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27973-29-1

Basic Information
CAS No.: 27973-29-1
Name: 1,6-Dibromopyrene
Molecular Structure:
Molecular Structure of 27973-29-1 (1,6-Dibromopyrene)
Formula: C16H8Br2
Molecular Weight: 360.04
Synonyms: pyrene, 1,6-dibromo-;
EINECS: 1308068-626-2
Density: 1.852 g/cm3
Melting Point: 228.0 to 232.0 °C
Boiling Point: 469.6 °C at 760 mmHg
Flash Point: 277.3 °C
Solubility:
Appearance: White to off-white powder
Hazard Symbols:
Risk Codes: 36/37/38
Safety: 26-36/37/39
Transport Information:
PSA: 0.00000
LogP: 6.10900
Synthetic route
129-00-0

pyrene

A

27973-29-1

1,6-dibromopyrene

B

38303-35-4

1,8-dibromopyrene

Conditions
ConditionsYield
With carbon disulfide; bromine at 20℃; for 17h;A 15%
B 85%
With carbon disulfide; bromine at 20℃; for 17h;A 15%
B 85%
With bromine In chloroform for 4h; Inert atmosphere; Reflux;A 71.1%
B 20%

C18H16Br2O2

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;82.2%

C24H28Br2O2

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With methanesulfonic acid In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;78.33%
129-00-0

pyrene

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With bromine In dichloromethane at 20℃; for 30h;64%
With bromine In tetrachloromethane at 110℃; for 12h; Darkness;63%
With bromine In chloroform at 23℃; for 8h;63%

1-hydropyrenyl

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With bromine In chloroform at 20℃;30%
1714-29-0

1-bromopyrene

A

38037-54-6

1,3-dibromopyrene

B

27973-29-1

1,6-dibromopyrene

C

38303-35-4

1,8-dibromopyrene

Conditions
ConditionsYield
With bromine In dichloromethane for 5h; Ambient temperature;A 3 % Spectr.
B 53 % Spectr.
C 44 % Spectr.
42882-08-6

1-amino-6-bromopyrene

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
(i) NaNO2, aq. H2SO4, DMF, (ii) CuBr, KBr, aq. HBr; Multistep reaction;
129-00-0

pyrene

75-09-2

dichloromethane

7726-95-6

bromine

A

27973-29-1

1,6-dibromopyrene

B

38303-35-4

1,8-dibromopyrene

1714-29-0

1-bromopyrene

A

27973-29-1

1,6-dibromopyrene

B

38303-35-4

1,8-dibromopyrene

C

38303-36-5

1,3,6-tribromopyrene

Conditions
ConditionsYield
With sodium hypochlorite; potassium bromide In methanol for 24h; pH=5;A n/a
B n/a
C 20 mg
42882-03-1

1-bromo-6-nitropyrene

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N2H4*H2O / Raney-Ni
2: (i) NaNO2, aq. H2SO4, DMF, (ii) CuBr, KBr, aq. HBr
View Scheme

2Br(1-)*C16H8N4(2+)

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
With hydrogen bromide; copper(I) bromide In water at 60℃; for 0.5h;
129-00-0

pyrene

A

27973-29-1

1,6-dibromopyrene

B

857992-38-2

1,4-dibromopyrene

Conditions
ConditionsYield
With bromine In tetrachloromethane
129-00-0

pyrene

A

27973-29-1

1,6-dibromopyrene

B

38303-35-4

1,8-dibromopyrene

C

38303-36-5

1,3,6-tribromopyrene

Conditions
ConditionsYield
With bromine In tetrachloromethane at 20℃; for 12h;
129-00-0

pyrene

77-48-5

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

A

27973-29-1

1,6-dibromopyrene

B

38303-35-4

1,8-dibromopyrene

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h; Overall yield = 97 %; Overall yield = 398 mg;
10462-33-6

3,3'-dibromo-2,2'-diamino-1,1'-biphenyl

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogen iodide; sulfuric acid / 0.17 h / 5 °C / Reflux
1.2: 3 h / 25 - 60 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
2.2: 20 °C
3.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
3.2: 2 h / 5 - 30 °C
4.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme

3,3'-dibromo-2,2'-diiodo-1,1'-biphenyl

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
1.2: 20 °C
2.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
2.2: 2 h / 5 - 30 °C
3.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
16400-51-4

3,3'-dibromobiphenyl

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: nitric acid; sulfuric acid / dichloromethane / 4 h / 5 - 25 °C
2.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
3.1: hydrogen iodide; sulfuric acid / 0.17 h / 5 °C / Reflux
3.2: 3 h / 25 - 60 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
4.2: 20 °C
5.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
5.2: 2 h / 5 - 30 °C
6.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme

3,3'-dibromo-2,2'-dinitro-1,1'-biphenyl

27973-29-1

1,6-dibromopyrene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogen; 5%-palladium/activated carbon / ethanol / 40 °C / 2250.23 Torr / Autoclave
2.1: hydrogen iodide; sulfuric acid / 0.17 h / 5 °C / Reflux
2.2: 3 h / 25 - 60 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -85 °C / Inert atmosphere
3.2: 20 °C
4.1: sodium t-butanolate / tetrahydrofuran / 0.5 h / 5 °C
4.2: 2 h / 5 - 30 °C
5.1: methanesulfonic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
27973-29-1

1,6-dibromopyrene

180283-59-4

1,1-dimethylethyl 2-ethenyl-1H-pyrrole-1-carboxylate

1,6-bis((E)-2-(1H-pyrrol-2-yl)vinyl)pyrene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; acetylacetone In N,N-dimethyl-formamide at 130℃; for 6h; Heck Reaction; Inert atmosphere; Sealed tube;100%
27973-29-1

1,6-dibromopyrene

98-80-6

phenylboronic acid

55009-75-1

1,6-diphenylpyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 8h; Suzuki Coupling;99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Suzuki Coupling; Inert atmosphere; Reflux;90%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene Reflux;87%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 5h; Inert atmosphere; Reflux;60%
27973-29-1

1,6-dibromopyrene

32316-92-0

naphthalene-2-boronic acid

663954-28-7

1,6-bis(2-naphthyl)pyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 1,2-dimethoxyethane; water at 90℃; for 8h;99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 24h; Suzuki coupling; Reflux; Inert atmosphere;71%
27973-29-1

1,6-dibromopyrene

73183-34-3

bis(pinacol)diborane

950779-13-2

1,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyrene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 16h; Miyaura Borylation Reaction; Schlenk technique; Inert atmosphere;99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;87.6%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;87%
27973-29-1

1,6-dibromopyrene

copper(l) cyanide

27973-30-4

pyrene-1,6-dicarbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 150℃; for 24h;99%
In N,N-dimethyl-formamide at 170℃;93%
In N,N-dimethyl-formamide at 150℃; for 10h; Inert atmosphere;80%
27973-29-1

1,6-dibromopyrene

126726-62-3

2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

C22H18

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 70 - 75℃; for 5.5h; Inert atmosphere;98.54%
27973-29-1

1,6-dibromopyrene

126747-14-6

4-cyanophenylboronic acid

1,6-di(4-cyanophenyl)pyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 1,2-dimethoxyethane; water at 90℃; for 8h;98%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 72h; Inert atmosphere;61.18%
1208149-33-0

4-isopropylphenyl-3,5-dimethylphenylamine

27973-29-1

1,6-dibromopyrene

C50H48N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;98%
27973-29-1

1,6-dibromopyrene

63451-41-2

4-(1-methylethyl)-N-[4-(1-methylethyl)phenyl]benzenamine

C52H52N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;97%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 6h; Reflux; Inert atmosphere;62%
27973-29-1

1,6-dibromopyrene

4688-76-0

2-Biphenylboronic acid

1,6-di(2-biphenyl)pyrene

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 8h;97%
27973-29-1

1,6-dibromopyrene

63451-41-2

4-(1-methylethyl)-N-[4-(1-methylethyl)phenyl]benzenamine

C52H52N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;97%
27973-29-1

1,6-dibromopyrene

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

C24H22

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 70 - 75℃; for 5.5h; Inert atmosphere;96.4%
27973-29-1

1,6-dibromopyrene

1066-54-2

trimethylsilylacetylene

1,6-bis((trimethylsilyl)ethynyl)pyrene

Conditions
ConditionsYield
Stage #1: 1,6-dibromopyrene With copper(l) iodide; triethylamine; triphenylphosphine for 0.5h; Inert atmosphere;
Stage #2: trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride for 18h; Reflux; Inert atmosphere;
94%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 80℃;93%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran; toluene at 120℃; for 1h; Microwave irradiation;88%
288-13-1

NH-pyrazole

27973-29-1

1,6-dibromopyrene

C22H14N4

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 40h; Schlenk technique; Inert atmosphere;94%
494834-22-9

4-isopropyl-N-(para-tolyl)aniline

27973-29-1

1,6-dibromopyrene

C48H44N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;93%
494834-22-9

4-isopropyl-N-(para-tolyl)aniline

27973-29-1

1,6-dibromopyrene

C48H44N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate at 100℃;93%
27973-29-1

1,6-dibromopyrene

1292285-22-3

N-(3-methylphenyl)-3-(9-phenyl-9H-fluoren-9-yl)phenylamine

1292285-21-2

N,N'-bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-pyrene-1,6-diamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene at 60 - 80℃; for 3h; Inert atmosphere;93%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In hexane; toluene at 60 - 80℃; for 3h; Inert atmosphere;93%
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In hexane; toluene at 80℃; for 3h; Inert atmosphere;67%
5350-57-2

benzophenone hydrazone

27973-29-1

1,6-dibromopyrene

C42H30N4

Conditions
ConditionsYield
With palladium diacetate; sodium t-butanolate; XPhos In toluene at 90℃; for 3h;93%
27973-29-1

1,6-dibromopyrene

1245928-51-1

(4-(tert-butyl)-2-methoxyphenyl)boronic acid

C38H38O2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In 1,4-dioxane; water at 100℃; Inert atmosphere;93%
27973-29-1

1,6-dibromopyrene

(4-(2-(3-methylphenyl)benzimidazol-1-yl)phenyl)boronic acid

C56H38N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 10h; Inert atmosphere; Reflux;93%
27973-29-1

1,6-dibromopyrene

55389-75-8

bis-(3,4-dimethyl-phenyl)-amine

C48H44N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;92%
27973-29-1

1,6-dibromopyrene

55389-75-8

bis-(3,4-dimethyl-phenyl)-amine

C48H44N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;92%
27973-29-1

1,6-dibromopyrene

32228-99-2

4-phenyldiphenylamine

C52H36N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;92%
27973-29-1

1,6-dibromopyrene

5720-05-8

4-methylphenylboronic acid

908011-87-0

1,6-bis(4-methylphenyl)pyrene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Suzuki Coupling; Inert atmosphere; Reflux;92%
27973-29-1

1,6-dibromopyrene

2-fluoro-4-(2-phenylbenzimidazolyl)benzeneboronic acid

C54H32F2N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 15h; Suzuki Coupling; Inert atmosphere; Reflux;91%
27973-29-1

1,6-dibromopyrene

C19H14BFN2O2

C54H32F2N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 15h; Inert atmosphere; Reflux;91%
27973-29-1

1,6-dibromopyrene

123324-71-0

4-tert-butylphenylboronic acid

1,6-bis(4-tert-butylphenyl)pyrene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 85℃; for 16h; Inert atmosphere;91%
27973-29-1

1,6-dibromopyrene

17049-49-9

octylmagnesium bromide

1185354-41-9

1,6-dioctylpyrene

Conditions
ConditionsYield
Stage #1: octylmagnesium bromide With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); zinc(II) chloride In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: 1,6-dibromopyrene In tetrahydrofuran for 24h; Reflux;
91%
27973-29-1

1,6-dibromopyrene

532-18-3

2,2'-dinaphthylamine

C56H36N2

Conditions
ConditionsYield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 100℃;90%
27973-29-1

1,6-dibromopyrene

[4‐(5‐methyl‐2‐phenyl‐1H‐1,3‐benzodiazol‐1‐yl)phenyl]boronic acid

C56H38N4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 10h; Inert atmosphere; Reflux;90%
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    1,6-Dibromopyrene

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    27973-29-1

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    1,6-Dibromopyrene Basic information Product Name: 1,6-Dibromopyrene Synonyms: 1,6-Dibromopyrene;1,6-dlbrornopyrone;6-DibroMopyrene CAS: 27973-29-1

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    27973-29-1

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    Located in Hangzhou National Hi-Tech Industrial Development Zone, zhongqichem is a technical company mainly focus on the Custom synthesis, manufacturing, sales of chemicals to various industries. Benefiting from the outstanding customer service and h

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Chemistry

Molecular Structure of 1,6-Dibromopyrene (CAS NO.27973-29-1):

IUPAC Name: 1,6-dibromopyrene 
Empirical Formula: C16H8Br2
Molecular Weight: 360.0427
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 0 Å2
Index of Refraction: 1.863
Molar Refractivity: 87.84 cm3
Molar Volume: 194.3 cm3
Surface Tension: 64.4 dyne/cm
Density: 1.852 g/cm3
Flash Point: 277.3 °C
Enthalpy of Vaporization: 70.4 kJ/mol
Boiling Point: 469.6 °C at 760 mmHg
Vapour Pressure: 1.54E-08 mmHg at 25°C
InChI
InChI=1/C16H8Br2/c17-13-8-4-10-2-6-12-14(18)7-3-9-1-5-11(13)16(10)15(9)12/h1-8H
Smiles
c1(ccc2ccc3c(ccc4ccc1c2c34)Br)Br

Specification

 1,6-Dibromopyrene , with CAS number of 27973-29-1, can be called pyrene, 1,6-dibromo- .

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