4-Bromo-5-methoxy-2-nitroaniline

Base Information

• Chemical Name: 4-Bromo-5-methoxy-2-nitroaniline
• CAS No.: 173312-36-2
• Molecular Formula: C7H7BrN2O3
• Molecular Weight: 247.048
• Hs Code.: 2922299090
• European Community (EC) Number: 804-840-6
• DSSTox Substance ID: DTXSID40445113
• Nikkaji Number: J2.249.408B
• Wikidata: Q82263449
• Mol file: 173312-36-2.mol

Synonyms:4-BROMO-5-METHOXY-2-NITROANILINE;173312-36-2;4-bromo-5-methoxy-2-nitro-aniline;Benzenamine, 4-bromo-5-methoxy-2-nitro-;SCHEMBL4268905;DTXSID40445113;JYXJPWNTXBYKMD-UHFFFAOYSA-N;2-Nitro-4-bromo-5-methoxyaniline;YGA31236;MFCD13659425;AKOS015835326;CS-0309883;EN300-187994;P19063

Chemical Property of 4-Bromo-5-methoxy-2-nitroaniline

Chemical Property:

• Boiling Point: 368.4±37.0 °C(Predicted)
• PKA: -1.44±0.25(Predicted)
• PSA: 81.07000
• Density: 1.718±0.06 g/cm3(Predicted)
• LogP: 3.05250
• Storage Temp.: Room temperature.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 245.96400
• Heavy Atom Count: 13
• Complexity: 197

Purity/Quality:

≥95% ^*data from raw suppliers

4-Bromo-5-methoxy-2-nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)N)[N+](=O)[O-])Br
• Uses: 4-Bromo-5-methoxy-2-nitroaniline, is an intermediate in the synthesis of novel benzimidazoles Urea, acting as inhibitors of DNA Gyrase and Topoisomerase IV, possessing potent antibacterial activity.

Technology Process of 4-Bromo-5-methoxy-2-nitroaniline

There total 11 articles about 4-Bromo-5-methoxy-2-nitroaniline 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: 93.0%

4'-bromo-5'-methoxy-2'-nitroacetanilide (173312-35-1) → 4-bromo-5-methoxy-2-nitrobenzeneamine (173312-36-2)

Guidance literature:

With hydrogenchloride; acetic acid; for 1h; Heating;

DOI:10.1002/jhet.5570320523

Reference yield: 89.0%

5-methoxy-2-nitroaniline (16133-49-6) → 4-bromo-5-methoxy-2-nitrobenzeneamine (173312-36-2)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; Inert atmosphere; Reflux;

Reference yield:

1-bromo-2-methoxy-4-nitrobenzene (77337-82-7) → 4-bromo-5-methoxy-2-nitrobenzeneamine (173312-36-2)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 5percent Pd/C / ethyl acetate

3: KNO₃

4: 10percent NaOH / ethanol / Heating

With sodium hydroxide; hydrogen; potassium nitrate; palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1016/0040-4039(95)01562-V

upstream raw materials:

N-(4-bromo-5-methoxy-2-nitrophenyl)-2,2,2-trifluoroacetamide

4'-bromo-5'-methoxy-2'-nitroacetanilide

1-acetamido-5-methoxy-2nitrobenzene

m-Anisidine

Downstream raw materials:

N-(4-Bromo-5-methoxy-2-nitro-phenyl)-oxalamic acid ethyl ester

1-bromo-4-iodo-2-methoxy-5-nitrobenzene

N-(5-bromo-2-iodo-4-methoxyphenyl)-2,2,2-trifluoroacetamide

N-[2-(6-bromo-5-methoxy-1H-indol-3-yl)ethyl]-N-methylsulfanyloxymethoxy-2-nitrobenzenesulfonamide

Refernces

• 1、 -. "METHODS AND COMPOSITIONS FOR MODULATING SPLICING". Paragraph 0620; 0717. . Retrieved 2020/08/22.
• 2、 -. "HETEROCYCLIC AND HETEROARYL COMPOUNDS FOR TREATING HUNTINGTON'S DISEASE". Page/Page column 170. . Retrieved 2020/01/24.