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

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

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

• 1071679-94-1 3-isocyanato-4-methyl-benzoic acid methyl ester 
• 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 
• 88072-06-4 3-(3-Bromo-propionylamino)-4-methyl-benzoic acid methyl ester 
• 895569-56-9 methyl 3-[(2-bromo-5-methoxybenzoyl)amino]-4-methylbenzoate 
• 330807-44-8 3-((tert-butoxycarbonyl)amino)-4-methylbenzoic acid methyl ester 
• 849179-92-6 methyl 3-(4,6-dichloro-1,3,5-triazin-2-ylamino)-4-methylbenzoate 
• 330807-46-0 methyl 4-(bromomethyl)-3-[(tert-butyloxycarbonyl)amino]benzoate 
• 330807-48-2 methyl 3-[(tert-butyloxycarbonyl)amino]-4-(methoxymethyl)benzoate 
• 330807-50-6 benzyl 3-[(tert-butyloxycarbonyl)amino]-4-(methoxymethyl)benzoate 
• 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 
• 851772-99-1 C₂₃H₂₄N₄O₂ 
• 851847-27-3 methyl 3-(6-bromo-4-oxo-4H-quinazolin-3-yl)-4-methyl-benzoate 

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