2-Bromo-3-nitroanisole

Base Information

• Chemical Name: 2-Bromo-3-nitroanisole
• CAS No.: 67853-37-6
• Molecular Formula: C7H6BrNO3
• Molecular Weight: 232.034
• Hs Code.: 2909309090
• European Community (EC) Number: 806-649-3
• DSSTox Substance ID: DTXSID80590419
• Wikidata: Q72448458
• Mol file: 67853-37-6.mol

Synonyms:2-Bromo-3-nitroanisole;2-bromo-1-methoxy-3-nitrobenzene;67853-37-6;Benzene, 2-bromo-1-methoxy-3-nitro-;MFCD07779272;2-Bromo-3-methoxynitrobenzene;2-bromo-3-nitro-anisole;SCHEMBL1059260;DTXSID80590419;CL8586;AKOS015851795;AB42485;CS-W001123;PS-5705;AC-22670;SY045479;DB-008168;A9074;AM20080625;EN300-137917;AN-584/43409807;J-508238

Chemical Property of 2-Bromo-3-nitroanisole

Chemical Property:

• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.581
• Boiling Point: 273.274 °C at 760 mmHg
• Flash Point: 119.072 °C
• PSA: 55.05000
• Density: 1.64 g/cm³
• LogP: 2.88910
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 230.95311
• Heavy Atom Count: 12
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-3-nitroanisole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1Br)[N+](=O)[O-]

Technology Process of 2-Bromo-3-nitroanisole

There total 4 articles about 2-Bromo-3-nitroanisole 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: 94.0%

2-bromo-3-hydroxy-1-nitrobenzene (101935-40-4) + methyl iodide (74-88-4) → 2-bromo-1-methoxy-3-nitrobenzene (67853-37-6)

Guidance literature:

With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 18 - 22 ℃;

Reference yield: 50.0%

2-methoxy-6-nitroaniline (16554-45-3) → 2-bromo-1-methoxy-3-nitrobenzene (67853-37-6)

Guidance literature:

2-methoxy-6-nitroaniline; With hydrogen bromide; sodium nitrite; In water; at 0 ℃; for 0.666667h;

With copper(I) bromide; In water; at 0 - 60 ℃; for 2h; Heating / reflux;

Reference yield:

2-Amino-3-nitrophenol (603-85-0) → 2-bromo-1-methoxy-3-nitrobenzene (67853-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / K₂CO₃ / dimethylformamide / 20 °C

2: NaNO₂; aq. H₂SO₄; CuBr / aq. HBr

With sulfuric acid; potassium carbonate; copper(I) bromide; sodium nitrite; hydrogen bromide; In N,N-dimethyl-formamide; 2: Sandmeyer reaction;

DOI:10.1021/jm051146h

upstream raw materials:

2-bromo-3-hydroxy-1-nitrobenzene

dimethyl sulfate

2-methoxy-6-nitroaniline

2-Amino-3-nitrophenol

Downstream raw materials:

phenazin-1-ol

1-methoxyphenazine

2-(6'-methanesulfonyl-2'-pyridin-4-yl-biphenyl-4-yloxymethyl)-quinoline

6-pyridin-4-yl-4'-(quinolin-2-ylmethoxy)-biphenyl-2-ylamine

Refernces

• 1、 -. "Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof". Page/Page column 67. . Retrieved 2010/11/26.
• 2、 Zhang, Lin,Fan, Junhua,Vu, Khang,Hong, Kevin,Le Brazidec, Jean-Yves,Shi, Jiandong,Biamonte, Marco,Busch, David J.,Lough, Rachel E.,Grecko, Roy,Ran, Yingqing,Sensintaffar, John L.,Kamal, Adeela,Lundgren, Karen,Burrows, Francis J.,Mansfield, Robert,Timony, Gregg A.,Ulm, Edgar H.,Kasibhatla, Srinivas R.,Boehm, Marcus F.. "7′-Substituted benzothiazolothio- and pyridinothiazolothio-purines as potent heat shock protein 90 inhibitors". . p. 5352 - 5362. Retrieved 2007/10/03.