2,6-Diiodo-4-nitroaniline

Base Information

• Chemical Name: 2,6-Diiodo-4-nitroaniline
• CAS No.: 5398-27-6
• Molecular Formula: C6H4 I2 N2 O2
• Molecular Weight: 389.919
• Hs Code.: 2921420090
• European Community (EC) Number: 226-429-5
• NSC Number: 4606
• DSSTox Substance ID: DTXSID00202284
• Nikkaji Number: J217.956C
• Wikidata: Q83075559
• Mol file: 5398-27-6.mol

Synonyms:2,6-Diiodo-4-nitroaniline;5398-27-6;2.6-Diiodo-4-nitroaniline;2,6-Diiodo-4-nitroaniliine;C6H4I2N2O2;Benzenamine, 2,6-diiodo-4-nitro-;EINECS 226-429-5;4-nitro-2,6-diiodoaniline;NSC4606;2,6-diiodo-4-nitro-aniline;SCHEMBL222956;DTXSID00202284;AMY25156;NSC 4606;NSC-4606;2,6-Diiodo-4-nitroaniline, 97%;C6-H4-I2-N2-O2;(2,6-diiodo-4-nitro-phenyl)-amine;MFCD00007683;STK365756;AKOS005068295;SB83691;AS-58633;CS-0138268;D4736;FT-0635668

Chemical Property of 2,6-Diiodo-4-nitroaniline

Chemical Property:

• Appearance/Colour: yellow to green crystalline powder
• Vapor Pressure: 1.77E-08mmHg at 25°C
• Melting Point: 251-253 °C(lit.)
• Boiling Point: 430.8°Cat760mmHg
• PKA: -3.43±0.20(Predicted)
• Flash Point: 214.4°C
• PSA: 71.84000
• Density: 2.639g/cm³
• LogP: 3.49060
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 389.83622
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

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

2,6-Diiodo-4-Nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1I)N)I)[N+](=O)[O-]

Technology Process of 2,6-Diiodo-4-nitroaniline

There total 11 articles about 2,6-Diiodo-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: 94.0%

4-nitro-aniline (100-01-6,104810-17-5) → 2,6-diiodo-4-nitroaniline (5398-27-6)

Guidance literature:

With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; potassium iodide; In N,N-dimethyl-formamide; at 45 - 50 ℃; for 0.666667h;

DOI:10.1021/acs.joc.1c01642

Reference yield: 83.0%

5-nitroisatin (611-09-6) → 2,6-diiodo-4-nitroaniline (5398-27-6)

Guidance literature:

With K⁽¹⁺⁾*Cl₂I^(1-); In methanol; water; at 20 ℃; for 2191.5h;

DOI:10.1016/S0040-4039(01)00105-8

Reference yield: 65.0%

4-nitro-aniline (100-01-6,104810-17-5) → 2-iodo-4-nitrophenylamine (6293-83-0) + 2,6-diiodo-4-nitroaniline (5398-27-6)

Guidance literature:

With N-iodo-succinimide; In acetonitrile; at 40 ℃; for 0.333333h; Temperature; Solvent; regioselective reaction; Catalytic behavior;

DOI:10.1016/j.tetlet.2021.153154

upstream raw materials:

2-amino-5-nitro-benzenesulfonic acid

1,3-diiodo-2,5-dinitro-benzene

4-nitro-aniline

hydrogenchloride

Downstream raw materials:

acetic acid-(2,6-diiodo-4-nitro-anilide)

N-[5-Diethylamino-2-(2,6-diiodo-4-nitro-phenylazo)-phenyl]-acetamide

2,6-diiodo-4-nitro-N,N-dimethylaniline

2,6-diiodo-p-phenylenediamine

Refernces

• 1、 Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh. "Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes". supporting information. . Retrieved 2021/05/26.
• 2、 Dou, Shilei,Wang, Ying,Zhang, Xin. "Amphiphilic Fluorescence Resonance Energy-Transfer Dyes: Synthesis, Fluorescence, and Aggregation Behavior in Water". supporting information. p. 11503 - 11510. Retrieved 2020/08/03.