7397-93-5

Usage

Uses

Used in Toxicological Studies:
6-Bromochrysene is used as a reference standard in toxicological studies for assessing the health risks associated with exposure to polycyclic aromatic hydrocarbons. Its mutagenic and carcinogenic properties make it a valuable tool in evaluating the effects of such compounds on human health.
Used in Research and Development:
Due to its mutagenic activity, 6-Bromochrysene is utilized in research and development for understanding the mechanisms of DNA damage and mutation induction. It aids in the development of strategies to mitigate the harmful effects of similar compounds.
Used in Environmental Monitoring:
6-Bromochrysene is also used in environmental monitoring to detect and quantify the presence of polycyclic aromatic hydrocarbons in various samples, such as air, water, and soil. This helps in assessing the environmental impact of these pollutants and implementing appropriate remediation measures.
It is crucial to handle 6-Bromochrysene with caution and adhere to safety protocols to minimize the risk of exposure, given its potential carcinogenic and mutagenic properties.

InChI:InChI=1/C18H11Br/c19-18-11-17-13-6-2-1-5-12(13)9-10-15(17)14-7-3-4-8-16(14)18/h1-11H

Synthetic route

chrysene (218-01-9) → 6-bromochrysene (7397-93-5)

Conditions	Yield
With N-Bromosuccinimide In water at 60℃; for 20h;	77%
With bromine; nitrobenzene at 120℃;
With tetrachloromethane; N-Bromosuccinimide

chrysene (218-01-9) + acetic acid (64-19-7) → 6-bromochrysene (7397-93-5) + trans-5-acetoxy-6-bromo-5,6-dihydrochrysene (89523-48-8, 105882-35-7)

Conditions	Yield
With N-bromoacetamide for 24h; Ambient temperature;	A n/a B 68%

trans-5-acetoxy-6-bromo-5,6-dihydrochrysene (89523-48-8, 105882-35-7) → 6-bromochrysene (7397-93-5)

Conditions	Yield
With trifluoroacetic acid

chrysene (218-01-9) + bromine (7726-95-6) → 6-bromochrysene (7397-93-5)

tetrachloromethane (56-23-5) + N-Bromosuccinimide (128-08-5) + chrysene (218-01-9) → 6-bromochrysene (7397-93-5)

N-Bromosuccinimide (128-08-5) + chrysene (218-01-9) + benzene (71-43-2) → 6-bromochrysene (7397-93-5)

Triphenylsilyl chloride (76-86-8) + 6-bromochrysene (7397-93-5) → C36H26Si

Conditions	Yield
Stage #1: 6-bromochrysene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: Triphenylsilyl chloride In tetrahydrofuran at 20℃; for 1h;	60%

6-bromochrysene (7397-93-5) + bis(pinacol)diborane (73183-34-3) → C24H23BO2 (875916-80-6)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100 - 110℃; for 2h; Inert atmosphere;	38%

6-bromochrysene (7397-93-5) + (2-bromophenyl)boronic acid (244205-40-1) → 6-(2-bromophenyl)chrysene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 50℃; for 1h; Suzuki Coupling; Inert atmosphere; Reflux;	35%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 0.666667h; Inert atmosphere; Reflux;	15%

6-bromochrysene (7397-93-5) → chrysene-6-boronic acid (858942-53-7)

Conditions	Yield
With n-butyllithium; Triisopropyl borate In hexane at -78 - 20℃; for 1.5h;	77%

6-bromochrysene (7397-93-5) + cyclohexane-1,2-epoxide (286-20-4) → 2-(6-chrysenyl)cyclohexanol (111209-23-5)

Conditions	Yield
With n-butyllithium 1.) hexane, ether, 2 h, 2.) ether, overnight; Yield given. Multistep reaction;
Stage #1: 6-bromochrysene With n-butyllithium In diethyl ether Stage #2: cyclohexane-1,2-epoxide In diethyl ether

6-bromochrysene (7397-93-5) + O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (236427-57-9) → 2-(6-chrysenyl)-O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80℃; for 16h; Buchwald-Hartwig amination;	40%

6-bromochrysene (7397-93-5) + anthracene-9-boronic acid (100622-34-2) → C32H20

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 5h; Reflux; Inert atmosphere;

9-phenyl-3,3'-bicarbazole (1060735-14-9) + 6-bromochrysene (7397-93-5) → C48H30N2

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-tert-butyl phosphine; potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;

6-bromochrysene (7397-93-5) + diphenylphosphane (829-85-6) → 6-diphenylphosphorylchrysene

Conditions	Yield
Stage #1: 6-bromochrysene; diphenylphosphane With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 60℃; for 24h; Stage #2: With dihydrogen peroxide In water for 3h;	40%

6-bromochrysene (7397-93-5) → C18H12Br(1+)

Conditions	Yield
With fluorosulfonylchloride; antimony pentafluoride; fluorosulphonic acid at -78℃; NMR-tube;

6-bromochrysene (7397-93-5) → 6-(2-formylphenyl)chrysene

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / triisopropylborate; n-BuLi / hexane / 1.5 h / -78 - 20 °C 2: 82 percent / cesium fluoride; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 14 h / Heating View Scheme

6-bromochrysene (7397-93-5) → cis-6-[2-(β-methoxyethenyl)phenyl]chrysene

Conditions	Yield
Multi-step reaction with 3 steps 1: 77 percent / triisopropylborate; n-BuLi / hexane / 1.5 h / -78 - 20 °C 2: 82 percent / cesium fluoride; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 14 h / Heating 3: PhLi / CH2Cl2; hexane / -78 - 20 °C View Scheme

6-bromochrysene (7397-93-5) → trans-6-[2-(β-methoxyethenyl)phenyl]chrysene

Conditions	Yield
Multi-step reaction with 3 steps 1: 77 percent / triisopropylborate; n-BuLi / hexane / 1.5 h / -78 - 20 °C 2: 82 percent / cesium fluoride; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 14 h / Heating 3: PhLi / CH2Cl2; hexane / -78 - 20 °C View Scheme

6-bromochrysene (7397-93-5) → 6-(2-formyl-4-methoxyphenyl)chrysene (858942-63-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / triisopropylborate; n-BuLi / hexane / 1.5 h / -78 - 20 °C 2: 87 percent / cesium fluoride; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 14 h / Heating View Scheme

6-bromochrysene (7397-93-5) → cis-6-[2-(β-methoxyethenyl)-4-methoxyphenyl]chrysene

Conditions	Yield
Multi-step reaction with 3 steps 1: 77 percent / triisopropylborate; n-BuLi / hexane / 1.5 h / -78 - 20 °C 2: 87 percent / cesium fluoride; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 14 h / Heating 3: PhLi / CH2Cl2; hexane / -78 - 20 °C View Scheme

6-bromochrysene (7397-93-5) → trans-6-[2-(β-methoxyethenyl)-4-methoxyphenyl]chrysene

Conditions	Yield
Multi-step reaction with 3 steps 1: 77 percent / triisopropylborate; n-BuLi / hexane / 1.5 h / -78 - 20 °C 2: 87 percent / cesium fluoride; Pd(PPh3)4 / 1,2-dimethoxy-ethane / 14 h / Heating 3: PhLi / CH2Cl2; hexane / -78 - 20 °C View Scheme

6-bromochrysene (7397-93-5) → C24H18 (111189-38-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) n-butyllithium / 1.) hexane, ether, 2 h, 2.) ether, overnight 2: 62 percent / pyridinium dichromate / dimethylformamide / Ambient temperature 3: 1.) polyphosphoric acid (PPA), 2.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / 1.) 110 deg C, 2 h, 2.) benzene, reflux, 30 min View Scheme

6-bromochrysene (7397-93-5) → C24H20 (111189-37-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) n-butyllithium / 1.) hexane, ether, 2 h, 2.) ether, overnight 2: 62 percent / pyridinium dichromate / dimethylformamide / Ambient temperature 3: 1.) polyphosphoric acid (PPA), 2.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / 1.) 110 deg C, 2 h, 2.) benzene, reflux, 30 min View Scheme

6-bromochrysene (7397-93-5) → 2-(6-chrysenyl)cyclohexanone (111189-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-butyllithium / 1.) hexane, ether, 2 h, 2.) ether, overnight 2: 62 percent / pyridinium dichromate / dimethylformamide / Ambient temperature View Scheme

6-bromochrysene (7397-93-5) → Naphtho<1,2b>fluoranthene (111189-32-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) n-butyllithium / 1.) hexane, ether, 2 h, 2.) ether, overnight 2: 62 percent / pyridinium dichromate / dimethylformamide / Ambient temperature 3: 1.) polyphosphoric acid (PPA), 2.) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / 1.) 110 deg C, 2 h, 2.) benzene, reflux, 30 min View Scheme

6-bromochrysene (7397-93-5) + trimethylsilylacetylene (1066-54-2) → Chrysen-6-ylethynyl-trimethyl-silane

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 1152h; Heating;	69%

6-bromochrysene (7397-93-5) → spiro[fluorene-9,15′-indeno[2,1-g]chrysene]

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol / 0.67 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: 1 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 1 h / 50 °C / Inert atmosphere; Reflux 2.1: n-butyllithium; sodium hydrogencarbonate / tetrahydrofuran; cyclohexane / 3 h / -78 - 20 °C / Inert atmosphere 2.2: 1 h / Reflux View Scheme

6-bromochrysene (7397-93-5) → 2,7-dibromospiro[fluorene-9,15′-indeno[2,1-g]chrysene]

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol / 0.67 h / Inert atmosphere; Reflux 2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: 1 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 1 h / 50 °C / Inert atmosphere; Reflux 2.1: n-butyllithium; sodium hydrogencarbonate / tetrahydrofuran; cyclohexane / 3 h / -78 - 20 °C / Inert atmosphere 2.2: 1 h / Reflux View Scheme

6-bromochrysene (7397-93-5) → 6-bromo-12-nitro-chrysene

Conditions	Yield
With nitric acid; nitrobenzene at 60℃;

6-bromochrysene (7397-93-5) → chrysene-6-carbonitrile (68723-50-2)

Conditions	Yield
With copper(l) cyanide at 320 - 360℃;

6-bromochrysene (7397-93-5) → 6-ethynylchrysene (36272-12-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / bis(triphenylphosphine)palladium dichloride, copper(I) iodide, triethylamine / 1152 h / Heating 2: 65 percent / potassium carbonate / methanol / 5 h / Ambient temperature View Scheme

6-bromochrysene (7397-93-5) → C55H33N

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 100 - 110 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / Inert atmosphere; Reflux View Scheme

6-bromochrysene (7397-93-5) → C55H33N

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 100 - 110 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / Inert atmosphere; Reflux View Scheme

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 218-01-9 chrysene 
• 71-43-2 benzene 
• 64-19-7 acetic acid 
• 7726-95-6 bromine 
• 89523-48-8 trans-5-acetoxy-6-bromo-5,6-dihydrochrysene 

Downstream Products

• 111209-23-5 2-(6-chrysenyl)cyclohexanol 
• 111189-38-9 C₂₄H₁₈ 
• 111189-37-8 C₂₄H₂₀ 
• 111189-36-7 2-(6-chrysenyl)cyclohexanone 
• 111189-32-3 naphtho[1,2-b]fluoranthene 
• 218-01-9 chrysene 
• 858942-63-9 6-(2-formyl-4-methoxyphenyl)chrysene 

Relevant academic research and scientific papers

The Role of π-f Orbital Interactions in Eu(III) Complexes for an Effective Molecular Luminescent Thermometer

Luminescent Eu(III) complexes with a ligand-to-metal charge transfer (LMCT) state were demonstrated for the development of a molecular thermometer. The Eu(III) complex was composed of three anionic ligands (hfa: hexafluoroacetylacetonate) and a phosphine oxide derivative containing a chrysene framework (diphenylphosphorylchrysene (DPCO)). The chrysene framework induced a rigid coordination structure via intermolecular interactions, resulting in a high thermal stability (decomposition point: 280 °C). The Eu(III) complex also exhibited an extremely high molar absorption coefficient (490000 cm-1 M-1), high intrinsic emission quantum yields (73%), and temperature-dependent energy migration between ligands and Eu(III) ion. The characteristic energy migration system was explained by the presence of the LMCT state based on π-f orbital interactions.

RARE-EARTH COMPLEX, LIGHT-EMITTING MATERIAL, LIGHT-EMITTING OBJECT, LIGHT-EMITTING DEVICE, INTERLAYER FOR LAMINATED GLASS, LAMINATED GLASS, WINDSHIELD FOR VEHICLE, WAVELENGTH CONVERSION MATERIAL, AND SECURITY MATERIAL

Disclosed is a rare-earth complex including a rare-earth ion, and a ligand coordinate-bonded to the rare-earth ion and having a condensed polycyclic aromatic group. The condensed polycyclic aromatic group is a residue formed by removing a hydrogen atom bonded to a condensed aromatic ring from a condensed polycyclic aromatic compound represented by the following Formula (I). In Formula (I), R1 and R2 represent hydrogen atoms or groups which are bonded to each other to form one aromatic ring or a condensed aromatic ring including two or more aromatic rings.

Palladium-Catalyzed Cascade Dearomative Spirocyclization and C?H Annulation of Aromatic Halides with Alkynes

Described herein is a palladium-catalyzed intermolecular dearomative annulation of aryl halides with alkynes, which provides a rapid approach to a class of structurally unique spiroembedded polycyclic aromatic compounds. The cascade process is accomplished by a sequential alkyne migratory insertion, Heck-type dearomatization, and C-H bond annulation. Further optoelectronic study indicated this fused spirocyclic scaffold could be a potential host material for OLEDs, as exemplified by a fabricated red PhOLED device with a maximum external quantum efficiency of 23.0%.

INDENOCHRYSENE DERIVATIVE AND ORGANIC LIGHT-EMITTING DEVICE USING SAME

There is provided an organic light-emitting device having an optical output with a high efficiency, a high luminance, and a long life. The organic light-emitting device includes an anode, a cathode, and a layer including an organic compound interposed between the anode and the cathode, in which either one of the anode and the cathode is formed of a transparent or translucent electrode material, and in which the layer includes at least one indenochrysene derivative represented by the general formula (1):

Policyclic Fluoranthene Hydrocarbons. 2. A New General Synthesis

A novel and efficient synthetic approach to policyclic fluoranthene hydrocarbons is described.The method entails fusion of an indeno ring to an appropriate alternant hydrocarbon via reaction of its aryllithium derivative with cyclohexene oxide, followed by oxidation, cyclodehydration, and aromatization.Cyclization of the cyclohexanone and cyclohexanol derivatives of the policyclic aromatic ring systems studied proceeds with high regioselectivity, and the direction of ring closure is predictable by molecular orbital methods.This synthetic approach provides a convenient general route to polyaromatic fluoranthene compounds, including potentially carcinogenic members of this class.Hydrocarbons synthesized by this method include benzacephenanthrylene (1), indenopyrene (2), indenochrysene (3), benzindenochrysene (4), fluorenochrysene (5), dibenzaceanthrylene (6), dibenzaceanthrylene (7), benzaceanthrylene (8), benzindenochrysene (9), fluorenochrysene (10), and dibenzacephenanthrylene (11).

FACILE SYNTHESIS OF K-REGION ARENE OXIDES

Polycyclic aromatic hydrocarbons reacts at the K-region with N-bromoacetamide in acetic acid to provide trans-bromohydrin acetates which are readly cyclized to arene oxides.The simplicity of the approach makes radioactive and optically active K-region arene oxides easily available.

Electrophilic aromatic reactivity. Part 27. Protiodetritiation of chrysene

All six monotritium-labelled chrysenes have been prepared, and their rates of protiodetritiation measured at 70°, using a mixture of trifluoroacetic acid-chloroform (9 : 1 v/v) as the exchanging medium. These lead to the following partial rate factors (positions in parentheses): 975 (1); 186 (2); 307 (3); 696 (4): 2790 (5); 12 200 (6) and the corresponding σ+ values are -0.342; -0.259; -0.284; -0.325; -0.394; -0.467. Hueckel localization energies predict a positional reactivity order, viz. 6 > 1 > 4 > 5 > 3 > 2 and reactivities relative to phenanthrene) close to that observed, only the 5-position being anomalous. Thus as in the case of helicenes, these calculations tend to underestimate the reactivity of the most central position in the molecule, though for chrysene, no localization of electrons at that point through ring distortion can be held responsible. Annelation rules, derived from hydrogen exchange data for other polycyclics, predict that the partial rate factor for the 5-position should be close to that observed. Reactivities in the terminal ring are only half that of the structural isomer benzo[c]phenanthrene (tetrahelicene) which further supports the view that distortion in the latter raises the reactivity through destabilization of the ground state. The relative reactivities of the unhindered positions in naphthalene, phenanthrene, and chrysene in acetylation are the inverse of that predicted by hydrogen exchange, and a possible reason for this is considered.