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

Description

Methyl 3-amino-4-methylbenzoate is an organic compound with the chemical formula C9H11NO2. It is a beige powder and is primarily used as a reagent in the synthesis of various compounds, including perfluoroalkylated indoles and 4-(pyrimidin-2-ylamino) benzamide derivatives, which are significant in drug development and cancer treatment.

Uses

1. Used in Drug Development:
Methyl 3-amino-4-methylbenzoate is used as a reagent for the synthesis of perfluoroalkylated indoles, which are valuable in drug development due to their potential applications in various therapeutic areas.
2. Used in Cancer Treatment:
Methyl 3-amino-4-methylbenzoate is used in the preparation of 4-(pyrimidin-2-ylamino) benzamide derivatives, which are designed as inhibitors of the hedgehog signaling pathway, a target for cancer treatment.
3. Used in Organic Synthesis:
Methyl 3-amino-4-methylbenzoate is utilized in the synthesis of various compounds, such as:
a. Methyl 4-methyl-3-((4-(proparg-1-yloxy)benzyl)amino)benzoate
b. 4-proparg-1-yloxybenzaldehyde
c. Methyl 3-amino-4-methylbenzoate
d. 4-Methyl-3-((4-(2-methylthiazol-4-yl)benzoyl)amino)benzamide
e. Methyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate
f. (5-Carbomethoxy-2-methylphenyl)(4-hydroxyphenyl)diazene
These synthesized compounds have potential applications in various fields, including pharmaceuticals, materials science, and chemical research.

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 
• 1174185-30-8 methyl 3-(2,6-dichlorobenzyloxy)benzoate 
• 19438-10-9 methyl 3-hydroxybenzoate 
• 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 
• 99-75-2 4-methyl-benzoic acid methyl ester 

Downstream Products

• 851847-27-3 methyl 3-(6-bromo-4-oxo-4H-quinazolin-3-yl)-4-methyl-benzoate 
• 851848-03-8 methyl 3-[(5-fluoro-2-nitrobenzoyl)amino]-4-methylbenzoate 
• 907574-24-7 methyl 3-(6-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate 
• 907574-31-6 6-iodo-3-[5-(methoxycarbonyl)-2-methylphenyl]-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid 
• 474330-54-6 5-amino-2-bromo-4-methylbenzoic acid methyl ester 
• 81863-45-8 3-(hydroxymethyl)-6-methylaniline 
• 586379-61-5 methyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate 
• 845884-82-4 3-amino-4-methyl-benzoic acid hydrazide 
• 1126367-24-5 methyl 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)benzoate 
• 1380281-58-2 methyl 3-((6-(2,4-difluorophenyl)pyridine-2-yl)amino)-4-methylbenzoate 
• 1094541-13-5 4-methyl-3-(3-(pyridin-3-yl)acrylamido)benzoic acid 
• 1255703-08-2 4-methyl-3-(3-(pyridin-3-yl)acrylamido)benzoyl chloride 
• 1255702-56-7 N-(4-fluorophenyl)-4-methyl-3-(3-(pyridin-3-yl)acrylamido)benzamide 
• 1395348-96-5 4-methyl-3-(2-methyl-6-morpholinopyrimidin-4-ylamino)benzoic acid 

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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