1400967-84-1

Basic information

• Product Name: 5a,6-dihydrobenzo[d]naphtho[2,3-b]furan
• Synonyms: 5a,6-dihydrobenzo[d]naphtho[2,3-b]furan
• CAS NO: 1400967-84-1
• Molecular Weight: 220.271
• Mol File: 1400967-84-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5a,6-dihydrobenzo[d]naphtho[2,3-b]furan(CAS DataBase Reference)
• NIST Chemistry Reference: 5a,6-dihydrobenzo[d]naphtho[2,3-b]furan(1400967-84-1)
• EPA Substance Registry System: 5a,6-dihydrobenzo[d]naphtho[2,3-b]furan(1400967-84-1)

Safety Data

• Hazardous Substances Data: 1400967-84-1(Hazardous Substances Data)

Upstream product

• 580-13-2 2-bromonaphthalene 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 93321-12-1 2-(2'-methoxyphenyl)naphthalene 
• 67-56-1 methanol 
• 78210-35-2 2-(2-hydroxyphenyl)naphthalene 

Relevant articles and documents

Excited state intramolecular proton transfer (ESIPT) from phenol to carbon in selected phenylnaphthols and naphthylphenols

ESIPT and solvent-assisted ESPT in isomeric phenyl naphthols and naphthyl phenols 5-8 were investigated by preparative photolyses in CH 3CN-D2O, fluorescence spectroscopy, LFP, and ab initio calculations. ESIPT takes place only in 5 (D-exchange Φ = 0.3), whereas 6-8 undergo solvent-assisted PT with much lower efficiencies. The efficiency of the ESIPT and solvent-assisted PT is mainly determined by different populations of the reactive conformers in the ground state and the NEER principle. The D-exchange experiments and calculations using RI-CC2/cc-pVDZ show that 5 in S1 deactivates by direct ESIPT from the OH to the naphthalene position 1 through a conical intersection with S0, delivering QM 14 that was detected by LFP (τ = 26 ± 3 ns). ESIPT to position 3 in 5 is possible but it proceeds from a less-populated conformer and involves an energy barrier on S1. In solvent-assisted PT to naphthalene position 4 in 5, zwitterion 17 is formed, which cyclizes to stable naphthofuran photoproducts 9-12. The regiochemistry of the deuteration in solvent-assisted PT was correlated with the NBO charges of the corresponding phenolates/naphtholates 5--8-. Combined experimental and theoretical data indicate that solvent-assisted PT takes place via a sequential mechanism involving first deprotonation of the phenol/naphthol, followed by the protonation by H 2O in the S1 state of phenolate/naphtholate. The site of protonation by H2O is mostly at the naphthalene α-position.