9-Iodophenanthrene

Base Information

• Chemical Name: 9-Iodophenanthrene
• CAS No.: 17024-12-3
• Molecular Formula: C14H9 I
• Molecular Weight: 304.13
• Hs Code.: 2903999090
• European Community (EC) Number: 626-667-3
• NSC Number: 89105
• DSSTox Substance ID: DTXSID30293387
• Nikkaji Number: J618.874E
• Wikidata: Q82032088
• Mol file: 17024-12-3.mol

Synonyms:9-Iodophenanthrene;17024-12-3;Phenanthrene, 9-iodo-;9-phenanthryl iodide;9-iodophenanthren;NSC89105;9-Iodophenanthrene, 97%;NCIOpen2_009615;YSZC353;SCHEMBL942452;C14H9I;DTXSID30293387;MFCD00192230;NSC-89105;STK368376;AKOS005444386;DS-11798;CS-0098534;FT-0637473;A811182

Chemical Property of 9-Iodophenanthrene

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 1.38E-06mmHg at 25°C
• Melting Point: 91-93 °C(lit.)
• Boiling Point: 411°Cat760mmHg
• Flash Point: 186.6°C
• PSA: 0.00000
• Density: 1.692g/cm³
• LogP: 4.59760
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 303.97490
• Heavy Atom Count: 15
• Complexity: 225

Purity/Quality:

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

9-Iodophenanthrene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C3=CC=CC=C23)I

Technology Process of 9-Iodophenanthrene

There total 7 articles about 9-Iodophenanthrene 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: 85.0%

9-bromophenanthrene (573-17-1) → 9-iodo-phenanthrene (17024-12-3)

Guidance literature:

9-bromophenanthrene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

With iodine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1055/s-0033-1339892

Reference yield: 65.0%

2-(iodoethynyl)-1,1'-biphenyl (330565-89-4) → 9-iodo-phenanthrene (17024-12-3)

Guidance literature:

With aluminum oxide; In neat (no solvent, solid phase); at 90 ℃; for 6h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.1c07845

Reference yield:

1-phenyl-2-{2-(trimethylsilyl)ethynyl}benzene (147492-79-3) → 9-iodo-phenanthrene (17024-12-3)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / methanol / 20 °C

2: N-iodo-succinimide; silver nitrate / tetrahydrofuran / 3 h / 20 °C

3: aluminum oxide / neat (no solvent, solid phase) / 6 h / 90 °C / Schlenk technique; Inert atmosphere

With aluminum oxide; N-iodo-succinimide; potassium carbonate; silver nitrate; In tetrahydrofuran; methanol;

DOI:10.1021/jacs.1c07845

upstream raw materials:

9-phenanthrylmagnesium bromide

9-bromophenanthrene

1-phenyl-2-{2-(trimethylsilyl)ethynyl}benzene

2-(iodoethynyl)-1,1'-biphenyl

Downstream raw materials:

phenanthrene-9-carboxamide

9-acetylphenanthrene

9,10-phenanthrenequinone

phenanthrene

Refernces

• 1、 Goldberg,Ordas,Carsch. "". . p. 260,262. Retrieved 1947.
• 2、 Akhmetov, Vladimir,Amsharov, Konstantin,Feofanov, Mikhail,Sharapa, Dmitry I.. "Alumina-Mediated π-Activation of Alkynes". . p. 15420 - 15426. Retrieved 2021/09/30.
• 3、 Urselmann, Dominik,Antovic, Dragutin,Mueller, Thomas J. J.. "Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira-Glaser cyclization sequence". supporting information; experimental part. p. 1499 - 1503. Retrieved 2011/12/22.