2,5-Dibromo-4-nitroaniline

Base Information

• Chemical Name: 2,5-Dibromo-4-nitroaniline
• CAS No.: 25462-68-4
• Molecular Formula: C6H4Br2N2O2
• Molecular Weight: 295.918
• Hs Code.: 2921420090
• DSSTox Substance ID: DTXSID90457049
• Nikkaji Number: J88.359J
• Wikidata: Q82279731
• Mol file: 25462-68-4.mol

Synonyms:2,5-dibromo-4-nitroaniline;25462-68-4;SCHEMBL3718211;DTXSID90457049;KUASSBMCIQLDOH-UHFFFAOYSA-N;AB9030;BBL025685;MFCD14582986;STL367720;AKOS000447132;AS-44938;CS-0170891;A877579

Chemical Property of 2,5-Dibromo-4-nitroaniline

Chemical Property:

• Melting Point: 180-181.5 °C(Solv: ethanol (64-17-5))
• Boiling Point: 356.2±37.0 °C(Predicted)
• PKA: -2.25±0.14(Predicted)
• PSA: 71.84000
• Density: 2.177±0.06 g/cm3(Predicted)
• LogP: 3.80640
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 295.86190
• Heavy Atom Count: 12
• Complexity: 185

Purity/Quality:

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

2,5-Dibromo-4-nitroaniline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1Br)[N+](=O)[O-])Br)N

Technology Process of 2,5-Dibromo-4-nitroaniline

There total 8 articles about 2,5-Dibromo-4-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: 97.0%

N-(2,5-dibromo-4-nitrophenyl)acetamide (25462-67-3) → 2,5-dibromo-4-nitroaniline (25462-68-4)

Guidance literature:

With hydrogenchloride; In water; for 41h; Reflux; Inert atmosphere;

DOI:10.1002/asia.201600673

Reference yield:

N-(2,5-dibromophenyl)acetamide (25462-66-2) → 2,5-dibromo-4-nitroaniline (25462-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / HNO₃; H₂SO₄ / -20 - 20 °C

2: 88 percent / K₂CO₃ / CH₂Cl₂; methanol / 3 h

With sulfuric acid; nitric acid; potassium carbonate; In methanol; dichloromethane;

DOI:10.1016/j.tet.2003.10.089

Reference yield:

2,5-dibromoaniline (3638-73-1) → 2,5-dibromo-4-nitroaniline (25462-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 27 g / Et₃N / 1 h / 35 °C

2: 63 percent / HNO₃; H₂SO₄ / -20 - 20 °C

3: 88 percent / K₂CO₃ / CH₂Cl₂; methanol / 3 h

With sulfuric acid; nitric acid; potassium carbonate; triethylamine; In methanol; dichloromethane;

DOI:10.1016/j.tet.2003.10.089

upstream raw materials:

2,5-dibromoaniline

1,4-dibromo-2,5-dinitro-benzene

ammonia

N-(2,5-dibromo-4-nitrophenyl)acetamide

Downstream raw materials:

4-nitro-2,5-bis(trimethylsilanylethynyl)phenylamine

4-bromo-2,5-dinitro-4'-phenylethynyl-biphenyl

4''-ethynyl-2',5'-dinitro-4-phenylethynyl-[1,1';4',1'']terphenyl

(2',5'-dinitro-4-phenylethynyl-[1,1';4',1'']terphenyl-4''-ylethynyl)-trimethyl-silane

Refernces

• 1、 Wilson, Danielle,Djukic, Brandon,Lemaire, Martin T.. "Synthesis of bromine- or aryl-substituted ditopic Schiff base ligands and their bimetallic iron(II) complexes: Electronic and magnetic properties". . p. 17 - 24. Retrieved 2014/03/21.
• 2、 Wang, Changsheng,Batsanov, Andrei S.,Bryce, Martin R.,Sage, Ian. "An improved synthesis and structural characterisation of 2-(4-acetylthiophenylethynyl)-4-nitro-5-phenylethynylaniline: The molecule showing high negative differential resistance (NDR)". . p. 2089 - 2095. Retrieved 2007/10/03.