7-Tertbutyl-2-nitrofluorene

Base Information

• Chemical Name: 7-Tertbutyl-2-nitrofluorene
• CAS No.: 60758-15-8
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.327
• Hs Code.: 2904209090
• DSSTox Substance ID: DTXSID70483942
• Nikkaji Number: J1.158.683J
• Wikidata: Q82321822
• Mol file: 60758-15-8.mol

Synonyms:7-TERTBUTYL-2-NITROFLUORENE;60758-15-8;DTXSID70483942

Chemical Property of 7-Tertbutyl-2-nitrofluorene

Chemical Property:

• PSA: 45.82000
• LogP: 4.98670
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 267.125928785
• Heavy Atom Count: 20
• Complexity: 381

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC2=C(C=C1)C3=C(C2)C=C(C=C3)[N+](=O)[O-]

Technology Process of 7-Tertbutyl-2-nitrofluorene

There total 7 articles about 7-Tertbutyl-2-nitrofluorene 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: 72.0%

2-(4-tert-Butylphenyl)-5-nitrobenzyl alcohol (243122-80-7) → 7-tert-Butyl-2-nitrofluorene (60758-15-8)

Guidance literature:

With methanesulfonic acid; In chloroform; Heating;

DOI:10.1055/s-1999-3537

Reference yield: 30.0%

2,7-di-tert-butyl-9H-fluorene (58775-05-6) → 7-tert-Butyl-2-nitrofluorene (60758-15-8) + 2,7-di-t-butyl-4-nitrofluorene (91611-99-3)

Guidance literature:

With nitric acid; acetic acid; In acetic anhydride; at -20 - 0 ℃; for 2h;

DOI:10.1055/s-1984-30835

Reference yield:

methyl 2-bromo-5-nitrobenzoate (6942-36-5) → 7-tert-Butyl-2-nitrofluorene (60758-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

1.2: ZnCl₂ / tetrahydrofuran / 1 h

1.3: 73 percent / Pd(dba)2; dppf / tetrahydrofuran / 18 h / 20 °C

2.1: 99 percent / LiBH₄ / diethyl ether; methanol; tetrahydrofuran / 0 - 20 °C

3.1: 72 percent / PPA; MeSO₃H / CHCl₃ / Heating

With lithium borohydride; methanesulfonic acid; tert.-butyl lithium; In tetrahydrofuran; methanol; diethyl ether; chloroform; pentane; 1.1: Metallation / 1.2: Transmetallation / 1.3: Negishi coupling / 2.1: Reduction / 3.1: Cyclization;

DOI:10.1055/s-1999-3537

upstream raw materials:

2,7-di-tert-butyl-9H-fluorene

2-(4-tert-Butylphenyl)-5-nitrobenzyl alcohol

methyl 2-bromo-5-nitrobenzoate

Methyl 2-(4-tert-butylphenyl)-5-nitrobenzoate

Refernces

• 1、 Kajigaeshi, Shoji,Kadowaki, Toshiya,Nishida, Akiko,Fujisaki, Shizuo,Noguchi, Michihiko. "A Facile Synthesis of 4-Substituted Fluorenes by the Use of a Positional Protective Group". . p. 335 - 337. Retrieved 2007/10/02.