7397-93-5

Basic information

• Product Name: 6-BroMochrysene
• Synonyms: 6-BroMochrysene
• CAS NO: 7397-93-5
• Molecular Formula: C₁₈H₁₁Br
• Molecular Weight: 307
• Mol File: 7397-93-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 152-154 °C(Solv: benzene (71-43-2))
• Boiling Point: 482.9°Cat760mmHg
• Flash Point: 244.7°C
• Appearance: /
• Density: 1.477g/cm³
• Vapor Pressure: 5.14E-09mmHg at 25°C
• Refractive Index: 1.782
• CAS DataBase Reference: 6-BroMochrysene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BroMochrysene(7397-93-5)
• EPA Substance Registry System: 6-BroMochrysene(7397-93-5)

Safety Data

• Hazardous Substances Data: 7397-93-5(Hazardous Substances Data)

Usage

General Description

6-Bromochrysene is a synthetic polycyclic aromatic hydrocarbon compound with the chemical formula C18H11Br. It is derived from chrysene, a natural constituent of coal tar, and contains a bromine atom attached to the sixth carbon in the chrysene molecule. 6-Bromochrysene is known to exhibit mutagenic activity in various in vitro and in vivo assays, and has been implicated in the induction of mammary gland tumors in female rats. Due to its potential carcinogenic and mutagenic properties, 6-bromochrysene is often used as a reference standard in toxicological studies to assess the health risks associated with exposure to polycyclic aromatic hydrocarbons. It is important to handle 6-bromochrysene with caution and follow safety protocols to minimize the risk of exposure.

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

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

Downstream Products

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

Relevant articles and documents

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