Methyl N-formylanthranilate

Base Information

• Chemical Name: Methyl N-formylanthranilate
• CAS No.: 41270-80-8
• Molecular Formula: C9H9NO3
• Molecular Weight: 179.175
• European Community (EC) Number: 255-287-7
• UNII: XHM71YC88Y
• DSSTox Substance ID: DTXSID4068294
• Nikkaji Number: J320.039F
• Wikidata: Q27293842
• Metabolomics Workbench ID: 45488
• Mol file: 41270-80-8.mol

Synonyms:Methyl N-formylanthranilate;41270-80-8;methyl 2-formamidobenzoate;Methyl 2-(formylamino)benzoate;Benzoic acid, 2-(formylamino)-, methyl ester;Methyl 2-formylaminobenzoate;UNII-XHM71YC88Y;XHM71YC88Y;EINECS 255-287-7;2-Formylamino-benzoic acidmethylester;N-formylanthranilic acid methyl ester;methyl2-formamidobenzoate;methyl 2-ormamidobenzoate;methyl formyl anthranilate;Methyl-N-formyl-anthranilat;SCHEMBL2442267;DTXSID4068294;FEMA NO. 4171;METHYL O-FORMAMIDOBENZOATE;CHEBI:165204;methyl 2 - (formylamino)benzoate;MFCD08457073;STL301875;AKOS005199060;2-formylamino-benzoic acid methyl ester;2-(Formylamino)benzoic acid methyl ester;AS-58992;METHYL N-FORMYLANTHRANILATE [FHFI];CS-0327406;J-521869;Q27293842

Chemical Property of Methyl N-formylanthranilate

Chemical Property:

• Vapor Pressure: 1.33E-05mmHg at 25°C
• Refractive Index: 1.578
• Boiling Point: 367.8 °C at 760 mmHg
• PKA: 14.39±0.70(Predicted)
• Flash Point: 176.3 °C
• PSA: 58.89000
• Density: 1.243 g/cm³
• LogP: 1.69100
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 193

Purity/Quality:

99%, ^*data from raw suppliers

Methyl2-formamidobenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC=C1NC=O

Technology Process of Methyl N-formylanthranilate

There total 8 articles about Methyl N-formylanthranilate 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%

formic acid (64-18-6) + 2-carbomethoxyaniline (134-20-3) → N-formylanthranilic acid methyl ester (41270-80-8)

Guidance literature:

With sulfated polyborate; In neat (no solvent); at 70 ℃; for 0.5h;

DOI:10.1007/s13738-017-1186-x

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: 90.0%

formic acid (64-18-6) + 2-ethoxycarbonylaniline (87-25-2) → N-formylanthranilic acid methyl ester (41270-80-8)

Guidance literature:

With (1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium)₃[PW₁₂O₄₀^3-]; In neat (no solvent); at 70 ℃; for 1.5h; Green chemistry;

DOI:10.1016/j.tet.2014.02.042

upstream raw materials:

formic acid

2-carbomethoxyaniline

formic acid ethyl ester

3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide

Downstream raw materials:

2-(2-(2-(2-(dimethylamino)benzamido)-N-phenethylacetamido)-3-methylbutanamido)benzoic acid

2-(2-(N-(4-chlorobenzyl)-2-(2-(dimethylamino)benzamido)acetamido)-3-methylbutanamido)benzoic acid

2-(2-(2-(2-(dimethylamino)benzamido)-N-(4-fluorobenzyl)acetamido)-3-methylbutanamido)benzoic acid

2-(2-(N-benzyl-2-(2-(dimethylamino)benzamido)acetamido)-3-methylbutanamido)benzoic acid

Refernces

• 1、 Khatri, Chetan K.,Chaturbhuj, Ganesh U.. "Sulfated polyborate-catalyzed N-formylation of amines: a rapid, green and efficient protocol". . p. 2513 - 2519. Retrieved 2017/11/06.
• 2、 Miltojevi?, Ana B.,Radulovi?, Niko S.. "Structural elucidation of thermolysis products of methyl N-methyl-N-nitrosoanthranilate". . p. 53569 - 53585. Retrieved 2015/06/30.