2-Bromo-6-nitrophenol

Base Information

• Chemical Name: 2-Bromo-6-nitrophenol
• CAS No.: 13073-25-1
• Molecular Formula: C6H4BrNO3
• Molecular Weight: 218.007
• Hs Code.: 29089990
• European Community (EC) Number: 629-309-4
• DSSTox Substance ID: DTXSID40926876
• Nikkaji Number: J707.360G
• Wikidata: Q72448649
• Mol file: 13073-25-1.mol

Synonyms:2-Bromo-6-nitrophenol;13073-25-1;Phenol, 2-bromo-6-nitro-;2-Bromo-6-nitro-phenol;6-Nitro-2-bromophenol;MFCD02683216;2-Brom-6-Nitrophenol;2-nitro-6-bromo-phenol;SCHEMBL846242;2-Bromo-6-nitrophenol, 97%;DTXSID40926876;BCP13329;GEO-00526;AKOS008901368;AKOS040756631;AC-3171;CS-W021626;HY-W040886;PS-6258;PD158375;SY004223;AM20060355;B2203;EN300-111276;AE-641/03312018;Q-101065

Chemical Property of 2-Bromo-6-nitrophenol

Chemical Property:

• Appearance/Colour: bright yellow powder
• Vapor Pressure: 0.052mmHg at 25°C
• Melting Point: 66-70 °C(lit.)
• Refractive Index: 1.652
• Boiling Point: 227.2 °C at 760 mmHg
• PKA: 5.36±0.24(Predicted)
• Flash Point: 91.2 °C
• PSA: 66.05000
• Density: 1.881 g/cm³
• LogP: 2.58610
• Storage Temp.: Room temperature.
• Solubility.: Chloroform; Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 216.93746
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-6-nitrophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Br)O)[N+](=O)[O-]
• Uses: 2-Bromo-6-nitrophenol is an intermediate used in the synthesis of N-Hydroxy Eltrombopag (H825795), which is a derivative compound of Eltrombopag (508000), an agonist of the Thrombopoietin (Tpo) receptor, used as treatment for thrombocytopenia.

Technology Process of 2-Bromo-6-nitrophenol

There total 16 articles about 2-Bromo-6-nitrophenol 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: 86.0%

2-hydroxynitrobenzene (88-75-5,78813-12-4) → 4-bromo-2-nitrophenol (7693-52-9) + 2-bromo-6-nitro-phenol (13073-25-1)

Guidance literature:

With Oxone; potassium bromide; In methanol; at 20 ℃; for 24h;

DOI:10.1081/SCC-120006001

Reference yield: 85.0%

2-bromo-6-nitrophenol t-butylamine salt (100782-02-3) → 2-bromo-6-nitro-phenol (13073-25-1)

Guidance literature:

With sulfuric acid; Heating;

Reference yield: 83.0%

2-hydroxybromobenzene (95-56-7) → 2-bromo-6-nitro-phenol (13073-25-1)

Guidance literature:

With trichloroisocyanuric acid; bismuth subnitrate/charcoal; In dichloromethane; at 20 ℃; for 2h; regioselective reaction;

DOI:10.1016/j.cclet.2010.05.016

upstream raw materials:

2-hydroxybromobenzene

acetic acid

2-hydroxynitrobenzene

piperidine

Downstream raw materials:

2-amino-6-bromophenol hydrochloride

2-bromo-4-chloro-6-nitro-phenol

2-bromo-4,6-dinitrophenol

2,4-dibromo-6-nitrophenol

Refernces

• 1、 Mustafa, Shaik,Santhosh Reddy,Surendra Babu. "Unexpected one pot C (aryl)-N bond cleavage and Questiomycin A formation from the reduction reaction of 2-amino-6-nitrophenol derivatives". . p. 6104 - 6107. Retrieved 2015.
• 2、 -. "Preparation method of Eltrombopag key intermediate 3'-amino-2'-hydroxybiphenyl-3-carboxylic acid". Paragraph 0019; 0020. . Retrieved 2019/11/20.
• 3、 -. "Novel method for preparing Eltrombopag intermediate". Paragraph 0059-0061. . Retrieved 2017/04/29.