2,7-Dibromo-9,9-diphenylfluororene supplier

Name
2,7-Dibromo-9,9-diphenylfluororene
EINECS 1533716-785-6
CAS No. 186259-63-2
Article Data13
CAS DataBase
Density 1.548 g/cm³
Solubility
Melting Point 279-281 °C
Formula C₂₅H₁₆Br₂
Boiling Point 520.3 °C at 760 mmHg
Molecular Weight 476.21
Flash Point 311.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,7-Dibromo-9,9-diphenyl-9H-fluorene;
PSA 0.00000
LogP 7.57470

Synthetic route

: 591-50-4
iodobenzene

: 16433-88-8
2,7-dibromo-9H-fluorene

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide for 5h; Sonication;	98%

: 132717-37-4
2,7-dibromo-(9-phenyl-9H-fluoren-9-ol)

: 71-43-2
benzene

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid at 80℃; for 6h; Reflux;	93%
With trifluorormethanesulfonic acid at 80℃; for 6h; Friedel-Crafts reaction;	88%
With trifluorormethanesulfonic acid at 50 - 80℃; for 6h; Inert atmosphere; Schlenk technique;	70%

: 20302-14-1
9,9-diphenylfluorene

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
With bromine; acetic acid In chloroform for 1h; Inert atmosphere; Reflux;	90%

: (4,4'-dibromo-biphenyl-2-yl)-diphenyl-methanol

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 100℃; for 1h;	89%

: 14348-75-5
2,7-dibromofluorene-9-one

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 3 h / Heating 2: conc. H2SO4 / 3 h View Scheme
Multi-step reaction with 2 steps 1: 90 percent / diethyl ether / Heating 2: 88 percent / CF3SO3H / 6 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1.1: magnesium / diethyl ether / 4 h / Reflux 1.2: 12 h / Reflux 2.1: trifluorormethanesulfonic acid / Heating View Scheme

: phenylmagnesium bromide

[(4-methoxy-1,3-η3-cyclohexenyl)PdCl]2: [(4-methoxy-1,3-η3-cyclohexenyl)PdCl]2

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 3 h / Heating 2: conc. H2SO4 / 3 h View Scheme

: methyl 4,4'-dibromo-[1,1'-biphenyl]-2-carboxylate

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / tetrahydrofuran; hexane / 17 h / -78 - 20 °C 2: 89 percent / H2SO4; AcOH / 1 h / 100 °C View Scheme

: 591-51-5
phenyllithium

[Ru(η3-CH2CHCH2)(η5-C5Me5)(η2-t-BuNC(Ph)=Nt-Bu)](1+)*PF6(1-): [Ru(η3-CH2CHCH2)(η5-C5Me5)(η2-t-BuNC(Ph)=Nt-Bu)](1+)*PF6(1-)

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / tetrahydrofuran; hexane / 17 h / -78 - 20 °C 2: 89 percent / H2SO4; AcOH / 1 h / 100 °C View Scheme

: phenylmagnesium bromide

antimony trichloride: antimony trichloride

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / diethyl ether / Heating 2: 88 percent / CF3SO3H / 6 h / 80 °C View Scheme

: 108-86-1
bromobenzene

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / diethyl ether / 4 h / Reflux 1.2: 12 h / Reflux 2.1: trifluorormethanesulfonic acid / Heating View Scheme

: 86-73-7
9H-fluorene

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / 1,2-propylene cyclic carbonate / 3 h / Reflux 2: chromium(VI) oxide; acetic acid / 1 h / 120 °C 3: iodine; magnesium / diethyl ether 4: trifluorormethanesulfonic acid View Scheme
Multi-step reaction with 4 steps 1.1: bromine / chloroform / 20 h / 0 - 20 °C / Darkness; Inert atmosphere; Schlenk technique 2.1: potassium dichromate; acetic acid / 6 h / 120 °C / Inert atmosphere; Schlenk technique 3.1: magnesium; iodine / tetrahydrofuran / Schlenk technique; Inert atmosphere 3.2: Reflux; Inert atmosphere; Schlenk technique 4.1: trifluorormethanesulfonic acid / 6 h / 50 - 80 °C / Inert atmosphere; Schlenk technique View Scheme

Yield

Multi-step reaction with 4 steps
1: N-Bromosuccinimide / 1,2-propylene cyclic carbonate / 3 h / Reflux
2: chromium(VI) oxide; acetic acid / 1 h / 120 °C
3: iodine; magnesium / diethyl ether
4: trifluorormethanesulfonic acid
View Scheme

Multi-step reaction with 4 steps
1.1: bromine / chloroform / 20 h / 0 - 20 °C / Darkness; Inert atmosphere; Schlenk technique
2.1: potassium dichromate; acetic acid / 6 h / 120 °C / Inert atmosphere; Schlenk technique
3.1: magnesium; iodine / tetrahydrofuran / Schlenk technique; Inert atmosphere
3.2: Reflux; Inert atmosphere; Schlenk technique
4.1: trifluorormethanesulfonic acid / 6 h / 50 - 80 °C / Inert atmosphere; Schlenk technique
View Scheme

: 16433-88-8
2,7-dibromo-9H-fluorene

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: chromium(VI) oxide; acetic acid / 1 h / 120 °C 2: iodine; magnesium / diethyl ether 3: trifluorormethanesulfonic acid View Scheme
Multi-step reaction with 3 steps 1.1: potassium dichromate; acetic acid / 6 h / 120 °C / Inert atmosphere; Schlenk technique 2.1: magnesium; iodine / tetrahydrofuran / Schlenk technique; Inert atmosphere 2.2: Reflux; Inert atmosphere; Schlenk technique 3.1: trifluorormethanesulfonic acid / 6 h / 50 - 80 °C / Inert atmosphere; Schlenk technique View Scheme
Multi-step reaction with 3 steps 1: potassium permanganate / 3 h / 20 °C / Inert atmosphere 2: tetrahydrofuran / 1 h / Inert atmosphere; Reflux 3: sulfuric acid / 16 h / Inert atmosphere; Reflux View Scheme

: 108-86-1
bromobenzene

: 14348-75-5
2,7-dibromofluorene-9-one

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C 1.2: 4 h / -78 °C 2.1: trifluorormethanesulfonic acid / 6 h / 80 °C / Reflux View Scheme

: 486-25-9
9-fluorenone

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; methanesulfonic acid / chloroform 2: sulfuric acid / tetrahydrofuran; benzene View Scheme

: 14348-75-5
2,7-dibromofluorene-9-one

: 100-58-3
phenylmagnesium bromide

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
With sulfuric acid In tetrahydrofuran; benzene

: 14348-75-5
2,7-dibromofluorene-9-one

: 591-51-5
phenyllithium

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
Friedel-Crafts Alkylation;

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 2,7-diiodo-9,9-diphenylfluorene

Conditions

Conditions	Yield
Stage #1: 2,7-dibromo-9,9-diphenyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: With iodine In tetrahydrofuran at 20℃; for 2h;	92%

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 1066-54-2
trimethylsilylacetylene

: C35H34Si2

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 20 - 70℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	92%

: 885665-22-5
9,9-diphenyl-7-trimethylsilylfluorenyl-2-boronic acid

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 885665-24-7
7,7'-bis(trimethylsilyl)-ter(9,9-diphenylfluorene)

Conditions

Conditions	Yield
With potassium carbonate; triphenylphosphine; palladium diacetate In methanol; toluene at 75℃; Suzuki cross-coupling;	86%

: 89415-43-0
(4-aminophenyl)boronic acid

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 4,4'-(9,9-diphenyl-9H-fluorene-2,7-diyl)dianiline

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; potassium carbonate In tetrahydrofuran at 80℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	86%

: 90-30-2
N-phenyl-1-naphthylamine

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: N,N'-di-naphthalen-1-yl-9,9,N,N'-tetraphenyl-9H-fluorene-2,7-diamine

Conditions

Conditions	Yield
With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 4h;	85%

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 684243-16-1
{4-[bis(2,4,6-trimethylphenyl)boranyl]phenyl}boronic acid

: 1498411-24-7
2,7-bis(4-(dimesitylboryl)phenyl)-9,9-diphenylfluorene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux; Inert atmosphere;	83%

: 866181-29-5
C20H13N3

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C65H40N6

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene for 8h; Heating;	82%

: 75-77-4
chloro-trimethyl-silane

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 885665-21-4
2-bromo-9,9-diphenyl-7-trimethylsilylfluorene

Conditions

Conditions	Yield
Stage #1: 2,7-dibromo-9,9-diphenyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 2h;	81%

: C20H13NS2

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C65H40N2S4

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 1h; Inert atmosphere;	78.9%

: 2‐{[1,1'‐biphenyl]‐2‐yl}‐4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 2,7-di(biphenyl-2-yl)-9,9-diphenyl-9H-fluorene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 24h; Suzuki Coupling; Inert atmosphere; Schlenk technique;	75%

: 205-25-4
benzo[c]carbazole

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C41H26BrN

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; Inert atmosphere;	74%

: 1205-64-7
3-Methyldiphenylamine

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 9,9,N,N'-tetraphenyl-N,N'-di-m-tolyl-9H-fluorene-2,7-diamine

Conditions

Conditions	Yield
With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 6h;	69%

: C24H23NO

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C73H60N2O2

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 105℃; for 24h; Inert atmosphere;	66.8%

: 7-N,N-diphenylamino-9,9-diphenylfluorenyl-2-boronic acid

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 2,7''-bis(diphenylamino)-7,2',7',2''-ter(9,9-diphenylfluorene)

Conditions

Conditions	Yield
With potassium carbonate; triphenylphosphine; palladium diacetate In methanol; toluene at 75℃; Suzuki cross-coupling;	65%

: C28H26BN3O3

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C81H64N6O2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene at 105℃; for 24h; Inert atmosphere;	63.3%

: 227003-50-1
4-butyl-N-(4-butylphenyl)aniline

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 1564287-40-6
7-bromo-N,N-bis(4-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere;	63%

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C27H18O2

Conditions

Conditions	Yield
Stage #1: 2,7-dibromo-9,9-diphenyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 3h;	63%
Stage #1: 2,7-dibromo-9,9-diphenyl-9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 3h;	60%

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 98-80-6
phenylboronic acid

: C31H21Br

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; for 2h; Inert atmosphere; Reflux;	62%

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 371193-08-7
9,9-dihexylfluorene-2-boronic acid

: 1106670-17-0
TFP

Conditions

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 75℃; for 24h; Suzuki coupling;	59%

: 1227040-87-0
4-(1,2,2-triphenylvinyl)phenylboronic acid

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 9,9-diphenyl-2,7-bis(4-(1,2,2-triphenylvinyl)phenyl)fluorene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Suzuki Coupling; Reflux; Inert atmosphere;	56%

: 952431-30-0
N-[1,1"-biphenyl]-4-yl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-[1,1-biphenyl]-4-amine

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C85H60N2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 115℃; for 14h; Inert atmosphere;	52%

: 122-39-4
diphenylamine

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

A: 2-bromo-7-diphenylamino-9,9-diphenylfluorene

B: C49H36N2

Conditions

Conditions	Yield
With tris-(o-tolyl)phosphine; sodium t-butanolate; palladium diacetate In toluene at 110℃; for 24h;	A 45% B 25%

...Expand

: 86-74-8
9H-carbazole

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C37H24BrN

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 33h; Inert atmosphere;	41%

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: 551951-04-3
3,6-bis(3,6-di-tert-butylcarbazol-N-yl)carbazole

: 1610059-35-2
C129H124N6

Conditions

Conditions	Yield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; 18-crown-6 ether; potassium carbonate at 180℃; for 48h;	35%

: 2350-01-8
4-aminotriphenylamine

: 90-11-9
1-Bromonaphthalene

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C81H58N4

Conditions

Conditions	Yield
Stage #1: 4-aminotriphenylamine; 2,7-dibromo-9,9-diphenyl-9H-fluorene With potassium carbonate; copper In nitrobenzene at 180℃; for 6h; Stage #2: 1-Bromonaphthalene In nitrobenzene for 18h;	32%

...Expand

: 32316-92-0
naphthalene-2-boronic acid

: 186259-63-2
2,7-dibromo-9,9-diphenyl-9H-fluorene

: C45H30

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In water; toluene for 2h; Inert atmosphere; Reflux;	16%

2,7-Dibromo-9,9-diphenylfluororene Specification

The 2,7-Dibromo-9,9-diphenylfluororene is an organic compound with the formula C₂₅H₁₆Br₂. The systematic name of this chemical is 2,7-dibromo-9,9-diphenyl-9H-fluorene. With the CAS registry number 186259-63-2, it is also named as 9H-fluorene, 2,7-dibromo-9,9-diphenyl-. The product's categories are Fluorene Derivatives; Electronic Chemicals.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 7.80; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.8; (4)ACD/LogD (pH 7.4): 7.8; (5)ACD/BCF (pH 5.5): 501784.44; (6)ACD/BCF (pH 7.4): 501784.44; (7)ACD/KOC (pH 5.5): 418795.16; (8)ACD/KOC (pH 7.4): 418795.16; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: Å²; (13)Index of Refraction: 1.693; (14)Molar Refractivity: 117.96 cm³; (15)Molar Volume: 307.5 cm³; (16)Polarizability: 46.76×10^-24 cm³; (17)Surface Tension: 55.3 dyne/cm; (18)Density: 1.548 g/cm³; (19)Flash Point: 311.1 °C; (20)Enthalpy of Vaporization: 76.34 kJ/mol; (21)Boiling Point: 520.3 °C at 760 mmHg; (22)Vapour Pressure: 2.08E-10 mmHg at 25°C.

People can use the following data to convert to the molecule structure.
1. SMILES:Brc3ccc4c1ccc(Br)cc1C(c2ccccc2)(c4c3)c5ccccc5
2. InChI:InChI=1/C25H16Br2/c26-19-11-13-21-22-14-12-20(27)16-24(22)25(23(21)15-19,17-7-3-1-4-8-17)18-9-5-2-6-10-18/h1-16H
3. InChIKey:AJYDOCCGNIBJBY-UHFFFAOYAD
4. Std. InChI:InChI=1S/C25H16Br2/c26-19-11-13-21-22-14-12-20(27)16-24(22)25(23(21)15-19,17-7-3-1-4-8-17)18-9-5-2-6-10-18/h1-16H
5. Std. InChIKey:AJYDOCCGNIBJBY-UHFFFAOYSA-N

Product Name

2,7-Dibromo-9,9-diphenylfluororene

Synthetic route

2,7-Dibromo-9,9-diphenylfluororene Specification

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