61982-94-3

Basic information

• Product Name: 1-Hydroxy-5-phenylnaphthalene
• Synonyms: 1-Hydroxy-5-phenylnaphthalene
• CAS NO: 61982-94-3
• Molecular Formula: C₁₆H₁₂O
• Molecular Weight: 220.26588
• Mol File: 61982-94-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 93-94 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• Boiling Point: 394.6±11.0 °C(Predicted)
• Appearance: /
• Density: 1.176±0.06 g/cm3(Predicted)
• PKA: 9.34±0.40(Predicted)
• CAS DataBase Reference: 1-Hydroxy-5-phenylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-5-phenylnaphthalene(61982-94-3)
• EPA Substance Registry System: 1-Hydroxy-5-phenylnaphthalene(61982-94-3)

Safety Data

• Hazardous Substances Data: 61982-94-3(Hazardous Substances Data)

Usage

Chemical Family

Polycyclic aromatic hydrocarbons (naphthalenes)

Physical Appearance

White to pale yellow crystalline substance

Primary Use

Intermediate in the production of dyes and pigments

Chemical Structure

Aromatic structure with a hydroxy group

Safety Precautions

Can cause skin and eye irritation; harmful if ingested or inhaled

Upstream product

• 242792-95-6 7-phenylindoline-2,3-dione 
• 74924-95-1 1-bromo-5-methoxynaphthalene 
• 61982-86-3 1-methoxy-5-phenylnaphthalene 
• 98-80-6 phenylboronic acid 
• 136131-40-3 5-phenyl-1,4-dihydro-1,4-epoxynaphthalene 
• 4445-39-0 2-amino-3-phenylbenzoic acid 
• 728-70-1 α-oximino-2-phenylacetanilide 

Downstream Products

• 62784-45-6 5-phenyl-[1,2]naphthoquinone 
• 1400967-97-6 C₁₆H₁₁⁽²⁾HO 

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.