Product Name

  • Name

    4-bromopyrene

  • EINECS
  • CAS No. 1732-26-9
  • Article Data9
  • CAS DataBase
  • Density 1.578 g/cm3
  • Solubility
  • Melting Point 152 °C
  • Formula C16H9Br
  • Boiling Point 422.5 °C at 760 mmHg
  • Molecular Weight 281.151
  • Flash Point 209.4 °C
  • Transport Information
  • Appearance
  • Safety 2
  • Risk Codes
  • Molecular Structure Molecular Structure of 1732-26-9 (4-bromopyrene)
  • Hazard Symbols
  • Synonyms 4-Bromopyrene;
  • PSA 0.00000
  • LogP 5.34650

Synthetic route

4-Bromo-1,2,3,6,7,8-hexahydropyrene
1732-25-8

4-Bromo-1,2,3,6,7,8-hexahydropyrene

4-bromopyrene
1732-26-9

4-bromopyrene

Conditions
ConditionsYield
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

pyrene

4-bromopyrene
1732-26-9

4-bromopyrene

Conditions
ConditionsYield
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

1,2,3,6,7,8-hexahydropyrene

4-bromopyrene
1732-26-9

4-bromopyrene

Conditions
ConditionsYield
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

diphenylphosphinous acid methyl ester

4-bromopyrene
1732-26-9

4-bromopyrene

diphenyl(pyren-1-yl)phosphane

diphenyl(pyren-1-yl)phosphane

Conditions
ConditionsYield
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

4-bromopyrene

pyrene-1-d

pyrene-1-d

Conditions
ConditionsYield
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-bromopyrene

(4-butylphenyl)acetylene
79887-09-5

(4-butylphenyl)acetylene

C28H22

C28H22

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 90℃; for 12h; Inert atmosphere;90%
4-bromopyrene
1732-26-9

4-bromopyrene

antimony(III) chloride
10025-91-9

antimony(III) chloride

C48H27Sb*H2O

C48H27Sb*H2O

Conditions
ConditionsYield
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

4-bromopyrene

C48H27P

C48H27P

Conditions
ConditionsYield
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

4-bromopyrene

pyrene
129-00-0

pyrene

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 3h;86%
4-bromopyrene
1732-26-9

4-bromopyrene

N‐{[1,1'‐biphenyl]‐2‐yl}‐9,9‐dimethylfluoren‐2‐amine

N‐{[1,1'‐biphenyl]‐2‐yl}‐9,9‐dimethylfluoren‐2‐amine

C43H31N

C43H31N

Conditions
ConditionsYield
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

4-bromopyrene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-2-(pyren-4-yl)-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-(pyren-4-yl)-1,3,2-dioxaborolane

Conditions
ConditionsYield
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

4-bromopyrene

(3a1,6-dihydropyren-1-yl)boronic acid
496839-55-5

(3a1,6-dihydropyren-1-yl)boronic acid

1,4'-bipyrenyl

1,4'-bipyrenyl

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 80℃; for 24h; Suzuki Coupling; Inert atmosphere;82%
4-bromopyrene
1732-26-9

4-bromopyrene

9,9-dimethyl-9H-fluorene-2-carboxamide

9,9-dimethyl-9H-fluorene-2-carboxamide

9,9-dimethyl-N-(pyren-4-yl)-9H-fluorene-2-carboxamide

9,9-dimethyl-N-(pyren-4-yl)-9H-fluorene-2-carboxamide

Conditions
ConditionsYield
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-bromopyrene

4,4’-bipyrenyl
96631-99-1

4,4’-bipyrenyl

Conditions
ConditionsYield
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

4-bromopyrene

C48H27As

C48H27As

Conditions
ConditionsYield
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-bromopyrene

4-iodopyrene
78751-65-2

4-iodopyrene

Conditions
ConditionsYield
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

4-bromopyrene

bismuth(III) chloride
7787-60-2

bismuth(III) chloride

C48H27Bi

C48H27Bi

Conditions
ConditionsYield
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

4-bromopyrene

3,4-methylenedioxyphenylacetonitrile
4439-02-5

3,4-methylenedioxyphenylacetonitrile

5-(3,4-methylendioxyphenylmethyl)-4-pyrenecarbonitrile

5-(3,4-methylendioxyphenylmethyl)-4-pyrenecarbonitrile

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -40 deg C, 2.) r.t., 8 h;77%
4-bromopyrene
1732-26-9

4-bromopyrene

tert-butyl pyrrolidine-1-carboxylate
86953-79-9

tert-butyl pyrrolidine-1-carboxylate

N-Boc-(R)-2-(4-pyrenyl)pyrrolidine
1222923-23-0

N-Boc-(R)-2-(4-pyrenyl)pyrrolidine

Conditions
ConditionsYield
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

4-bromopyrene

para-thiocresol
106-45-6

para-thiocresol

pyren-4-yl(p-tolyl)sulfide

pyren-4-yl(p-tolyl)sulfide

Conditions
ConditionsYield
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

2,6-dibromobenzo[1,2-b:4,5-b']dithiophene-4,8-phenylhydrazine

4-bromopyrene
1732-26-9

4-bromopyrene

2,6-dibromo-4,8-bis(4-pyrenyl)benzo[1,2-b:4,5-b']dithiophene

2,6-dibromo-4,8-bis(4-pyrenyl)benzo[1,2-b:4,5-b']dithiophene

Conditions
ConditionsYield
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

3,4-dimethoxyphenylacetonitrile

4-bromopyrene
1732-26-9

4-bromopyrene

5-(3,4-dimethoxyphenylmethyl)-4-pyrenecarbonitrile

5-(3,4-dimethoxyphenylmethyl)-4-pyrenecarbonitrile

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -40 deg C, 2.) r.t., 8 h;74%
4-bromopyrene
1732-26-9

4-bromopyrene

2'-deoxy-D-adenosine
958-09-8

2'-deoxy-D-adenosine

N6-(pyren-1-yl)-2'-deoxyadenosine

N6-(pyren-1-yl)-2'-deoxyadenosine

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 110℃; for 6h;70%
4-bromopyrene
1732-26-9

4-bromopyrene

N-butylamine
109-73-9

N-butylamine

N-butylpyren-4-amine

N-butylpyren-4-amine

Conditions
ConditionsYield
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

(thiophen-3-yl)acetonitrile

4-bromopyrene
1732-26-9

4-bromopyrene

5-(3-thienylmethyl)-4-pyrenecarbonitrile

5-(3-thienylmethyl)-4-pyrenecarbonitrile

Conditions
ConditionsYield
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

thieno[3,2-b]thiophene

4-bromopyrene
1732-26-9

4-bromopyrene

C22H12S2

C22H12S2

Conditions
ConditionsYield
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

4-bromopyrene

Spiro-10'-on
92638-83-0

Spiro-10'-on

C42H25NO

C42H25NO

Conditions
ConditionsYield
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

4-bromopyrene

ethyl acrylate
140-88-5

ethyl acrylate

(E)-ethyl 3-(pyren-4-yl)acrylate

(E)-ethyl 3-(pyren-4-yl)acrylate

Conditions
ConditionsYield
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

4-bromopyrene

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

5-(4-methoxyphenylmethyl)-4-pyrenecarbonitrile

5-(4-methoxyphenylmethyl)-4-pyrenecarbonitrile

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -40 deg C, 2.) r.t., 8 h;63%
carbon dioxide
124-38-9

carbon dioxide

4-bromopyrene
1732-26-9

4-bromopyrene

pyrene-4-carboxylic acid
22245-48-3

pyrene-4-carboxylic acid

Conditions
ConditionsYield
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

4-bromopyrene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

trimethyl(pyren-4-ylethynyl)silane
600168-40-9

trimethyl(pyren-4-ylethynyl)silane

Conditions
ConditionsYield
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

pyridine-2-acetonitrile

4-bromopyrene
1732-26-9

4-bromopyrene

5-(2-pyridylmethyl)-4-pyrenecarbonitrile

5-(2-pyridylmethyl)-4-pyrenecarbonitrile

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

Pyrene, 4-bromo- Specification

The Pyrene, 4-bromo- has CAS registry number 1732-26-9. It belongs to the product category of Pyrenes. This chemical's molecular formula is C16H9Br and molecular weight is 281.1467. What's more, its IUPAC name is 4-Bromopyrene. In addition, it should be kept out of the reach of children.

Physical properties about Pyrene, 4-bromo- are: (1)ACD/LogP: 5.94; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.94; (4)ACD/LogD (pH 7.4): 5.94; (5)ACD/BCF (pH 5.5): 19338.63; (6)ACD/BCF (pH 7.4): 19338.63; (7)ACD/KOC (pH 5.5): 40720.2; (8)ACD/KOC (pH 7.4): 40720.2; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.858; (14)Molar Refractivity: 80.15 cm3; (15)Molar Volume: 178.1 cm3; (16)Polarizability: 31.77×10-24 cm3; (17)Surface Tension: 62.1 dyne/cm; (18)Density: 1.578 g/cm3; (19)Flash Point: 209.4 °C; (20)Enthalpy of Vaporization: 65.05 kJ/mol; (21)Boiling Point: 422.5 °C at 760 mmHg; (22)Vapour Pressure: 5.91E-07 mmHg at 25 °C.

Uses of Pyrene, 4-bromo-: it is used to produce other chemicals. For example, it is used to produce 9, 12-Dihydro-9, 12-epoxybenzo[e]pyrene by heating. The reaction needs reagent Sodium amide and solvent Tetrahydrofuran. The reaction time is 4 hours. The yield is about 21 %.

(2E)-3-Phenylprop-2-en-1-ol can react with Furan to get 9, 12-Dihydro-9, 12-epoxybenzo[e]pyrene.

You can still convert the following datas into molecular structure:
(1) SMILES: Brc4cc2cccc1ccc3c(c12)c4ccc3
(2) 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
(3) InChIKey: QMHTZTOPYZKQLC-UHFFFAOYAG

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