3,5-Diiodoaniline

Base Information

• Chemical Name: 3,5-Diiodoaniline
• CAS No.: 35122-96-4
• Molecular Formula: C6H5I2N
• Molecular Weight: 344.921
• European Community (EC) Number: 846-467-1
• DSSTox Substance ID: DTXSID50478250
• Nikkaji Number: J1.245.220I
• Wikidata: Q82311493
• Mol file: 35122-96-4.mol

Synonyms:3,5-DIIODOANILINE;35122-96-4;3,5-Diiodoanaline;MFCD01851092;Benzenamine, 3,5-diiodo-;C6H5I2N;SCHEMBL222780;DTXSID50478250;CHLBMXJABUVAJX-UHFFFAOYSA-N;AKOS027384309;SB83362;AS-37546;SY151723;CS-0308612;FT-0702804;EN300-125750;A904996

Chemical Property of 3,5-Diiodoaniline

Chemical Property:

• PKA: pK1:2.37(+1) (25°C)
• PSA: 26.02000
• LogP: 3.05920
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 344.85114
• Heavy Atom Count: 9
• Complexity: 87.1

Purity/Quality:

97% ^*data from raw suppliers

3,5-Diiodoanaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C=C(C=C1I)I)N
• Uses: 3,5-Diiodoanaline is used as a reactant in the preparation of triiodobenzene for the synthesis of phenylacetlene-based conjugated dendrimers with unsymmetrical branching.

Technology Process of 3,5-Diiodoaniline

There total 8 articles about 3,5-Diiodoaniline 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%

3,5-diiodonitrobenzene (57830-60-1) → 3,5-diiodoaniline (35122-96-4)

Guidance literature:

3,5-diiodonitrobenzene; With sodium dithionite; In 2-methoxy-ethanol; water; for 3h; Heating;

With hydrogenchloride; In 2-methoxy-ethanol; water; for 1h; Further stages.; Heating;

DOI:10.1021/ja003990x

Reference yield:

2,6-diiodo-4-nitroaniline (5398-27-6) → 3,5-diiodoaniline (35122-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaNO₂; H₂SO₄ / 2 h / 0 °C

1.2: 66 percent / CuSO₄*5H₂O / ethanol / 2 h / Heating

2.1: SnCl₂*2H₂O; NaBH₄ / ethanol / 0.33 h / Heating

With sodium tetrahydroborate; sulfuric acid; tin(ll) chloride; sodium nitrite; In ethanol;

DOI:10.1021/ol048820u

Reference yield:

4-nitro-aniline (100-01-6,104810-17-5) → 3,5-diiodoaniline (35122-96-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 74 percent / ICl / acetic acid / Heating

2.1: NaNO₂; aq. H₂SO₄ / 2 h / 0 °C

2.2: 3.2 g / CuSO₄*5H₂O; EtOH / Heating

3.1: 68 percent / H₂ / Raney Ni / ethanol / 4 h / 15 °C / 750.06 Torr

With sulfuric acid; hydrogen; Iodine monochloride; sodium nitrite; nickel; In ethanol; acetic acid;

DOI:10.1016/S0040-4020(02)00248-X

upstream raw materials:

3,5-diiodonitrobenzene

1,2,3-triiodo-5-nitrobenzene

2,6-diiodo-4-nitroaniline

4-nitro-aniline

Downstream raw materials:

N,N-diethyl-3,5-bis(ethynyl)aniline

N,N-diethyl-3,5-bis(trimethylsilylethynyl)aniline

3,5-bis(ethynyl)-N,N-dihexylaniline

N,N-dihexyl-3,5-bis(trimethylsilylethynyl)aniline

Refernces

Synthesis and optical properties of 6-substituted-β-cyclodextrin derivatives

10.2174/157017809790442899

The research aims to explore the synthesis and optical properties of α-cyclodextrin derivatives with varying lengths of π-conjugated arms. The study synthesizes three α-CD derivatives (compounds 4, 5, and 6) using key chemicals such as 6-deoxy-6-formyl-α-cyclodextrin, 3,5-diiodoaniline, and ethynylbenzene, among others. The structures of these compounds are confirmed through various analytical techniques including 1H NMR, elemental analysis, mass spectrometry, and X-ray crystal structure determination. The research evaluates their self-inclusion properties using Circular Dichroism and 1D and 2D 1H NMR measurements. The study concludes that as the length of the π-conjugated arm increases from 4 to 5 and to 6, the self-inclusion of the π-conjugated arm to the CD ring is enhanced, which in turn leads to stronger excitation-energy transfer in aqueous solutions. This finding suggests that self-inclusion of an aryl system into a CD cavity can significantly improve their optical properties, potentially offering new insights for applications in areas such as drug delivery systems and chemical sensors.