196-78-1

Basic information

• Product Name: BENZO[G]CHRYSENE
• Synonyms: 1,2,3,4-dibenzophenanthrene;1,2,3,4-dibenzphenanthrene;1,2:3,4:7,8-tribenznaphthalene;BENZO[G]CHRYSENE;C100422;Benzo[a]triphenylene
• CAS NO: 196-78-1
• Molecular Formula: C₂₂H₁₄
• Molecular Weight: 278.35
• Mol File: 196-78-1.mol

Chemical Properties

• Melting Point: 126-127℃
• Boiling Point: 525℃
• Flash Point: 265℃
• Appearance: /
• Density: 1.232
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Refractive Index: 1.8120 (estimate)
• CAS DataBase Reference: BENZO[G]CHRYSENE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO[G]CHRYSENE(196-78-1)
• EPA Substance Registry System: BENZO[G]CHRYSENE(196-78-1)

Safety Data

• Hazardous Substances Data: 196-78-1(Hazardous Substances Data)

Usage

Safety Profile

Questionable carcinogen withexperimental tumorigenic data. When heated todecomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C22H14/c1-2-8-16-15(7-1)13-14-21-19-11-4-3-9-17(19)18-10-5-6-12-20(18)22(16)21/h1-14H

Upstream product

• 189999-35-7 [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate 
• 93-09-4 naphthalene-2-carboxylate 
• 132-64-9 dibenzofuran 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 17181-04-3 cis-1-phenyl-2-(9-phenanthryl)ethene 
• 6709-40-6 benzo[c]phenanthrene-5,6-dicarboxylic acid-anhydride 
• 71-43-2 benzene 
• 106-99-0 buta-1,3-diene 

Downstream Products

• 122048-50-4 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (9R,10R)-10-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-9,10-dihydro-benzo[g]chrysen-9-yl ester 
• 122048-50-4 ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (9S,10S)-10-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-9,10-dihydro-benzo[g]chrysen-9-yl ester 
• 122048-55-9 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (9R,10R)-10-bromo-9,10-dihydro-benzo[g]chrysen-9-yl ester 
• 122048-55-9 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (9S,10S)-10-bromo-9,10-dihydro-benzo[g]chrysen-9-yl ester 
• 84850-16-8 C₂₂H₁₄O 
• 84850-16-8 C₂₂H₁₄O 
• 84850-16-8 1a,13c-Dihydrobenzo<11,12>chryseno<5,6-b>oxirene 
• 132335-19-4 10-Phenylphenanthrene-2',9-dicarboxaldehyde 

Relevant articles and documents

Two-in-One Strategy for the Pd(II)-Catalyzed Tandem C-H Arylation/Decarboxylative Annulation Involved with Cyclic Diaryliodonium Salts

We report here a two-in-one strategy for the Pd(II)-catalyzed tandem C-H arylation/decarboxylative annulation between readily available cyclic diaryliodonium salts and benzoic acids. The carboxylic acid functionality can be used as both a directing group for the ortho-C-H arylation and the reactive group for the tandem decarboxylative annulation. By a step-economical double cross-coupling annulation procedure, the privileged triphenylene frameworks were efficiently constructed, which have potential applications in material chemistry.

Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C-O Arylation

A new class of aromatic metamorphosis has been developed in which dibenzofurans were converted into triphenylenes. This transformation is composed of three successive operations: (1) nickel-catalyzed ring-opening C-O bond arylation with arylmagnesium bromides, (2) trifluoromethanesulfonylation (triflation) of the resulting hydroxy moiety with Tf2O, and (3) palladium-catalyzed or photoinduced ring closure. In the last ring-closing step, the photoinduced process has proven to be more productive than the palladium-catalyzed one. By employing π-extended dinaphthofuran as the substrate, dorsally benzo-fused [5]helicene was obtained in a satisfactory yield.

Palladium-Assisted "Aromatic Metamorphosis" of Dibenzothiophenes into Triphenylenes

Abstract Two new palladium-catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3) an intramolecular SN2 reaction to form a teraryl sulfonium salt, and 4) palladium-catalyzed intramolecular C-S/C-H coupling through electrophilic palladation. Symmetrical as well as unsymmetrical triphenylenes of interest were synthesized in a tailor-made fashion in satisfactory overall yields. A change of heart: The invention of two palladium-catalyzed arylation reactions of organosulfur compounds enabled the transformation of dibenzothiophenes into triphenylenes and thus a fundamental change in the core aromatic structure (see scheme). Both symmetrical and unsymmetrical triphenylenes were synthesized in a tailor-made fashion in satisfactory overall yield.

Functionalized Enantiomerically Pure -, -, -, and Triblattanes

The methylene (2, 7, 10) and spirocyclopropane derivatives (8, 11, 12) are made accessible from rac-trishomocubane(mono-, di-, tri-)ones and optically pure unsaturated and benzoannulated - (19, 48), - (30, 53), and D3-symmetrical triblattanes (3, 4) from the enantiomers of these ketones by expeditious (one pot) ring enlargement and olefination procedures.In the case of the central trienes (+)-3/(-)-3, novel members of the (CH)14 family, optical resolution is advantageously postponed to the stage of the intermediate triones (35, 41) and effected via their (R,R)-2,3-butanediol acetals.In the α-diketone series only the dione (70) is sufficiently stable to allow isolation; tetrone 73 and hexone 5 are indirectly identified as quinoxalines 74 and 76; respectively.Tribenzotriblattane (-)-4 is established as the M-helical enantiomer by X-ray crystallography.Generally the thermal stabilization pathway of unsaturated and benzoannulated triblattanes is a cycloreversion with the primary cycloreversion products 2,7>tetradeca-3,5,9,11,13-pentane (78) from rac-3> being unstable under the drastic reaction conditions required.The stereochemical course of the perepoxidation of rac-3 is investigated. - Key Words: Trishomocubanes/ Spirocyclopropanes/ -, -, -, Triblattanes

Photochemical and Photophysical Behaviour of 9-Styrylphenanthrene and its Aza-Analogues

The photochemical and photophysical behaviour of 9-styrylphenanthrene and its pyridyl analogues, the 9-phenanthryl, n-pyridyl-ethylenes (n = 2,3,4), were studied in n-hexane and acetonitrile-water.Fluorescence spectra, quantum yields and lifetimes and trans --> cis photoisomerization quantum yields were determined for the trans isomers.The cis --> trans photoisomerization and dehydrophotocyclization quantum yields were measured for the cis isomers.The photocyclization products were isolated and characterized.The results obtained give a general picture of the competition among the various deactivating processes in these compounds.Mechanistic information is obtained also by comparison with what was found for other stilbene - like molecules. . - keyword: Styrylphenanthrenes and aza-analogues / Photoisomerization / Photocyclization / Fluorescence parameters

The formation and reactions of 9,10-phenanthryne and related arynes by pyrolytic reactions in the vapor phase

The formation of 9,10-phenanthryne (5), 4-methyl-9,10-phenanthryne (7) and 9,10-benz(c)phenanthryne (9) by the thermal degradation of appropriate arenedicarboxylic acid anhydrides has been investigated by a combination of VLPP and mass spectrometry and by a co-pyrolysis of the anhydrides with benzene, hexadeuterobenzene and 1,3-butadiene. Compounds 5,7 and especially 9 are formed easily by VLPP at 700-900° from the anhydrides. The results indicate that 7 and 9 are less reactive by H-addition to the aryne bond than 5, benzyne or naphthalyne, respectively. The results of the co-pyrolysis experiments show that 5 and 9 react with benzene and 1,3-butadiene by H-abstraction and addition reactions, similar to 1,2-benzyne and 2,3-naphthalyne. However, the reactivity of the aryne in the H-abstraction reaction decreases and the selectivity for the addition reaction increases in the series 1,2-benzyne, 2,3-naphthalyne, 9,10-phenanthryne and 9,10benz(c)phenanthryne.