Triphenylene, 2-nitro-

Base Information

• Chemical Name: Triphenylene, 2-nitro-
• CAS No.: 81316-79-2
• Molecular Formula: C₁₈H₁₁NO₂
• Molecular Weight: 273.291
• DSSTox Substance ID: DTXSID30231047
• Nikkaji Number: J1.191.591D
• Wikidata: Q83111858
• ChEMBL ID: CHEMBL165094
• Mol file: 81316-79-2.mol

Synonyms:2-nitrotriphenylene;Triphenylene, 2-nitro-;81316-79-2;2-Nitro-triphenylene;SCHEMBL311661;CHEMBL165094;DTXSID30231047;WFWCWFPGYUDATP-UHFFFAOYSA-N

Chemical Property of Triphenylene, 2-nitro-

Chemical Property:

• Vapor Pressure: 3.37E-10mmHg at 25°C
• Boiling Point: 514.8°Cat760mmHg
• Flash Point: 258.8°C
• PSA: 45.82000
• Density: 1.342g/cm³
• LogP: 5.57760
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 273.078978594
• Heavy Atom Count: 21
• Complexity: 405

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=C(C=C(C=C3)[N+](=O)[O-])C4=CC=CC=C24

Technology Process of Triphenylene, 2-nitro-

There total 29 articles about Triphenylene, 2-nitro- 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: 92.0%

2-iodo-4’-nitrobiphenyl (2499-71-0) + 2-(2-bromophenyl)propanol (7073-69-0) → 2-nitrotriphenylene (81316-79-2)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; caesium carbonate; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; In toluene; at 110 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol4025869

Reference yield: 88.0%

diphenyl(trifluoromethanesulfonato)-λ3-iodane + 1-bromo-2-(4-nitrophenyl)benzene (80334-07-2) → 2-nitrotriphenylene (81316-79-2)

Guidance literature:

With cesium acetate; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 12h; Inert atmosphere; Schlenk technique;

Reference yield: 88.0%

1-bromo-2-(4-nitrophenyl)benzene (80334-07-2) + Diphenyliodonium triflate (66003-76-7) → 2-nitrotriphenylene (81316-79-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium acetate; sodium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 12h; Schlenk technique;

DOI:10.1021/acs.joc.7b01905

upstream raw materials:

triphenylene

2-iodo-4’-nitrobiphenyl

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

p-nitrobenzene iodide

Refernces

• 1、 Liu, Zhijian,Zhang, Xiaoxia,Larock, Richard C.. "Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls". . p. 15716 - 15717. Retrieved 2005.
• 2、 Tu, Jingxuan,Li, Gaoqiang,Zhao, Xiaoqian,Xu, Feng. "Synthesis of triphenylene derivatives by Pd-catalyzed Suzuki coupling/intramolecular C–H activation between arylboronic acids and dibromobiphenyls". supporting information. p. 44 - 47. Retrieved 2018/11/30.
• 3、 Wu, Xunshen,Han, Jianwei,Wang, Limin. "Palladium Catalyzed C-I and Vicinal C-H Dual Activation of Diaryliodonium Salts for Diarylations: Synthesis of Triphenylenes". . p. 49 - 56. Retrieved 2017/12/15.