2-Iodoaniline

Base Information

• Chemical Name: 2-Iodoaniline
• CAS No.: 615-43-0
• Deprecated CAS: 1619933-03-7
• Molecular Formula: C6H6IN
• Molecular Weight: 219.025
• Hs Code.: 29214210
• European Community (EC) Number: 210-426-0
• NSC Number: 34544
• DSSTox Substance ID: DTXSID5060649
• Nikkaji Number: J96.171J
• Wikidata: Q72483327
• Mol file: 615-43-0.mol

Synonyms:2-iodoaniline;2-iodobenzenamine

Chemical Property of 2-Iodoaniline

Chemical Property:

• Appearance/Colour: yellow to brown crystalline needles
• Vapor Pressure: 0.0112mmHg at 25°C
• Melting Point: 55-58 °C(lit.)
• Refractive Index: 1.688
• Boiling Point: 262 °C at 760 mmHg
• PKA: 2.6(at 25℃)
• Flash Point: 112.3 °C
• PSA: 26.02000
• Density: 1.924 g/cm³
• LogP: 2.45460
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 218.95450
• Heavy Atom Count: 8
• Complexity: 74.9

Purity/Quality:

99% ^*data from raw suppliers

2-Iodoaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-37/38-36/37/38
• Safety Statements: 36/37-36/37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)N)I
• Uses: 2-Iodobenzenamine is an synthetic intermediate for the synthesis of complex organic compounds and pharmaceuticals. 2-Iodoaniline is used as an intermediate in organic synthesis.

Technology Process of 2-Iodoaniline

There total 47 articles about 2-Iodoaniline 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: 99.2%

o-nitroiodobenzene (609-73-4) → 2-iodophenylamine (615-43-0)

Guidance literature:

With hydrogenchloride; iron; In water; N,N-dimethyl-formamide; for 2h; Reflux;

Reference yield: 98.0%

2-iodophenyl hydroxamic acid (79271-23-1) → 2-iodophenylamine (615-43-0)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 90 ℃; for 2h;

DOI:10.1039/b822806j

Reference yield: 98.0%

tert-butyl 2-iodophenylcarbamate (161117-84-6) → 2-iodophenylamine (615-43-0)

Guidance literature:

In 2,2,2-trifluoroethanol; at 150 ℃; for 1h; microwave irradiation;

DOI:10.1080/00397910802238718

upstream raw materials:

o-nitroiodobenzene

2-nitro-aniline

propan-1-ol

sodium n-propoxide

Downstream raw materials:

2-iodophenyl isothiocyanate

2'-hydroxyimino-2-iodoacetanilide

1-(2-iodophenyl)pyrrolidine-2,5-dione

N-(4-bromo-phenyl)-N'-(2-iodo-phenyl)-urea

Refernces

Copper-catalyzed annulation of 2-formylazoles with o-aminoiodoarenes

10.1021/jo9025644

The research focuses on the development of a copper-catalyzed annulation reaction between 2-formylazoles and o-aminoiodoarenes, leading to the synthesis of substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. This method provides a one-step route to these biologically active molecules, which are present in a growing number of pharmaceutical compounds. The reaction conditions were optimized using 2-iodoaniline and 2-formylpyrrole as starting materials, with the best results obtained using 1 equivalent of 2-formylpyrrole, 1.5 equivalents of 2-iodoaniline, 2 equivalents of K3PO4, 10 mol % CuI, 20 mol % sparteine, and NMP as the solvent at 130°C for 24 hours. The reaction was found to be effective for a variety of substituted aminoiodoarenes and formylazoles, including 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole. The synthesized products were analyzed using techniques such as high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS) to confirm their structures and purities.

Synthesis of 2-aryl-3-trifluoromethylquinolines using (E)-trimethyl(3,3,3- trifluoroprop-1-enyl)silane

10.1021/jo400859s

The study presents a novel synthetic method for the production of 2-aryl-3-trifluoromethylquinolines, which are compounds of interest in pharmaceutical, agrochemical, and high-performance material sectors due to their significant roles. The researchers utilized a Hiyama cross-coupling reaction involving (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane and 2-iodoaniline, facilitated by copper(II) fluoride and 2,2′-bipyridyl as a fluoride source and ligand, respectively. This reaction yielded (E)-2-(3,3,3-trifluoroprop-1-enyl)aniline without the need for amino group protection. Subsequently, an oxidative cyclization reaction with aryl aldehydes in the presence of a copper(I) salt catalyst, specifically [Cu(OTf)]2·C6H6, led to the formation of the target quinolines. The study's purpose was to develop an efficient synthetic protocol to access 3-trifluoromethylquinolines, which are challenging to synthesize using conventional methods, and to expand the library of such compounds for potential therapeutic applications.