Methyl 2-(methylamino)benzoate

Base Information

• Chemical Name: Methyl 2-(methylamino)benzoate
• CAS No.: 85-91-6
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: 2922499990
• European Community (EC) Number: 201-642-6
• NSC Number: 9406
• UNII: 5Z37T562P9
• DSSTox Substance ID: DTXSID1052581
• Nikkaji Number: J2.411B
• Wikidata: Q27263085
• Metabolomics Workbench ID: 46395
• ChEMBL ID: CHEMBL1409791
• Mol file: 85-91-6.mol

Synonyms:methyl N-methylanthranilate

Chemical Property of Methyl 2-(methylamino)benzoate

Chemical Property:

• Appearance/Colour: Clear to yellowish liquid
• Vapor Pressure: 0.0193mmHg at 25°C
• Melting Point: 17-19 °C(lit.)
• Refractive Index: n20/D 1.579(lit.)
• Boiling Point: 252.4 °C at 760 mmHg
• PKA: 2.80±0.10(Predicted)
• Flash Point: 106.5 °C
• PSA: 38.33000
• Density: 1.125 g/cm³
• LogP: 1.58790
• Storage Temp.: Store below +30°C.
• Solubility.: Miscible in all proportions with ethanol 96%, DMSO and diethyl e
• Water Solubility.: 329.792mg/L at 30℃
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

99.9% ^*data from raw suppliers

Methyl N-Methylanthranilate >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: CNC1=CC=CC=C1C(=O)OC
• Description: Methyl n-methylanthranilate has an orange and mandarin peel-like odor with a musty, grape-like flavor. It is somewhat more berry-like than grape. May be prepared by methylation of methyl anthranilate or esterification of N-methylanthranilic acid.
• Uses: It is used as a flavorant in a wide range of foods (particularly flour and sugar confections). Methyl 2-(Methylamino)benzoate is one of many volatile components from mango cultivars.

Technology Process of Methyl 2-(methylamino)benzoate

There total 57 articles about Methyl 2-(methylamino)benzoate 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: 92.0%

methanol (67-56-1) + N-Methylisatoic anhydride (10328-92-4) → Methyl N-methylanthranilate (85-91-6)

Guidance literature:

With sulfuric acid; for 3h; Reagent/catalyst; Reflux;

DOI:10.1016/j.tet.2016.03.059

Reference yield: 90.0%

methyl 2-(methyl(nitroso)amino)benzoate (68061-82-5) → benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + 4-nitrobenzoic acid methyl ester (619-50-1) + diphenic acid dimethyl ester (5807-64-7) + dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate (55676-77-2) + dimethyl (1,1'-biphenyl)-2,3'-dicarboxylate (32947-58-3) + 2-(benzoyl-methylamino)benzoic acid methyl ester (75541-61-6) + 2-carbomethoxyaniline (134-20-3) + Methyl N-methylanthranilate (85-91-6) + methyl 2-(benzamido)benzoate (7510-49-8) + N-formylanthranilic acid methyl ester (41270-80-8)

Guidance literature:

at 220 ℃; for 0.25h; Sealed tube;

DOI:10.1039/c5ra07612a

Reference yield: 86.0%

methyl 2-((tert-butoxycarbonyl)(methyl)amino)benzoate → Methyl N-methylanthranilate (85-91-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

upstream raw materials:

methanol

N-Methylanthranilic acid

N-Methylisatoic anhydride

2-carbomethoxyaniline

Downstream raw materials:

1-methyl-3-(3-trifluoromethyl-anilinomethyl)-2,3-dihydro-1H-benzo[e][1,4]oxazepin-5-one

1-Methyl-3-(2-methylamino-benzoyl)-pyrrolidinon-2

1-Phenyl-3-(2-methylamino-benzoyl)-pyrrolidinon-2

1-Benzyl-3-(2-methylamino-benzoyl)-piperidon-2

Refernces

• 1、 Wang, Lei,Fang, Kun,Cheng, Junfei,Li, Yu,Huang, Yahui,Chen, Shuqiang,Dong, Guoqiang,Wu, Shanchao,Sheng, Chunquan. "Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer". . p. 696 - 713. Retrieved 2020/02/04.
• 2、 Roell, Daniela,R?sler, Thomas W.,Hessenkemper, Wiebke,Kraft, Florian,Hauschild, Monique,Bartsch, Sophie,Abraham, Tsion E.,Houtsmuller, Adriaan B.,Matusch, Rudolf,van Royen, Martin E.,Baniahmad, Aria. "Halogen-substituted anthranilic acid derivatives provide a novel chemical platform for androgen receptor antagonists". . p. 59 - 70. Retrieved 2019/02/01.