6395-18-2

Basic information

• Product Name: Methyl 2,3,4-trimethoxybenzoate
• Synonyms: Methyl 2,3,4-trimethoxybenzoate
• CAS NO: 6395-18-2
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.22586
• Mol File: 6395-18-2.mol

Chemical Properties

• Boiling Point: 320.5±37.0 °C(Predicted)
• Appearance: /
• Density: 1.134±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Methyl 2,3,4-trimethoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,4-trimethoxybenzoate(6395-18-2)
• EPA Substance Registry System: Methyl 2,3,4-trimethoxybenzoate(6395-18-2)

Safety Data

• Hazardous Substances Data: 6395-18-2(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 56128-66-6 2,3,4-trihydroxybenzoic acid methyl ester 
• 610-02-6 2,3,4-trihydroxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 1968-71-4 methyl 2-bromo-3,4,5-trimethoxybenzoate 
• 80141-07-7 methyl 6-bromo-2,3,4-trimethoxybenzoate 
• 573-11-5 2,3,4-Trimethoxy-benzoic acid 
• 75-91-2 tert.-butylhydroperoxide 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 67-56-1 methanol 
• 7169-07-5 3,4,5-(trimethoxy)benzoyl chloride 
• 634-36-6 1,2,3-trimethoxybenzene 
• 56128-24-6 2,3-dihydroxy-4-methoxybenzoic acid methyl ester 

Downstream Products

• 1752-00-7 methyl 2,3,4-trimethoxy-6-nitrobenzoate 
• 573-11-5 2,3,4-Trimethoxy-benzoic acid 
• 94169-66-1 methyl 5-chloromethyl-2,3,4-trimethoxybenzoate 
• 114605-73-1 methyl 5-bromo-2,3,4-trimethoxybenzoate 
• 208043-53-2 [2-(3,5-Dichloro-pyridin-4-yl)-1-oxoethyl]-2,3-dihydroxy-4-methoxybenzene 
• 56128-24-6 2,3-dihydroxy-4-methoxybenzoic acid methyl ester 
• 1153791-73-1 C₁₀H₁₄N₂O₄ 
• 1153263-59-2 5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole-2-thiol 
• 31821-78-0 3-(3,4,5-trimetossifenil)-4-ammino-5-mercapto-4H-1,2,4-triazolo 
• 1035572-17-8 1-(3-ethoxy-2,4-dimethoxyphenyl)-2-(3,5-dichloro-pyridin-4-yl)ethanone 
• 1035572-18-9 1-(3-cyclopropylmethoxy-2,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone 
• 1035571-41-5 1-(2-benzyloxy-3,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone 
• 1035571-40-4 2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxy-2-phenethyloxyphenyl)ethanone 
• 1035571-52-8 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(3-phenylpropoxy)phenyl]ethanone 

Relevant articles and documents

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A series of 3,6-diaryl-[1,2,4]triazolo[4,3-b]pyridazines were designed as a class of vinylogous CA-4 analogues. The easily isomerized (Z,E)-butadiene linker of vinylogous CA-4 was replaced by a rigid [1,2,4]triazolo[4,3-b]pyridazine scaffold. Twenty-one target compounds were synthesized and exhibited moderate to potent antiproliferative activity. The compound 4q with a 3-amino-4-methoxyphenyl moiety as the B-ring, comparable to CA-4 (IC50 = 0.009-0.012 μM), displayed the highly active antiproliferative activity against SGC-7901, A549, and HT-1080 cell lines with IC50 values of 0.014, 0.008, and 0.012 μM, respectively. Tubulin polymerization experiments indicated that 4q effectively inhibited tubulin polymerization, and immunostaining assay revealed that 4q significantly disrupted tubulin microtubule dynamics. Moreover, cell cycle studies revealed that compound 4q dramatically arrested cell cycle progression at G2/M phase in A549 cells. Molecular modeling studies showed that 4q could bind to the colchicine binding site on microtubules.

Copper-catalyzed methyl esterification reactions via C-C bond cleavage

The highly effective synthesis of methyl esters from benzylic alcohols, aldehydes, or acids via copper-catalyzed C-C cleavage from tert-butyl hydroperoxide is reported in this paper for the first time. Our protocol is easily accessible and practical, making it a possible supplement for the traditional way.

Process development of the PDE4 inhibitor K-34

A short and practical synthesis of the PDE4 inhibitor K-34 (1) was developed. This synthesis was achieved in four steps and with a 58% overall yield. The unique spiro acetal was created with exceptionally high yield by utilizing the neighbor carboxylic acid assistance. This synthesis also features efficient ketone construction with 4-pyridinylmethyl anion 9 and ester 18, in which overreaction should be prohibited by quick in situ enolate formation. The overall synthesis was carried out under mild conditions and used a simple procedure suitable for large-scale production.

Synthesis, characterization and antifungal activity of some 5-substituted 4-amino-1,2,4-triazole-3-thiols

A series of 5-substituted 4-amino-1,2,4-triazole-3-thiols (4a-i) was synthesized by refluxing substituted organic acids (a-i) with methanol to the corresponding esters (1a-i). These esters were then converted to hydrazides (2a-i) by reaction with hydrazine hydrate in the presence of absolute ethanol. The hydrazides were then converted to 5-substituted 1,3,4-oxadiazole-2-thiols (3a-i) by cyclization reaction with carbon disulfide and KOH which was followed by reaction with hydrazine hydrate in the presence of absolute ethanol. Structure of the synthesized compounds was established by physico-chemical and spectral data analysis. Synthesized compounds were subjected to antifungal activity. Antifungal activity analysis was performed against Aspergillus flavus, Mucor species, Aspergillus niger and Aspergillus fumigates, with test compounds at a concentration of 200 μg/mL. Terbinafine was used as the standard drug.

SUBSTITUTED ACETOPHENONES USEFUL AS PDE4 INHIBITORS

The present invention relates to a compound according to formula: (I); wherein X1, X2, X3, X4 and X5 independently of each other represent -CH- or N; or X3, X4 and X5

Derivatives of benzofuran or benzodioxole

An oxygen-containing heterocyclic compound represented by following Formula (I): wherein R1and R2independently represent hydrogen, lower alkyl, cyano, —(CH2)n—E1—CO—G1(wherein E1represents a bond, O, or NH; and G1represents hydrogen, substituted or unsubstituted lower alkyl, OR6, or NR7R8; and n represents an integer of 0 to 4), or the like; R1and R2are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R2, and R11or R13described below are combined to form a single bond; R3represents hydrogen, phenyl, or halogen; R4represents hydroxy, lower alkoxy, or the like; A represents —C(R9)(R10)— or O; B represents O, NR11, —C(R12)(R13)—, or —C(R14)(R15)—C(R16)(R17)—; D represents (i) —C(R18)(R19)—X— (wherein X represents —C(R21)(R22)—, S, or NR23), (ii) —C(R19a)═Y— [Y represents —C(R24)—Z— (wherein Z represents CONH, CONHCH2, or a bond), or N], or (iii) a bond; and R5represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or pharmaceutically acceptable salts thereof.

DERIVATIVES OF BENZOFURAN OR BENZODIOXOLE

An oxygen-containing heterocyclic compound represented by following Formula (I): wherein R1 and R2 independently represent hydrogen, lower alkyl, cyano, —(CH2)n—E1—CO—G1 (wherein E1 represents a bond, O, or NH; and G1 represents hydrogen, substituted or unsubstituted lower alkyl, OR6, or NR7R8; and n represents an integer of 0 to 4), or the like; R1 and R2 are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R2, and R11 or R13 described below are combined to form a single bond; R3 represents hydrogen, phenyl, or halogen; R4 represents hydroxy, lower alkoxy, or the like; A represents —C(R9)(R10)— or O; B represents O, NR11, —C(R12)(R13)—, or —C(R14)(R15)—C(R16)(R17)—; D represents (i) —C(R18)(R19)—X— (wherein X represents —C(R21)(R22)—, S, or NR23), (ii) —C(R19a)═Y— [Y represents —C(R24)—Z— (wherein Z represents CONH, CONHCH2, or a bond), or N], or (iii) a bond; and R5 represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or pharmaceutically acceptable salts thereof.

OXYGENIC HETEROCYCLIC COMPOUNDS

Oxygen-containing heterocyclic compounds represented by following Formula (I): wherein n represents an integer of 1 to 4; R1, R2, R3and R4are the same or different and represent hydrogen, substituted or unsubstituted lower alkyl, or the like; R5represents hydrogen or halogen; R6represents hydroxy or substituted or unsubstituted lower alkoxy; D represents (1) -C(R8)(R9)-X- or (2) a bond; R7represents (1) substituted or unsubstituted lower alkyl, substituted or unsubstituted cycloalkyl, polycycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted heterocyclic group, or pyridine-N-oxide, (2) -Y-ZR14, (3) -Y-Z-(CH2)m-N(R16a)R16b, or (4) -Y-CON(R17a)R17b, or pharmaceutically acceptable salts thereof.

Manganese(III)-Mediated Formylation of Aromatic Compounds in the Presence of Malonic Acid

The reaction of naphthlenes with malonic acid in the presence of manganese(III) acetate gives naphthalenecarbaldehydes and naphthalenecarboxylic acids.Similar reactions of anthracene, pyrene, and methoxybenzenes also yield formylated and carboxylated products.It was found that the formyl group introduced to the aromatic ring was not derived from carboxymethyl radical generated directly by the thermolysis of manganese(III) acetate, but from a dicarboxymethyl radical formed by the interaction of malonic acid and manganese(III) acetate.In addition, it was also found that the dicarboxymethyl radicals attacked the position of the highest electron density on the aromatic ring and that this formylation was effective when the ionization potential of the aromatic copound was lower than 7.8 eV.

2-(Piperazinyl)-4-pyrimioinamines

Herein is disclosed 2-(1-piperazinyl)-4-pyrimidinamine derivatives, acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions of the derivatives. The derivatives are distinguished most readily by having novel substituents at position 4 of the piperazinyl radical, the substituents being selected from the group consisting of optionally substituted 2-cycloheptimidazolyl, 1,4,5,6,7,8-hexahydrocycloheptimidazol-2-yl, 2-benzoxazolyl, benzthiazol-2-yl, 1H-2-benzimidazolyl and 1-oxo-2,4,6-cycloheptarien-2-yl. The derivatives are useful for treating hypertension in a mammal.