Methyl 3-amino-4-methylbenzoate

Base Information

• Chemical Name: Methyl 3-amino-4-methylbenzoate
• CAS No.: 18595-18-1
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: 29224999
• European Community (EC) Number: 606-067-8
• NSC Number: 356832
• UNII: CUK1YN8P3C
• DSSTox Substance ID: DTXSID90320269
• Nikkaji Number: J82.779G
• Wikidata: Q72487062
• Mol file: 18595-18-1.mol

Synonyms:Methyl 3-amino-4-methylbenzoate;18595-18-1;Benzoic acid, 3-amino-4-methyl-, methyl ester;CUK1YN8P3C;Methyl 3-Amino-4-Methyl-Benzoate;3-Amino-p-toluic Acid Methyl Ester;3-Amino-4-methylbenzoic Acid Methyl Ester;UNII-CUK1YN8P3C;Methyl 3-amino-p-toluate;MFCD00025206;Methyl 4-methyl-3-aminobenzoate;EC 606-067-8;NSC 356832;NSC-356832;3-amino-4-methyl-benzoic acid methyl ester;3-AMINO-4-METHYL BENZOIC ACID METHYL ESTER;Nilotinib impurity B;NSC356832;SCHEMBL85805;Methyl 3-Amion-4-Methylbenzoate;Methyl-3-amino-4-methylbenozate;YEPWCJHMSVABPQ-UHFFFAOYSA-;DTXSID90320269;CHEBI:194906;BCP24483;STR03863;STK519335;AKOS000120794;AC-7315;AC-7740;CS-W010822;SB76382;Methyl 3-amino-4-methylbenzoate, 97%;METHYL-3-AMINO-4-METHYLBENZOATE;SY003661;TS-02210;3-amino-4-methyl-benzoic acid, methyl ester;A4114;AM20030223;FT-0615065;Methyl 3-amino-4-methylbenzoate, >=98.0%;EN300-18881;J-011928;J-522139;W-206340;F1905-7181;Z104483958;NILOTINIB HYDROCHLORIDE MONOHYDRATE IMPURITY B [EP IMPURITY]

Chemical Property of Methyl 3-amino-4-methylbenzoate

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Melting Point: 113-117 °C(lit.)
• Boiling Point: 296.3 °C at 760 mmHg
• PKA: 3.31±0.10(Predicted)
• Flash Point: 152.5 °C
• Density: 1.132 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

98% ^*data from raw suppliers

Methyl 3-amino-4-methylbenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)C(=O)OC)N
• 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).

Technology Process of Methyl 3-amino-4-methylbenzoate

There total 9 articles about Methyl 3-amino-4-methylbenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

→ 3-amino-4-methyl benzoic acid methyl ester (18595-18-1)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃;

Reference yield: 96.0%

methyl 3-(1,1-dimethylethylsulfinamido)-4-methylbenzoate (1338209-75-8) → 3-amino-4-methyl benzoic acid methyl ester (18595-18-1)

Guidance literature:

methyl 3-(1,1-dimethylethylsulfinamido)-4-methylbenzoate; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 0.25h; Inert atmosphere;

With sodium hydrogencarbonate; In 1,4-dioxane; water; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.08.075

Reference yield: 94.9%

methanol (67-56-1) + 3-amino-p-toluic acid (2458-12-0) → 3-amino-4-methyl benzoic acid methyl ester (18595-18-1)

Guidance literature:

With thionyl chloride; at 5 ℃; for 6h; Reflux;

upstream raw materials:

4-methyl-3-nitro-benzoic acid methyl ester

4-methyl-benzoic acid methyl ester

methanol

3-amino-p-toluic acid

Downstream raw materials:

(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

3-((tert-butoxycarbonyl)amino)-4-methylbenzoic acid methyl ester

methyl 3-(4,6-dichloro-1,3,5-triazin-2-ylamino)-4-methylbenzoate

methyl 3-(6-bromo-4-oxo-4H-quinazolin-3-yl)-4-methyl-benzoate

Refernces

• 1、 Durner, Anna,Koufaki, Maria,Kritsi, Eftichia,Nicke, Annette,Papakostas, Alexios,T. Pournara, Dimitra,Zoumpoulakis, Panagiotis. "Design, Synthesis, and in vitro Evaluation of P2X7 Antagonists". supporting information. p. 2530 - 2543. Retrieved 2020/10/19.
• 2、 -. "Compound JK-03M having higher protein kinase G inhibitory activity or pharmaceutically acceptable salt thereof and preparation method thereof". Paragraph 0093; 0157; 0159-0160. . Retrieved 2018/11/03.