Methyl 2-amino-5-iodobenzoate

Base Information

• Chemical Name: Methyl 2-amino-5-iodobenzoate
• CAS No.: 77317-55-6
• Molecular Formula: C8H8 I N O2
• Molecular Weight: 277.062
• Hs Code.: 2922499990
• European Community (EC) Number: 616-450-1
• DSSTox Substance ID: DTXSID40357227
• Nikkaji Number: J1.424.853F
• Wikidata: Q72487006
• Mol file: 77317-55-6.mol

Synonyms:methyl 2-amino-5-iodobenzoate;77317-55-6;Methyl 5-Iodoanthranilate;5-Iodoanthranilic Acid Methyl Ester;Benzoic acid, 2-amino-5-iodo-, methyl ester;Iodoanthranilicacidmethylester;2-Amino-5-iodobenzoic Acid Methyl Ester;MFCD00798574;4-Iodo-2-(methoxycarbonyl)aniline;SCHEMBL140846;methyl-2-amino-5-iodobenzoate;DTXSID40357227;methyl 2-azanyl-5-iodanyl-benzoate;STL197501;AKOS003297664;PS-5221;2-amino-5-iodo-benzoic acid methyl ester;AC-22954;SY041013;AM20041155;CS-0150866;FT-0620513;I0516;EN300-134671;I10181;A839050;AO-080/42239455

Chemical Property of Methyl 2-amino-5-iodobenzoate

Chemical Property:

• Vapor Pressure: 0.000116mmHg at 25°C
• Melting Point: 85 °C
• Boiling Point: 335.9°C at 760 mmHg
• PKA: 1.85±0.10(Predicted)
• Flash Point: 156.9°C
• PSA: 52.32000
• Density: 1.826g/cm³
• LogP: 2.24120
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 276.95998
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

99.9% ^*data from raw suppliers

Methyl2-Amino-5-iodobenzoate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CC(=C1)I)N

Technology Process of Methyl 2-amino-5-iodobenzoate

There total 9 articles about Methyl 2-amino-5-iodobenzoate 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: 98.0%

2-carbomethoxyaniline (134-20-3) → methyl 2-amino-5-iodobenzoate (77317-55-6)

Guidance literature:

2-carbomethoxyaniline; With silver(II) sulfate; In ethanol; at 20 ℃; for 0.5h;

With iodine; In ethanol; at 20 ℃; for 1h;

DOI:10.1016/j.ejmech.2015.01.034

Reference yield: 97.0%

5-iodoisatoic anhydride (116027-10-2) → methyl 2-amino-5-iodobenzoate (77317-55-6)

Guidance literature:

With dmap; In methanol; at 60 ℃; for 3h;

DOI:10.1021/jm00119a014

Reference yield: 57.0%

2-carbomethoxyaniline (134-20-3) → methyl 2-amino-3,5-diiodobenzoate (289491-96-9) + methyl 2-amino-5-iodobenzoate (77317-55-6)

Guidance literature:

With hydrogenchloride; sodium iodine dichloride; In methanol; water; at 20 ℃; for 3h; pH=1 - 2;

DOI:10.1080/00304948.2016.1206425

upstream raw materials:

5-iodoisatoic anhydride

2-carbomethoxyaniline

methanol

2-amino-5-iodobenzoic acid

Downstream raw materials:

methyl 4-[(2,4-dichlorobenzoyl)amino]-3'-ethoxy[1,1'-biphenyl]-3-carboxylate

methyl 5-(3-carboxyphenyl)-2-[(2,4-dichlorobenzoyl)amino]benzoate

Refernces

• 1、 Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh. "Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes". supporting information. . Retrieved 2021/05/26.
• 2、 Bovonsombat, Pakorn,Lorpaiboon, Wanutcha,Laoboonchai, Sarocha,Sriprachaya-anunt, Prima,Yimkosol, Warangkana,Siriphatcharachaikul, Natthapatch,Siricharoensang, Pornpawit,Kangwannarakul, Terawee,Maeda, Jin,Losuwanakul, Satreerat,Mahesh Abhyankar, Maitraye. "A novel DMSO-assisted regioselective iodination of aniline analogues". . . Retrieved 2020/10/05.