bonds.

NOVEL INHIBITORS OF MAP4K1

The invention relates to novel inhibitors of MAP4K1 (HPK1) useful for the treatment of diseases or disorders characterised by dysregulation of the signal transduction pathways associated with MAPK activation, including hyperproliferative diseases, diseases of immune system dysfunction, inflammatory disorders, neurological diseases, and cardiovascular diseases. The invention further relates to pharmaceutical compositions comprising the same and methods of treatment of said diseases and disorders. The inhibitors are of formula (I) wherein the definitions for A, D, E, F, R5, R6, R7, Z, ring Q, n, x and y are as given in the application.

Ortho-Quinol Acetate Chemistry: Reactivity toward Aryl-Based Nucleophiles and Applications to the Synthesis of Natural Products

Two model ortho-quinol acetates were easily prepared by iodane-mediated acetoxylative phenol dearomatization and evaluated for their reactivity toward various aryl-based nucleophiles, i.e., aryl metallic reagents and phenolic derivatives. Novel modes of reactivity, allowing the formation of biaryl linkages, were revealed and here exploited for the synthesis of two natural phenolics.

PROCESS FOR PREPARATION OF 3,4-DIHYDROXY-2-METHYL BENZOIC ACID ALKYLESTER

The present invention relates to a simple economical process for the preparation of 3,4- dihydroxy-2-methyl benzoic acid C1-4 alkyl ester and novel intermediates for use in the process.

Structure-Based Design and Biological Characterization of Selective Histone Deacetylase 8 (HDAC8) Inhibitors with Anti-Neuroblastoma Activity

Histone deacetylases (HDACs) are important modulators of epigenetic gene regulation and additionally control the activity of non-histone protein substrates. While for HDACs 1-3 and 6 many potent selective inhibitors have been obtained, for other subtypes much less is known on selective inhibitors and the consequences of their inhibition. The present report describes the development of substituted benzhydroxamic acids as potent and selective HDAC8 inhibitors. Docking studies using available crystal structures have been used for structure-based optimization of this series of compounds. Within this study, we have investigated the role of HDAC8 in the proliferation of cancer cells and optimized hits for potency and selectivity, both in vitro and in cell culture. The combination of structure-based design, synthesis, and in vitro screening to cellular testing resulted in potent and selective HDAC8 inhibitors that showed anti-neuroblastoma activity in cellular testing.

4 - (3 - chloro - 4 - fluoro benzyl amidogen) - 7 - methoxy - 6 - (3 - morpholino-propoxy) quinazoline preparation method

The invention provides a preparation method of 4-(3-chloro-4-fluorophenyl amido)-7-methoxy-6-(3-morpholine propoxy) quinazoline. Specifically, according to the method, 3-hydroxy-4-methoxybenzaldehyde (isovanillin) serves as raw materials, and the target product (I) is synthesized through the steps of oxidation, esterification, amidation, cyclization and the like. The method has the advantages of being short in synthetic route, low in cost, environmentally friendly, short in reaction step, easy to operate, high in yield and product purity and the like, and therefore the preparation method is suitable for industrial production.

Polymer supported Zn-salen complexes: An effective one-pot oxidative esterification of aldehydes to carboxylic esters

Polymer-supported Zn-salen (PS-Zn-salen) complexes were synthesized, characterized and used as a catalyst for one-pot oxidative esterification of aldehydes with alcohols. The PS-Zn-salen heterogeneous catalyst exhibited a high-performance for the oxidative esterification of aldehydes to the corresponding methyl/ethyl esters using hydrogen peroxide as a green oxidant. Due to the synergistic effect of polymer support, the heterogeneous catalyst presented superior catalytic activity and afford 100% conversion of 3,4,5-trimethoxybenzaldehyde and 4-chlorobenzaldehyde to corresponding esters under optimized conditions. The different alcohol substrates study (viz. methyl alcohol, ethyl alcohol, allyl alcohol and benzyl alcohol) showed reasonable selectivity for esters, indicating the scope of the catalysts. Significantly, the synthesized complexes possess good hydrophobic/heterogeneous properties, which permit facile reclamation of the catalyst by using mere filtration. Moreover, the effect of counter anions of complex also studied which indicated that there is no appreciable influence on the conversion of product. The catalyst was reused up to 5th successive run with the average conversion of ester 87.4%. Mechanistic studies have recognized that this “one pot” direct oxidative esterification proceeds through acid formation, proven by a GC–MS. The catalyst is also found to be very stable, up to 280?°C, confirmed by the thermo gravimetric study.