Dinaphtho[2,3-b:2',3'-d]furan

Base Information

• Chemical Name: Dinaphtho[2,3-b:2',3'-d]furan
• CAS No.: 242-51-3
• Molecular Formula: C20H12O
• Molecular Weight: 268.31
• Hs Code.: 2932999099
• NSC Number: 167430
• DSSTox Substance ID: DTXSID90304807
• Nikkaji Number: J2.533.825A
• Wikidata: Q82051028
• Mol file: 242-51-3.mol

Synonyms:dinaphtho[2,3-b:2',3'-d]furan;242-51-3;Dinaphtho[2,3-b;12-oxapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,13,15,17,19-decaene;NSC167430;SCHEMBL903595;DTXSID90304807;NSC-167430;AS-56607;D93401

Chemical Property of Dinaphtho[2,3-b:2',3'-d]furan

Chemical Property:

• Melting Point: 266 °C (sublm)(Solv: benzene (71-43-2))
• Boiling Point: 486.9 °C at 760 mmHg
• Flash Point: 271.6 °C
• PSA: 13.14000
• Density: 1.285 g/cm³
• LogP: 5.89240
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 268.088815002
• Heavy Atom Count: 21
• Complexity: 355

Purity/Quality:

99% ^*data from raw suppliers

DINAPHTHO[2,3-B:2',3'-D]FURAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C3C(=CC2=C1)C4=CC5=CC=CC=C5C=C4O3

Technology Process of Dinaphtho[2,3-b:2',3'-d]furan

There total 7 articles about Dinaphtho[2,3-b:2',3'-d]furan 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: 96.0%

[2,2'-binaphthalene]-3,3'-diol (125663-74-3) → dinaphtho[2,3-b:2′,3′-d]furan (242-51-3)

Guidance literature:

With Zeolite HSZ-360; In 1,2-dichloro-benzene; at 160 ℃; for 16h; Inert atmosphere;

DOI:10.1246/bcsj.20170030

Reference yield:

5,6,7,8,5',6',7',8'-octahydro-[2,2']binaphthyl-3,3'-diyldiamine (114164-69-1) → dinaphtho[2,3-b:2′,3′-d]furan (242-51-3)

Guidance literature:

With hydrogenchloride; sodium nitrate; potassium iodide; Erhitzen des erhaltenen Jodoniumjodids mit Kupfer(I)-oxid unter vermindertem Druck auf 350grad;

DOI:10.1039/jr9590001670

Reference yield:

3-nitronaphthalen-2-amine (13115-28-1) → dinaphtho[2,3-b:2′,3′-d]furan (242-51-3)

Guidance literature:

Multi-step reaction with 4 steps

1: NaNO₂; H₂SO₄; acetic acid / anschliessendes Behandeln mit wss. KI

2: copper-powder / 130 - 135 °C

3: Raney nickel; acetic acid; ethanol / Hydrogenation

4: aqueous hydrochloric acid; sodium nitrate; potassium iodide / Erhitzen des erhaltenen Jodoniumjodids mit Kupfer(I)-oxid unter vermindertem Druck auf 350grad

With hydrogenchloride; sodium nitrate; ethanol; sulfuric acid; nickel; copper; acetic acid; potassium iodide; sodium nitrite;

DOI:10.1039/jr9590001670

upstream raw materials:

5,6,7,8,5',6',7',8'-octahydro-[2,2']binaphthyl-3,3'-diyldiamine

3-nitronaphthalen-2-amine

2-iodo-3-nitronaphthalene

3,3'-dinitro-[2,2']binaphthyl

Downstream raw materials:

6,7-Benzopentaphen

Refernces

• 1、 Kurata, Yuto,Otsuka, Shinya,Fukui, Norihito,Nogi, Keisuke,Yorimitsu, Hideki,Osuka, Atsuhiro. "Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C-O Arylation". supporting information. p. 1274 - 1277. Retrieved 2017/03/22.