1,6-Dibromopyrene supplier | CasNO.27973-29-1

Name
1,6-Dibromopyrene
EINECS 1308068-626-2
CAS No. 27973-29-1
Article Data53
CAS DataBase
Density 1.852 g/cm³
Solubility
Melting Point 228.0 to 232.0 °C
Formula C₁₆H₈Br₂
Boiling Point 469.6 °C at 760 mmHg
Molecular Weight 360.048
Flash Point 277.3 °C
Transport Information
Appearance White to off-white powder
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms pyrene, 1,6-dibromo-;
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

Conditions	Yield
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

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

: C24H28Br2O2

: 27973-29-1
1,6-dibromopyrene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With bromine In dichloromethane for 5h; Ambient temperature;	A 3 % Spectr. B 53 % Spectr. C 44 % Spectr.

...Expand

: 42882-08-6
1-amino-6-bromopyrene

: 27973-29-1
1,6-dibromopyrene

Conditions

Conditions	Yield
(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

...Expand

: 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

Conditions	Yield
With sodium hypochlorite; potassium bromide In methanol for 24h; pH=5;	A n/a B n/a C 20 mg

...Expand

: 42882-03-1
1-bromo-6-nitropyrene

: 27973-29-1
1,6-dibromopyrene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With bromine In tetrachloromethane at 20℃; for 12h;

...Expand

: 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

Conditions	Yield
In dichloromethane at 20℃; for 1h; Overall yield = 97 %; Overall yield = 398 mg;

...Expand

: 10462-33-6
3,3'-dibromo-2,2'-diamino-1,1'-biphenyl

: 27973-29-1
1,6-dibromopyrene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 10h; Inert atmosphere; Reflux;	90%

1,6-Dibromopyrene Chemical Properties

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

1,6-Dibromopyrene Specification

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

Product Name

1,6-Dibromopyrene

Synthetic route

1,6-Dibromopyrene Chemical Properties

1,6-Dibromopyrene Specification

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