573-57-9

Basic information

• Product Name: 1,4-EPOXY-1,4-DIHYDRONAPHTHALENE
• Synonyms: 1,4-Dihydronaphthalene-1,4-endo-oxide;1,4-Dihydronaphthalene-1,4-oxide;1,4-EPOXY-1,4-DIHYDRONAPHTHALENE;1,4-DIHYDRO-1,4-EPOXYNAPHTHALENE;7-OXABENZONORBORNADIENE;1,4-EPOXY-1,4-DIHYDRONAPHTHALENE 99%;1,4-Epoxynaphthalene,1,4-dihydro-;1,3-Etheno-1,3-dihydroisobenzofuran
• CAS NO: 573-57-9
• Molecular Formula: C₁₀H₈O
• Molecular Weight: 144.17
• Mol File: 573-57-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 241℃
• Flash Point: 93 °C
• Appearance: white to yellow crystalline solid
• Density: 1.207
• Vapor Pressure: 0.0587mmHg at 25°C
• Refractive Index: 1.5598 (estimate)
• CAS DataBase Reference: 1,4-EPOXY-1,4-DIHYDRONAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-EPOXY-1,4-DIHYDRONAPHTHALENE(573-57-9)
• EPA Substance Registry System: 1,4-EPOXY-1,4-DIHYDRONAPHTHALENE(573-57-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 573-57-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 43, p. 1599, 1965 DOI: 10.1139/v65-211Chemistry Letters, 12, p. 1211, 1983

Purification Methods

Dissolve it in Et2O, wash it with H2O, dry it over K2CO3, filter, evaporate and dry the residue at 15mm, then recrystallise it from pet ether (b 40-60o), dry it at 25o/0.005mm and sublime it (sublimes slowly at room temperature)[Wittig & Pohmer Chem Ber 89 1334 1956, Gilman & Gorsich J Am Chem Soc 79 2625 1957]. [Beilstein 17 III/IV 548.]

InChI:InChI=1/C10H8O/c1-2-4-8-7(3-1)9-5-6-10(8)11-9/h1-6,9-10H

Upstream product

• 110-00-9 furan 
• 126218-83-5 1-bromo-2-(methylsulfinyl)benzene 
• 925-90-6 ethylmagnesium bromide 
• 17051-75-1 o-chlorophenyl phenyl sulfoxide 
• 112921-53-6 ethyl (2-bromo)phenyl sulfoxide 
• 112921-52-5 o-bromophenyl phenyl sulfoxide 
• 67-56-1 methanol 
• 1608-42-0 benzenedizolium-2-carboxylate 
• 75-05-8 acetonitrile 
• 1027537-24-1 (4-tetradecylphenyl)[2-(trimethylsilyl)phenyl]iodonium triflate 
• 75802-19-6 1-Ethoxy-1,3-dihydroisobenzofuran 
• 591-50-4 iodobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 91-00-9 Benzhydrylamine 

Downstream Products

• 38648-86-1 phenyl-((3at,9at)-3a,4,9,9a-tetrahydro-4r,9c-epioxido-naphtho[2,3-d]isoxazol-3-yl)-methanone 
• 38648-94-1 1-phenyl-(3at,9at)-3a,4,9,9a-tetrahydro-1H-4r,9c-epioxido-naphtho[2,3-d][1,2,3]triazole 
• 104975-98-6 exo-1,4,4a,5,10,10a-Hexahydro-4-methyl-2,11-diphenyl-5,10-epoxy-1,4-(iminomethano)benzisochinolin-3(2H),12-dion 
• 104994-62-9 exo-1,4,4a,5,10,10a-Hexahydro-1,4-dimethyl-2,11-diphenyl-5,10-epoxy-1,4-(iminomethano)benzisochinolin-3(2H),12-dion 
• 493-04-9 isotetraline 
• 119-64-2 tetralin 
• 612-17-9 1,4-dihydronaphthalene 
• 13395-89-6 5,12-dihydro-5,12<1',2'>-benzenonaphthacene 
• 10344-58-8 2,3-Diphenyl-1,4-dodecamethylen-benzol 
• 503624-63-3 (1SR,2SR)-2-methyl-1,2-dihydronaphthalen-1-ol 
• 55240-76-1 1,8-Diphenyl-4,5:9,10-dibenzo-11,12-dioxa-4,9-tetracyclo<6.2.1.1^3.60^2,7>dodecadiene 
• 91-20-3 naphthalene 
• 90-15-3 α-naphthol 
• 37480-22-1 1-hydroxy-1,2-dihydronaphthalene 

Relevant articles and documents

Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions

A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodology is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required.

Improved solubility of hypervalent iodine-benzyne precursors: Synthesis and reaction of (phenyl)[2-(trimethylsilyl)phenyl]iodonium salts bearing long alkyl chains

Synthesis of new long-chained hypervalent iodine-benzyne precursors, (4-dodecylphenyl)[2-(trimethylsilyl)phenyl]iodonium triflate and the tetradecyl derivative, is described. The benzyne precursors dissolve even in organic solvents of low polarity such as diethyl ether, THF, cyclopentyl methyl ether, benzene, and toluene. The trapping reactions with furan and tetraphenylcy-clopentadienone in the above solvent give the benzyne adducts in high yields without any loss of high reactivity of hypervalent iodine-benzyne precursors.

Benzyne formation and the stepwise decomposition of benzenediazonium-2-carboxylate: A re-investigation

A study of the decomposition reactions of benzenediazonium-2-carboxylate, carried out in a number of mixed nucleophilic solvents, shows that a number of mechanistic pathways can operate simultaneously and can afford, in addition to products derived from benzyne, products derived from the 2-carboxyphenyl cation and the 2-carboxyphenyl radical: benzyne formation is favoured in halogenated solvents and occurs by the concerted loss of nitrogen and carbon dioxide.