Methyl 3-amino-4-methylbenzoate

Methyl 3-amino-4-methylbenzoate
  • CAS No.:18595-18-1

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  1. This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
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Methyl 3-amino-4-methylbenzoate Basic information
Product Name:Methyl 3-amino-4-methylbenzoate
Synonyms:METHYL 3-AMINO-4-METHYLBENZOATE;METHYL 3-AMINO-P-TOLUATE;LABOTEST-BB LT00848257;3-amino-2,4-dimethylbenzoate;Nilotinib Impurity 25;Nilotinib EP Impurity B;3-Amino-p-Toluic Acid Methyl Ester 3-Amino-4-Methyl Benzoic Acid Methyl Ester;3-Amino-4-Methylbenzoate
CAS:18595-18-1
MF:C9H11NO2
MW:165.19
EINECS:606-067-8
Product Categories:Building Blocks;C8 to C9;Aromatic Esters;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;FINE Chemical & INTERMEDIATES;Acids and Derivatives;Amines and Anilines;Esters;Phenyls & Phenyl-Het;bc0001
Mol File:18595-18-1.mol
Methyl 3-amino-4-methylbenzoate Chemical Properties
Melting point 113-117 °C(lit.)
Boiling point 296.3±20.0 °C(Predicted)
density 1.132±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Chloroform (Slightly), Methanol (Slightly)
pka3.31±0.10(Predicted)
form Crystalline Powder
color White to cream
BRN 2088611
InChIKeyYEPWCJHMSVABPQ-UHFFFAOYSA-N
LogP1.7 at 22℃ and pH7
CAS DataBase Reference18595-18-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37
WGK Germany 3
Hazard Note Irritant
HS Code 29224999
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Methyl 3-amino-4-methylbenzoate Usage And Synthesis
Chemical PropertiesBeige powder
UsesMethyl 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).
ApplicationMethyl 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.
PreparationSynthesis 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)

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