200-23-7

Basic information

• Product Name: benzo(k l)xanthene
• Synonyms: benzo(k l)xanthene;Einecs 205-901-4
• CAS NO: 200-23-7
• Molecular Formula: C₁₆H₁₀O
• Molecular Weight: 234.29246
• EINECS: 205-901-4
• Mol File: 200-23-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 109 °C
• Boiling Point: 395.1°Cat760mmHg
• Flash Point: 191.2°C
• Appearance: /
• Density: 1.257g/cm³
• Vapor Pressure: 4.28E-06mmHg at 25°C
• Refractive Index: 1.721
• CAS DataBase Reference: benzo(k l)xanthene(CAS DataBase Reference)
• NIST Chemistry Reference: benzo(k l)xanthene(200-23-7)
• EPA Substance Registry System: benzo(k l)xanthene(200-23-7)

Safety Data

• Hazardous Substances Data: 200-23-7(Hazardous Substances Data)

Usage

General Description

Benzo(k l)xanthene is a polycyclic aromatic hydrocarbon with a unique structure containing four fused rings. It is a highly fluorescent compound that is often used as a tracer dye for measuring flow rates in hydrologic systems. Additionally, it has been studied for potential applications in organic light-emitting diodes and other optoelectronic devices due to its strong fluorescent properties. Benzo(k l)xanthene is considered hazardous and potentially carcinogenic, and caution should be exercised during its handling and use in laboratory and industrial settings.

InChI:InChI=1/C16H10O/c1-2-9-14-12(7-1)13-8-3-5-11-6-4-10-15(17-14)16(11)13/h1-10H

Upstream product

• 22591-15-7 2-(naphthalen-1-yl)cyclohexanone 
• 33718-15-9 1-bromo-8-fluoronaphthalene 
• 1993-03-9 o-fluorophenylboronic acid 
• 32219-16-2 1-(2-aminophenoxy)naphthalene 
• 32219-13-9 1-(2-nitrophenoxy)naphthalene 
• 88-73-3 2-Chloronitrobenzene 
• 90-15-3 α-naphthol 
• 1245937-16-9 1-naphthyl 2-(allyloxy)benzoate 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 408313-37-1 (+/-)-1-Hydroxy-1-(2-methoxy-phenyl)-1.2.3.4-tetrahydro-naphthalin 
• 116400-74-9 2-(3,4-dihydro-[1]naphthyl)-anisole 
• 93321-11-0 1-(2-methoxyphenyl)naphthalene 
• 101277-90-1 1-(2′-hydroxyphenyl)naphthalene 

Relevant articles and documents

Excited-state intramolecular proton transfer in o-hydroxybiaryls: A new route to dihydroaromatic compounds

An excited-state intramolecular proton transfer (ESIPT) from the phenol OH to the 7′-carbon on the naphthyl ring in o-(1-naphthyl)phenol (3) and 1-(1′-naphthyl)-2-naphthol (4) leads to efficient (Φ = 0.1-0.2) formation of the corresponding dihydrobenzoxanthenes (5 and 7) via quinone methide intermediates. This new reaction represents a clean, efficient, and high-yielding route to benzoxanthenes and dihydrobenzoxanthenes. A related ESIPT of similar efficiency has been detected at the 2′-aromatic position in these systems, by deuterium labeling studies. Copyright

NMR and DFT studies on persistent carbocations derived from benzo[kl]xanthene, dibenzo[d,d′]benzo[1,2-b:4,3-b′]difuran, and dibenzo[d,d′]benzo[1,2-b:4,5-b′]difuran in superacidic media

Persistent carbocations generated by the protonation of hetero-polycyclic aromatic compounds with oxygen atom(s) were studied by experimental NMR and density function theory calculations. Benzo[kl]xanthene (1), dibenzo[d,d′]benzo[1,2-b:4,3-b′]difuran (2), and dibenzo[d,d′]benzo[1,2-b:4,5-b′]difuran (3) were synthesized by the annulation of arenediazonium salts. Compound 1 in FSO3H-SbF5 (4:1)/SO2ClF and 3 in FSO3H-SbF5 (1:1)/SO2ClF ionized to 1aH+ with protonation at C(4) and to 3aH+ with protonation at C(6), and these cations were successfully observed by NMR at low temperatures. The density function theory calculations indicated that 1aH+ and 3aH+ were the most stable protonated carbocations and that 2 should ionize to 2aH+ with protonation at C(6). According to the changes in 13C chemical shifts (Δδ13C), the positive charge was delocalized into the naphthalene unit for 1aH+, into one benzo[b,d]furan unit for 2aH+, and into one benzo[b,d]furan unit for 3aH+. The most stable persistent cations derived from the title compounds, 1-3, were found to be 1aH+ with protonation at C(4), 2aH+ with protonation at C(6), and 3aH+ with protonation at C(6) by experimental and theoretical methods.

Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions

Flash vacuum pyrolysis (FVP) of aryl 2-(allyloxy)benzoates 5 and of the corresponding aryl 2-(allylthio)benzoates 6 at 650°C, gives dibenzofurans 19 and dibenzothiophenes 20, respectively. The mechanism involves generation of phenoxyl (or thiophenoxyl) radicals by homolysis of the O-allyl (or S-allyl) bond, followed by ipso attack at the ester group, loss of CO2 and cyclisation of the resulting aryl radical. Synthetically, the procedure works well for p-substituted substrates, which lead to 2-substituted dibenzofurans 19b-f (73-90%) and dibenzothiophenes 20b-c (90-94%). Little selectivity is shown in the cyclisation of m-substituted substrates and competing interactions of the radical with the substituent - and ipso-attack - complicate the pyrolyses of o-substituted substrates. FVP of related radical precursors including 2-(allyloxy)phenyl benzoates 43 gave no dibenzofurans, whereas 2-(allyloxy-5-methyl)azobenzene 44 gave a much reduced yield. No carbazoles were obtained by FVP of 4-methylphenyl 2-(allylamino)benzoate 42.