1732-26-9

Basic information

• Product Name: 4-bromopyrene
• Synonyms: 4-bromopyrene;Pyrene, 4-bromo-;AR-H 1 4-BROMOPYRENE
• CAS NO: 1732-26-9
• Molecular Formula: C16H9Br
• Molecular Weight: 281.1467
• Product Categories: Pyrenes
• Mol File: 1732-26-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 152 °C
• Boiling Point: 422.5 °C at 760 mmHg
• Flash Point: 209.4 °C
• Appearance: /
• Density: 1.578 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: 4-bromopyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromopyrene(1732-26-9)
• EPA Substance Registry System: 4-bromopyrene(1732-26-9)

Safety Data

• Hazardous Substances Data: 1732-26-9(Hazardous Substances Data)

Usage

Uses

4-Bromopyrene is an intermediate in the synthesis of Acepyrene (A130950), a novel constituent discovered that belongs to the pyrene class of the polycyclic aromatic hydrocarbons.

InChI:InChI=1/C16H9Br/c17-14-9-12-5-1-3-10-7-8-11-4-2-6-13(14)16(11)15(10)12/h1-9H

Synthetic route

4-Bromo-1,2,3,6,7,8-hexahydropyrene (1732-25-8) → 4-bromopyrene (1732-26-9)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 0.333333h; Heating / reflux;	58%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 0.333333h; Inert atmosphere; Reflux;	51%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 110℃; for 12h;	35%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone
dehydrogenation;

pyrene (129-00-0) → 4-bromopyrene (1732-26-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium / pentan-1-ol 2: bromine / acetic acid 3: dehydrogenation View Scheme
Multi-step reaction with 3 steps 1: sodium; pentan-1-ol / 2 h / Reflux 2: bromine / dichloromethane / 0.5 h / 20 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 12 h / 110 °C View Scheme

1,2,3,6,7,8-hexahydropyrene (1732-13-4) → 4-bromopyrene (1732-26-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / acetic acid 2: dehydrogenation View Scheme
Multi-step reaction with 2 steps 1: Br2 2: DDQ View Scheme
Stage #1: 1,2,3,6,7,8-hexahydropyrene With bromine; acetic acid In N,N-dimethyl-formamide at 20 - 80℃; for 1.5h; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 4h; Reflux;	2.9 g
Multi-step reaction with 2 steps 1: acetic acid; bromine / 1.5 h / 23 - 100 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: bromine / dichloromethane / 0.5 h / 20 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 12 h / 110 °C View Scheme

diphenylphosphinous acid methyl ester (4020-99-9) + 4-bromopyrene (1732-26-9) → diphenyl(pyren-1-yl)phosphane

Conditions	Yield
Stage #1: 4-bromopyrene With n-butyllithium In tetrahydrofuran at -70℃; for 0.333333h; Stage #2: diphenylphosphinous acid methyl ester In tetrahydrofuran at -70 - 20℃;	95%

4-bromopyrene (1732-26-9) → pyrene-1-d

Conditions	Yield
With 4-methyl-morpholine; tetrahydroxydiborane(4); 5%-palladium/activated carbon; DMAP-d6 In 1,2-dichloro-ethane at 50℃; for 9h;	93%

4-bromopyrene (1732-26-9) + (4-butylphenyl)acetylene (79887-09-5) → C28H22

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 90℃; for 12h; Inert atmosphere;	90%

4-bromopyrene (1732-26-9) + antimony(III) chloride (10025-91-9) → C48H27Sb*H2O

Conditions	Yield
Stage #1: 4-bromopyrene With n-butyllithium In diethyl ether; hexane at 0℃; for 1h; Stage #2: antimony(III) chloride In diethyl ether; hexane at 20℃;	90%

4-bromopyrene (1732-26-9) → C48H27P

Conditions	Yield
Stage #1: 4-bromopyrene With n-butyllithium In diethyl ether; hexane at 0℃; for 1h; Stage #2: With phosphorus trichloride In diethyl ether; hexane at 20℃;	86%

4-bromopyrene (1732-26-9) → pyrene (129-00-0)

Conditions	Yield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 3h;	86%

4-bromopyrene (1732-26-9) + N‐{[1,1'‐biphenyl]‐2‐yl}‐9,9‐dimethylfluoren‐2‐amine → C43H31N

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere;	85.6%

4-bromopyrene (1732-26-9) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(pyren-4-yl)-1,3,2-dioxaborolane

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 4h; Inert atmosphere;	85%
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;	66%
With potassium carbonate; palladium In N,N-dimethyl-formamide at 90 - 120℃; Inert atmosphere;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 80℃; for 10h; Inert atmosphere;

4-bromopyrene (1732-26-9) + (3a1,6-dihydropyren-1-yl)boronic acid (496839-55-5) → 1,4'-bipyrenyl

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 80℃; for 24h; Suzuki Coupling; Inert atmosphere;	82%

4-bromopyrene (1732-26-9) + 9,9-dimethyl-9H-fluorene-2-carboxamide → 9,9-dimethyl-N-(pyren-4-yl)-9H-fluorene-2-carboxamide

Conditions	Yield
Stage #1: 4-bromopyrene; 9,9-dimethyl-9H-fluorene-2-carboxamide With caesium carbonate; N,N-dimethylethylenediamine In 1,4-dioxane for 0.5h; Inert atmosphere; Stage #2: With copper(l) iodide In 1,4-dioxane at 120℃; for 0.25h; Inert atmosphere;	81.4%

4-bromopyrene (1732-26-9) → 4,4’-bipyrenyl (96631-99-1)

Conditions	Yield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0); cyclo-octa-1,5-diene In N,N-dimethyl-formamide; toluene at 80℃; for 24h; Schlenk technique; Glovebox;	81%
(electrochemical reduction);

4-bromopyrene (1732-26-9) → C48H27As

Conditions	Yield
Stage #1: 4-bromopyrene With n-butyllithium In diethyl ether; hexane at 0℃; for 1h; Stage #2: With arsenic trichloride In diethyl ether; hexane at 20℃;	80%

4-bromopyrene (1732-26-9) → 4-iodopyrene (78751-65-2)

Conditions	Yield
With copper(l) iodide; potassium iodide In 1,3-dimethyl-2-imidazolidinone at 160℃; Inert atmosphere;	79%
Stage #1: 4-bromopyrene With n-butyllithium Stage #2: With iodine

4-bromopyrene (1732-26-9) + bismuth(III) chloride (7787-60-2) → C48H27Bi

Conditions	Yield
Stage #1: 4-bromopyrene With n-butyllithium In diethyl ether; hexane at 0℃; for 1h; Stage #2: bismuth(III) chloride In diethyl ether; hexane at 20℃;	79%

4-bromopyrene (1732-26-9) + 3,4-methylenedioxyphenylacetonitrile (4439-02-5) → 5-(3,4-methylendioxyphenylmethyl)-4-pyrenecarbonitrile

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -40 deg C, 2.) r.t., 8 h;	77%

4-bromopyrene (1732-26-9) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → N-Boc-(R)-2-(4-pyrenyl)pyrrolidine (1222923-23-0)

Conditions

Yield

Stage #1: tert-butyl pyrrolidine-1-carboxylate With sec.-butyllithium; (-)-sparteine In tert-butyl methyl ether; cyclohexane at -78℃; for 3h; Stage #2: With zinc(II) chloride In diethyl ether; tert-butyl methyl ether; cyclohexane at -78 - 20℃; Stage #3: 4-bromopyrene With tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate In diethyl ether; tert-butyl methyl ether; cyclohexane at 20℃; for 16h;

77%

4-bromopyrene (1732-26-9) + para-thiocresol (106-45-6) → pyren-4-yl(p-tolyl)sulfide

Conditions	Yield
Stage #1: 4-bromopyrene; para-thiocresol In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With sodium hydride In N,N-dimethyl-formamide for 10.1667h; Inert atmosphere; Reflux;	77%
With potassium hydroxide In dimethyl sulfoxide at 130℃; for 24h; Sealed tube; Inert atmosphere;

2,6-dibromobenzo[1,2-b:4,5-b']dithiophene-4,8-phenylhydrazine (196491-93-7) + 4-bromopyrene (1732-26-9) → 2,6-dibromo-4,8-bis(4-pyrenyl)benzo[1,2-b:4,5-b']dithiophene

Conditions	Yield
Stage #1: 4-bromopyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2,6-dibromobenzo[1,2-b:4,5-b']dithiophene-4,8-phenylhydrazine In tetrahydrofuran; hexane at -78 - 20℃; for 9.5h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water for 4h; Reflux; Inert atmosphere;	77%

3,4-dimethoxyphenylacetonitrile (93-17-4) + 4-bromopyrene (1732-26-9) → 5-(3,4-dimethoxyphenylmethyl)-4-pyrenecarbonitrile

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -40 deg C, 2.) r.t., 8 h;	74%

4-bromopyrene (1732-26-9) + 2'-deoxy-D-adenosine (958-09-8) → N6-(pyren-1-yl)-2'-deoxyadenosine

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 110℃; for 6h;	70%

4-bromopyrene (1732-26-9) + N-butylamine (109-73-9) → N-butylpyren-4-amine

Conditions	Yield
With palladium diacetate; tri-tert-butylamine; sodium t-butanolate In 1,4-dioxane at 80℃; for 19h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	70%

(thiophen-3-yl)acetonitrile (13781-53-8) + 4-bromopyrene (1732-26-9) → 5-(3-thienylmethyl)-4-pyrenecarbonitrile

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -40 deg C, 2.) r.t., 8 h;	68%

thieno[3,2-b]thiophene (251-41-2) + 4-bromopyrene (1732-26-9) → C22H12S2

Conditions	Yield
With PdCl(C3H5)(1,4-bis(diphenylphosphino)butane); potassium acetate In N,N-dimethyl acetamide at 120℃; for 14h; Inert atmosphere;	67%

4-bromopyrene (1732-26-9) + Spiro-10'-on (92638-83-0) → C42H25NO

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Inert atmosphere; Reflux;	67%

4-bromopyrene (1732-26-9) + ethyl acrylate (140-88-5) → (E)-ethyl 3-(pyren-4-yl)acrylate

Conditions	Yield
With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide for 6h; Heck Reaction; Reflux; Inert atmosphere;	65%

4-bromopyrene (1732-26-9) + p-methoxybenzylnitrile (104-47-2) → 5-(4-methoxyphenylmethyl)-4-pyrenecarbonitrile

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -40 deg C, 2.) r.t., 8 h;	63%

carbon dioxide (124-38-9) + 4-bromopyrene (1732-26-9) → pyrene-4-carboxylic acid (22245-48-3)

Conditions	Yield
Stage #1: 4-bromopyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 - 20℃; for 19h;	63%

4-bromopyrene (1732-26-9) + trimethylsilylacetylene (1066-54-2) → trimethyl(pyren-4-ylethynyl)silane (600168-40-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 60℃; Sonogashira coupling;	62%
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran Sonogashira Cross-Coupling;

pyridine-2-acetonitrile (2739-97-1) + 4-bromopyrene (1732-26-9) → 5-(2-pyridylmethyl)-4-pyrenecarbonitrile

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -40 deg C, 2.) r.t., 8 h;	58%

Upstream product

• 1732-13-4 1,2,3,6,7,8-hexahydropyrene 
• 129-00-0 pyrene 
• 1732-25-8 4-bromohexahydro-1,2,3,6,7,8-pyrene 

Downstream Products

• 111209-32-6 2-(4-pyrenyl)cyclohexanol 
• 111189-40-3 2-(4-pyrenyl)cyclohexanone 
• 22245-51-8 pyrene-1-carbaldehyde 
• 3353-12-6 4-methylpyrene 
• 110954-36-4 diphenyl(pyren-1-yl)phosphane 
• 193-39-5 Indeno[1,2,3-cd]pyrene 
• 73529-24-5 4-oxiranylpyrene 
• 22245-55-2 pyren-4-ylacetic acid 
• 27208-37-3 cyclopenta[c,d]pyrene 
• 69795-70-6 cyclopentapyrene-3(4H)-one 
• 69795-73-9 3-hydroxy-3,4-dihydrocyclopentapyrene 
• 1222923-23-0 N-Boc-(R)-2-(4-pyrenyl)pyrrolidine 
• 1377273-10-3 (1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(pyren-4-ylethynyl)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide 
• 1388186-92-2 C₄₁H₃₃ClN₆O₃ 

Relevant articles and documents

Phenanthroquinazoline-core compounds

Provided is a composition comprising one or more phenanthroquinazoline-core compounds having structure (I)wherein each of R 1 and R 2 is independently a substituted or unsubstituted phenyl group.

Derivatised molecules for mass spectrometry

Compounds of formula (IIa): are provided where:X is a group capable of being cleaved from the α-carbon atom to form an ion of formula (I')C is a carbon atom bearing a single positive charge or a single negative charge; The invention further provides compounds of formula (IIb): where:X is a counter-ion to C. The compounds of formula (IIa) and (IIb) may form ions of formula (I') by either cleaving the C-X bond between X and the α-carbon atoms in the case of the compounds of formula (IIa) or dissociating X in the case of compounds of formula (IIb).