Methyl 3-amino-5-bromobenzoate

Base Information

• Chemical Name: Methyl 3-amino-5-bromobenzoate
• CAS No.: 706791-83-5
• Molecular Formula: C8H8BrNO2
• Molecular Weight: 230.061
• Hs Code.: 2922499990
• European Community (EC) Number: 849-036-6
• DSSTox Substance ID: DTXSID90596068
• Wikidata: Q72438413
• Mol file: 706791-83-5.mol

Synonyms:Methyl 3-amino-5-bromobenzoate;706791-83-5;MFCD07786958;3-amino-5-bromo-benzoic acid methyl ester;Benzoic acid,3-amino-5-bromo-, methyl ester;3-AMINO-5-BROMOBENZOIC ACID METHYL ESTER;Methyl3-amino-5-bromobenzoate;SCHEMBL176618;methyl-3-amino-5-bromobenzoate;methyl 3-amino-5-bromo-benzoate;DTXSID90596068;MNXLJDUZJCMJCI-UHFFFAOYSA-N;TD1096;TD1371;AKOS012323115;CS-W019455;AC-28541;DS-18641;SY034474;DB-074333;EN300-179872;J-650242;Z1079174444

Chemical Property of Methyl 3-amino-5-bromobenzoate

Chemical Property:

• Melting Point: 83-88℃
• Boiling Point: 332.308 °C at 760 mmHg
• PKA: 2.38±0.10(Predicted)
• Flash Point: 154.775 °C
• PSA: 52.32000
• Density: 1.578 g/cm³
• LogP: 2.39910
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 228.97384
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 3-amino-5-bromobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 3-amino-5-bromobenzoate

There total 5 articles about Methyl 3-amino-5-bromobenzoate 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%

methanol (67-56-1) + 3-amino-5-bromobenzoic acid (42237-85-4) → 3-amino-5-bromobenzoic acid methyl ester (706791-83-5)

Guidance literature:

With thionyl chloride; at 0 - 70 ℃; for 4h; Inert atmosphere;

Reference yield: 99.0%

methyl 3-bromo-5-nitrobenzoate (6307-87-5) → 3-amino-5-bromobenzoic acid methyl ester (706791-83-5)

Guidance literature:

methyl 3-bromo-5-nitrobenzoate; With hydrogenchloride; iron; In ethanol; water; for 5h; Reflux;

With sodium carbonate; In methanol; water;

DOI:10.1016/j.tet.2010.08.049

Reference yield:

3-bromo-5-nitro-benzoic acid (6307-83-1) → 3-amino-5-bromobenzoic acid methyl ester (706791-83-5)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 6 h / 0 °C / Reflux

2: tin(ll) chloride / tetrahydrofuran; ethanol / 6 h / 0 °C / Reflux

With thionyl chloride; tin(ll) chloride; In tetrahydrofuran; ethanol;

DOI:10.1021/jo102160x

upstream raw materials:

methyl 3-bromo-5-nitrobenzoate

methyl 3-nitrobenzoate

methanol

3-amino-5-bromobenzoic acid

Downstream raw materials:

3-bromo-5-(4-chlorobutanoylamino)benzoic acid methyl ester

methyl 3-bromo-5-(thiophene-2-carboxamido)benzoate

methyl 3-bromo-5-[2-(thiophen-2-yl)acetamido]benzoate

methyl 3-bromo-5-acetylaminobenzoate

Refernces

• 1、 Haberhauer, Gebhard,Burkhart, Christoph,Woitschetzki, Sascha,W?lper, Christoph. "Light and chemically driven molecular machines showing a unidirectional four-state switching cycle". . p. 1887 - 1895. Retrieved 2015.
• 2、 Jung, Young-Hwan,Salmaso, Veronica,Wen, Zhiwei,Bennett, John M.,Phung, Ngan B.,Lieberman, David I.,Gopinatth, Varun,Randle, John C. R.,Chen, Zhoumou,Salvemini, Daniela,Karcz, Tadeusz P.,Cook, Donald N.,Jacobson, Kenneth A.. "Structure-Activity Relationship of Heterocyclic P2Y14Receptor Antagonists: Removal of the Zwitterionic Character with Piperidine Bioisosteres". . p. 5099 - 5122. Retrieved 2021/05/05.