59115-49-0

Basic information

• Product Name: Naphthalene, 2-p-tolyl- (6CI,7CI)
• Synonyms: Naphthalene, 2-p-tolyl- (6CI,7CI);2-(4-Methylphenyl)naphthalene;2-p-Tolylnaphthalene
• CAS NO: 59115-49-0
• Molecular Formula: C₁₇H₁₄
• Molecular Weight: 218.29306
• Mol File: 59115-49-0.mol
• Article Data: 104

Chemical Properties

• Melting Point: 96-97℃
• Appearance: /
• CAS DataBase Reference: Naphthalene, 2-p-tolyl- (6CI,7CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 2-p-tolyl- (6CI,7CI)(59115-49-0)
• EPA Substance Registry System: Naphthalene, 2-p-tolyl- (6CI,7CI)(59115-49-0)

Safety Data

• Hazardous Substances Data: 59115-49-0(Hazardous Substances Data)

Usage

General Description

Naphthalene, 2-p-tolyl- (6CI,7CI) is a chemical compound with the molecular formula C16H12. It is a derivative of naphthalene, which is commonly used in mothballs, pesticides, and various industrial processes. The 2-p-tolyl- substitution indicates the presence of a tolyl group (Tol) at the 2 position of the naphthalene ring. This chemical is primarily used as an intermediate in the synthesis of other organic compounds. It is important to handle and store this chemical with caution, as it can be toxic and harmful if not used properly.

Upstream product

• 59115-35-4 8-methyl-7,8,9,10-tetrahydro-dibenzo[c,h]chromen-6-one 
• 624-31-7 4-tolyl iodide 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 580-13-2 2-bromonaphthalene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 106-38-7 para-bromotoluene 
• 32316-92-0 naphthalene-2-boronic acid 
• 2471-91-2 1,3-dihydrobenzo[c]thiophene-2,2-dioxide 
• 589-92-4 1-methylcyclohexan-4-one 
• 3857-83-8 2-naphthyl triflate 
• 5142-75-6 tri(p-tolyl)bismuth 
• 7385-85-5 naphthalen-2-yl tosylate 
• 17873-01-7 (4-methylphenyl)trimethoxysilane 
• 1523-11-1 naphthalen-2-yl acetate 

Relevant articles and documents

C(sp2)-C(sp2) cross coupling reaction catalyzed by a water-stable palladium complex supported onto nanomagnetite particles

A water-stable palladium complex supported onto nanomagnetite particles was prepared and characterized. The nanocatalyst showed excellent reusability and activity in aqueous phase processes including the C(sp2)-C(sp2) cross coupling reactions. The advantages of the protocol are its generality, high yields, short reaction time, a cleaner reaction profile, and simplicity.

Impact of Solvent and Their Contaminants on Pd/C Catalyzed Suzuki-Miyaura Cross-Coupling Reactions

The aim of this work was to understand if solvent contaminants can interfere in Suzuki’s cross-coupling reactions and if it can explain the lack of robustness in industrial processes. For this purpose, several parameters were tested on the industrial model reaction between 2-bromonaphthalene and phenylboronic acid catalyzed by Pd/C. Best results were obtained using THF as solvent. Traces of the precursors of the used solvents, such as 2,3-dihydrofurane or maleic anhydride (100–300 ppm related to the solvent) strongly poisoned the reaction, decreasing the conversion significantly. This means that to ensure robust production, solvent quality must be analyzed at the ppm level. Fortunately, addition of triphenylphosphine can circumvent the catalyst poisoning.

Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings

Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

Cobalt-Catalyzed Coupling of Aryl Chlorides with Aryl Boron Esters Activated by Alkoxides

The cobalt-catalyzed Suzuki biaryl cross-coupling of aryl chloride substrates with aryl boron reagents, activated with more commonly used bases, remained a significant unmet challenge in the race to replace platinum group metal catalysts with Earth-abundant metal alternatives. We now show that this highly desirable process can be realized using alkoxide bases, provided the right counterion is employed, strict stoichiometric control of the base is maintained with respect to the aryl boron reagent, and the correct boron ester is selected. Potassium tert-butoxide works well, but any excess of the base first inhibits and then poisons the catalyst. Lithium tert-butoxide performs very poorly, while even catalytic amounts of lithium additives also poison the catalyst. Meanwhile, a neopentane diol-based boron ester is required for best performance. As well as delivering this sought-after transformation, we have undertaken detailed mechanistic and computational investigations to probe the possible mechanism of the reaction and help explain the unexpected experimental observations.