18595-18-1

Basic information

• Product Name: Methyl 3-amino-4-methylbenzoate
• Synonyms: METHYL 3-AMINO-4-METHYLBENZOATE;METHYL 3-AMINO-P-TOLUATE;LABOTEST-BB LT00848257;AKOS BB-3092;3-AMINO-4-METHYLBENZOIC ACID METHYL ESTER;3-AMINO-P-TOLUIC ACID METHYL ESTER;3-Amino-p-Toluic Acid Methyl Ester 3-Amino-4-Methyl Benzoic Acid Methyl Ester;3-Amino-4-Methylbenzoate
• CAS NO: 18595-18-1
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• Product Categories: FINE Chemical & INTERMEDIATES;Acids and Derivatives;Amines and Anilines;Aromatic Esters;Esters;Phenyls & Phenyl-Het;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 18595-18-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 113-117 °C(lit.)
• Boiling Point: 296.3 °C at 760 mmHg
• Flash Point: 152.5 °C
• Appearance: White to cream/Crystalline Powder
• Density: 1.132 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.31±0.10(Predicted)
• BRN: 2088611
• CAS DataBase Reference: Methyl 3-amino-4-methylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-amino-4-methylbenzoate(18595-18-1)
• EPA Substance Registry System: Methyl 3-amino-4-methylbenzoate(18595-18-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 18595-18-1(Hazardous Substances Data)

Usage

Chemical Properties

Beige powder

Uses

Methyl 3-Amino-4-methylbenzoate is used as a reagent in the synthesis of perfluoroalkylated indoles which are very useful in drug development. It was also used in the preparation of 4-(pyrimidin-2-ylamino) benzamide derivatives which are designed as inhibitors of hedgehog signalling pathway (target of cancer treatment).

Application

Methyl 3-amino-4-methylbenzoate can be used for:To prepare the methyl 4-methyl-3-((4-(proparg-1-yloxy)benzyl)amino)benzoate, 4-proparg-1-yloxybenzaldehyde (16) and methyl 3-amino-4-methylbenzoate were reacted according to the method IA. Synthesis of Methyl 4-methyl-3-((4-(2-methylthiazol-4-yl)benzoyl)amino)benzoateSynthesis of 4-Methyl-3-((4-(2-methylthiazol-4-yl)benzoyl)amino)benzamideSynthesis of methyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1 (2H)-yl)-4-methylbenzoateSynthesis of (5-Carbomethoxy-2-methylphenyl)(4-hydroxypheny)diazene: To a solution of 6N HC1 (6 mL) was added methyl 3-amino-4-methylbenzoate (1.62 g, 10.0 mmol). The solution was cooled in an ice-bath, and was diazotized by adding sodium nitrite (0.9 g, 12.0 mmol). To a cold solution of phenol in 21% aqueous NaOH solution (6 mL) was added diazotized solution slowly. After 20 min, the solution was acidfied by adding 4 N aqueous HC1 and was poured into the cold water, filtered, and washed with water. Recrystallization from ethanol gave the product (2.0 g, 74%) as red crystals, mp 181.3-182.2 °C.

Preparation

Synthesis of Methyl 3-amino-4-methylbenzoate: Nitro ester Methyl 4-methyl-3-nitrobenzoate (80 g, 0.410 mol) was subjected to hydrogenation in a Parr shaker in MeOH using Raney Ni as the catalyst (5 g, 20 mol %) at 50 psi for 8 hours. The catalyst was filtered off, washed thoroughly with MeOH and the combined filtrates concentrated under reduced pressure to furnish a yellow solid (65.0 g). Yield : 96% Mp : 114-5°C (lit.14 Mp 116°C)

Upstream product

• 7356-11-8 4-methyl-3-nitro-benzoic acid methyl ester 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 1174185-30-8 methyl 3-(2,6-dichlorobenzyloxy)benzoate 
• 96-98-0 4-methyl-3-nitrobenzoic acid 
• 104901-43-1 methyl 3-bromo-4-methylbenzoate 
• 1338209-75-8 methyl 3-(1,1-dimethylethylsulfinamido)-4-methylbenzoate 
• 67-56-1 methanol 
• 2458-12-0 3-amino-p-toluic acid 

Downstream Products

• 849179-92-6 methyl 3-(4,6-dichloro-1,3,5-triazin-2-ylamino)-4-methylbenzoate 
• 99326-78-0 3-((1S,5R,7S)-7-Chlorocarbonyl-1,5,7-trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]non-3-yl)-4-methyl-benzoic acid methyl ester 
• 903292-70-6 methyl 3-(3,4-dimethoxybenzamido)-4-methylbenzoate 
• 845884-82-4 3-amino-4-methyl-benzoic acid hydrazide 
• 951627-58-0 4-methyl-3-[(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)amino]benzoic acid 
• 773104-00-0 methyl 3-[(aminocarbonothioyl)amino]-4-methylbenzoate 
• 885518-82-1 methyl 3-iodo-1H-indazole-6-carboxylate 
• 99309-16-7 (1S,5R,7S)-3-(5-Methoxycarbonyl-2-methyl-phenyl)-1,5,7-trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid 
• 1071679-94-1 3-isocyanato-4-methyl-benzoic acid methyl ester 

Relevant articles and documents

Synthesis, structure-activity relationships, cocrystallization and cellular characterization of novel smHDAC8 inhibitors for the treatment of schistosomiasis

Schistosomiasis is a major neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy consists of mass treatment with the only available drug, praziquantel. In this study, we chemically optimized our previously reported benzhydroxamate-based inhibitors of Schistosoma mansoni histone deacetylase 8 (smHDAC8). Crystallographic analysis provided insights into the inhibition mode of smHDAC8 activity by the highly potent inhibitor 5o. Structure-based optimization of the novel inhibitors was carried out using the available crystal structures as well as docking studies on smHDAC8. The compounds were evaluated in screens for inhibitory activity against schistosome and human HDACs (hHDAC). The in vitro and docking results were used for detailed structure activity relationships. The synthesized compounds were further investigated for their lethality against the schistosome larval stage using a fluorescence-based assay. The most promising inhibitor 5o showed significant dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.

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