194-63-8

Basic information

• Product Name: DINAPHTHO[1,2-B:1',2'-D]FURAN
• Synonyms: DINAPHTHO[2,1-B:1',2'-D]FURAN;DINAPHTHO[1,2-B:1',2'-D]FURAN;Nsc507496;dinaphtho[2,1-b:1',2'-d]furanChemical Formula: C20H12O Exact Mass: 268.09 Molecular Weight: 268.31 m/z: 268.09 (100.0%), 269.09 (21.7%), 270.10 (2.3%);1',2'-D]FURAN;DINAPHTHO[1,2-B
• CAS NO: 194-63-8
• Molecular Formula: C₂₀H₁₂O
• Molecular Weight: 268.31
• Mol File: 194-63-8.mol
• Article Data: 24

Chemical Properties

• Melting Point: 159 °C
• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: DINAPHTHO[1,2-B:1',2'-D]FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: DINAPHTHO[1,2-B:1',2'-D]FURAN(194-63-8)
• EPA Substance Registry System: DINAPHTHO[1,2-B:1',2'-D]FURAN(194-63-8)

Safety Data

• Hazardous Substances Data: 194-63-8(Hazardous Substances Data)

Usage

Uses

Dinaphtho[2,1-b:1'',2''-d]furan can induce aryl hydrocarbon receptor-mediated and estrogen receptor-mediated activities. It can also modulate cell proliferation.

Upstream product

• 573-97-7 1-bromo-2-naphthol 
• 602-09-5 1,1'-bi-2-naphthol 
• 135-76-2 sodium 2-naphthol-6-sulfonate 
• 135-19-3 β-naphthol 
• 108-95-2 phenol 
• 10034-85-2 hydrogen iodide 
• 86119-84-8 phosphoric acid 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 7732-18-5 water 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 65283-60-5 (R)-6,6'-dibromo-1,1'-binaphth-2-ol 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 
• 612-55-5 2-iodonaphthalene 

Downstream Products

• 88-99-3 benzene-1,2-dicarboxylic acid 
• 908350-73-2 2-(dicyclohexylphosphino)-2'-methoxy-1,1'-binaphthyl 
• 908293-77-6 2-(dicyclohexylphosphinoyl)-2'-methoxy-1,1'-binaphthyl 
• 857256-51-0 2'-(dicyclohexyl-phosphinoyl)-[1,1']binaphthalenyl-2-ol 
• 679787-78-1 2-(dicyclohexylphosphinoyl)-2'-isopropoxy-1,1'-binaphthyl 
• 679787-80-5 2-(dicyclohexylphosphinoyl)-2'-(benzyloxy)-1,1'-binaphthyl 

Relevant articles and documents

Oligonaphthofurans: Fan-shaped and three-dimensional π-compounds

Using a bottom-up method, we prepared a series of oligonaphthofurans composed of alternating naphthalene rings and furan rings. The largest compound (compound 25) contained 8 naphthalene units and 7 furan units. DFT calculations revealed that these compounds were fan-shaped molecules and each naphthalene ring was oriented in an alternate mountain-valley fold conformation because of steric repulsion by the hydrogens at the peri-positions. We investigated the optical properties that derived from their fan-shaped and mountain-valley sequences. As the number of aromatic rings of the oligonaphthofurans increased, the peaks of the longest wavelength absorptions in the UV-vis spectra (HOMO-LUMO energy gap) of these compounds steadily red-shifted, although the shapes of spectra were not sustained because of the decreasing molar absorption coefficients (εs) of their λmax. We compared our results with those reported for other types of oligoaromatic compounds such as acenes 1, ethene-bridged p-phenylenes 2, rylenes 3, oligofurans 4, and oligonaphthalenes 5. The slopes of the plots between the transition energies (HOMO-LUMO energy gap) of the oligoaromatic compounds and the reciprocal of the number of aromatic rings indicated that the efficiency of π conjugation of the oligonaphthofurans was comparable with that of linear and rigid acenes and rylenes. The higher-order compounds 22 and 25 aggregated even under high dilution conditions (～10-6 M).

Enantio- A nd Substrate-Selective Recognition of Chiral Neurotransmitters with C3-Symmetric Switchable Receptors

We report on the synthesis of C3-symmetric enantiopure cage molecules 1, which exhibit remarkable to exclusive enantioselective recognition properties toward chiral ammonium neurotransmitters. Strong changes in the substrate selectivity are als

Chiral Memory in Silylium Ions

The configurational stability of the chiral silicon center in Lewis base-stabilized silyliums has been studied. Complete retention of configuration at silicon is observed at low temperature in silylium ions stabilized by lone-pair interactions. In contras

Nickel-Catalyzed Enantioselective Arylative Activation of Aromatic C-O Bond

The pioneering nickel-catalyzed cross-coupling of C-O electrophiles was unlocked by Wenkert in the 1970s; however, the transition-metal-catalyzed asymmetric activation of aromatic C-O bonds has never been reported. Herein the first enantioselective activation of an aromatic C-O bond is demonstrated via the catalytic arylative ring-opening cross-coupling of diarylfurans. This transformation is facilitated via nickel catalysis in the presence of chiral N-heterocyclic carbene ligands, and chiral 2-aryl-2′-hydroxy-1,1′-binaphthyl (ArOBIN) skeletons are delivered axially in high yields with high ee. Moreover, this versatile skeleton can be transformed into various synthetic useful intermediates, chiral catalysts, and ligands by using the CH- and OH-based modifiable sites. This chemistry features mild conditions and good atom economy.

Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study

Experiments show that 1,1′-bi-2-naphthol (BINOL) undergoes facile C1-C1′ bond cleavage under action of triflic acid at temperatures above 0 °C to give mainly 2-naphthol along with oligomeric material. CASSCF and MRMP//CASSCF computations have demonstrated unambiguously that this unusual mode of scission of the biaryl bond can occur in the C1,C1′-diprotonated form of BINOL via a mechanism involving homolytic cleavage prompted by the intramolecular electrostatic repulsion. These findings also provide insights into the mechanism of a comparatively easy thermal cleavage of BINOL, implying the intermediacy of its neutral diketo form.