60433-62-7

Usage

Physical state

White solid

Solubility

Sparingly soluble in water

Uses

Manufacturing of dyes and pigments, intermediate in organic synthesis, potential pharmaceutical applications

Antioxidant properties

Yes

Potential use as a photostabilizer

In plastics and other materials

Potential use in fluorescent dyes

Yes

Potential use as a photosensitizer

In photodynamic therapy for cancer treatment

Upstream product

• 3402-76-4 1-phenoxynaphthalene 
• 1623-99-0 phenyl sodium 
• 38666-59-0 mesityl 1-naphthyl ketone 
• 71-43-2 benzene 
• 90-15-3 α-naphthol 
• 3049-07-8 pentaphenylbismuth 
• 536-74-3 phenylacetylene 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 108-86-1 bromobenzene 
• 573-57-9 1,4-dihydronaphthalene-1,4-epoxide 
• 591-50-4 iodobenzene 
• 879-15-2 2-diazo-1,2-naphthoquinone 
• 98-80-6 phenylboronic acid 
• 591-51-5 phenyllithium 

Downstream Products

• 65-85-0 benzoic acid 
• 1402750-29-1 C₁₆H₁₀⁽²⁾H₂O 
• 1402750-28-0 C₁₆H₁₁⁽²⁾HO 
• 58665-28-4 2-phenyl-1-methoxynaphthalene 
• 612-94-2 2-phenylnaphthalene 
• 74886-78-5 3,3'-diphenyl-[1,1']binaphthylidene-4,4'-dione 

Relevant academic research and scientific papers

Pd-catalyzed ring opening of oxa- and azabicyclic alkenes with aryl and vinyl halides: Efficient entry to 2-substituted 1,2-dihydro-1-naphthols and 2-substituted 1-naphthols

An efficient syntheses of 2-substituted 1,2-dihydro-1-naphthols and 2-substituted 1-naphthols has been developed that involves the sequential palladium-catalyzed ring opening of oxabicyclic alkenes with aryl and vinyl halides followed by oxidation of with

Sulphonic acid functionalized porphyrin anchored with a: Meso -substituted triazolium ionic liquid moiety: A heterogeneous photo-catalyst for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation

We report an easy process to synthesize sulphonic acid functionalized porphyrin, anchored with a meso-substituted triazolium ionic liquid moiety (SAFPTILM) for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation. The acid strength has been measured based on the Hammett indicator. The SAFPTILM photocatalyst comprising 18 π-conjugated electronic systems with the chromophore substituents in the meso-position can provide rapid electronic conducting channels during photocatalysis under the irradiation of visible light. It was found that SAFPTILM is an efficient photocatalyst for the Heck, Sonogashira, Buchwald, Ullmann/Fittig coupling and C-H activation of phenols with different aryl chlorides in the absence of a base/noble metal, using 5 W LED (yellow) light under ambient conditions. The photocatalyst with low band gap (1.55 eV) comprising conjugation, favors coupling reaction of unactivated aryl chlorides, by easy excitation of electrons and transfer to the conjugated benzimidazolium based phenylenediamine support delaying the recombination of photoinduced electron-hole pairs.

Potassium tert-butoxide-mediated synthesis of unsymmetrical diaryl ethers, sulfides and selenides from aryl bromides

Potassium tert-butoxide mediated carbon-chalcogen C-E (E=O, S and Se) coupling reaction has been studied from aryl bromide and phenol/aryl disulfide/diselenide substrates. A series of unsymmetrical diaryl chalcogenides were accessed from aryl bromide and diaryl dichalcogenide precursors by using 2.5 equiv of potassium tert-butoxide in DMSO at 80 C. Unsymmetrical diaryl ethers were also obtained by using phenol precursors at 40-45 C. Aryl bromides with methyl, trifluoromethyl, methoxy and nitro substituents showed compatibility in the carbon-chalcogen bond forming reaction. 4-Methoxy, methyl, trifluoromethyl substituted bromobenzene substrates gave two regioisomers: 3-substituted and 4-substituted diaryl chalcogenides when reacted with phenols/diaryl disulfides/diselenides. Formation of two regioisomeric diaryl chalcogenides in the reaction mixture suggests that potassium tert-butoxide reacts with bromobenzene to produce benzyne intermediate, which subsequently reacts with diaryl dichalcogenides and finally give a regioisomeric mixture of 4-substituted and 3-substituted diaryl chalcogenides.

Divergent reaction pathways for phenol arylation by arynes: Synthesis of helicenes and 2-arylphenols

Two reactions of phenols with arynes have been developed. If LiTMP base is employed, arynes generated from aryl chlorides react with phenols to form helicenes. o-Arylation of phenols can be achieved by employing tBuONa base in the presence of AgOAc. Direc

P-directed borylation of phenols

Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf2 to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF2 to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf2 byproduct from the preceding KHF2 step.

Very efficient generation of quinone methides through excited state intramolecular proton transfer to a carbon atom

Irradiation of 2-phenyl-1-naphthol (6) in CH3CN/D2O (3:1) leads to very efficient incorporation of deuterium at the ortho-positions of the adjacent phenyl ring (overall φ=0.73±0.07), along with minor incorporation at the naphthalene positions 5 and 8. These finding are explained by excited state intramolecular proton transfer (ESIPT) from the phenolic OH group to the corresponding carbon atoms, the main pathway giving rise to quinone methide (QM) 7, which has been characterized by LFP (τ≈20 ns; 460 nm). The ESIPT reaction paths have been explored with the second order approximate coupled cluster (CC2) method. In nonprotic solvents the ESIPT from the naphthol O-H to the ortho-position of the phenyl ring proceeds in a barrierless manner along the 1La energy surface via a conical intersection with the S0 state, delivering 7. In aqueous solvent, clusters with H2O are formed wherein proton transfer (PT) to solvent and a H 2O-mediated relay mechanism gives rise to naphtholates and QMs. The results are compared with 2-phenylphenol (3) that also undergoes barrierless ESIPT giving a QM via a conical intersection. However, due to an unfavorable conformation in the ground state, the quantum efficiency for ESIPT of 3 is significantly lower (φ for D-exchange=0.041). These results show that ESIPT from phenol to carbon need not be an intrinsically inefficient process. Irradiation of 2-phenyl-1-naphthol in CH3CN/D2O (3:1) leads to very efficient incorporation of deuterium at the ortho-positions of the adjacent phenyl ring along with minor incorporation at the naphthalene positions 5 and 8. These findings are explained by excited state intramolecular proton transfer (ESIPT) from the phenol OH to the corresponding carbon atoms (see figure). Copyright

Synthesis of substituted α-tetralones and substituted 1-naphthols via regioselective ring expansion of 1-acyl-1-indanol skeleton

Substituted 1-acyl-1-indanols were prepared using the corresponding readily commercially available substituted indanones as starting materials. Treatment of each 1-acyl-1-indanol derivative with sodium methoxide in hot methanol furnished a regiospecific 2-hydroxy-α-tetralone derivative, which was an α-keto rearrangement product. Each substituted 2-hydroxy-α-tetralone then underwent dehydration to afford the corresponding 1-naphthol derivative.

Palladium-catalyzed cross-coupling reactions of 2-diazonaphthoquinones with arylboronic acids

Palladium-catalyzed cross-coupling reactions of 2-diazonaphthoquinones and arylboronic acids proceeded by the treatment with Pd(OAc)2 in acetic acid to afford 2-aryl-1-naphthols.

Benzannulation for the regiodefined synthesis of 2-alkyl/aryl-1-naphthols: Total synthesis of arnottin i

The annulation of phthalides with α-alkyl/arylacrylates in the presence of LDA/LHMDS is shown to directly give alkyl/aryl-1-naphthols. The method involving a novel dealkoxycarbonylation obviates the regiochemical issues in the synthesis of polysubstituted naphthalenes, and it forms the key step in a three-step total synthesis of arnottin I, a naphthobenzopyranone natural product.

Rhodium-HMPT-catalyzed direct ortho arylation of phenols with aryl bromides

Direct ortho arylation of phenols with aryl bromides catalyzed by a rhodium complex and hexamethylphosphorous triamide (HMPT) have been developed. A plausible reaction mechanism involving in situ generation of arylphosphites from phenols and HMPT, phosphorus-directed ortho metalation, and transesterification of the arylated arylphosphites with the substrate phenols is proposed.