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4,4'-Bis(N-carbazolyl)-1,1'-biphenyl
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Name

4,4'-Bis(N-carbazolyl)-1,1'-biphenyl

 EINECS 627-757-5
CAS No. 58328-31-7 Density 1.19 g/cm3
PSA 9.86000 LogP 9.54780
Solubility N/A Melting Point 281-285 °C
Formula C36H24N2 Boiling Point 700.8 °C at 760 mmHg
Molecular Weight 484.6 Flash Point 377.6 °C
Transport Information N/A Appearance N/A
Safety 26-36/39 Risk Codes 37/38-41
Molecular Structure Molecular Structure of 58328-31-7 (4,4'-Bis(N-carbazolyl)-1,1'-biphenyl) Hazard Symbols IrritantXi
Synonyms

Carbazole,9,9'-(4,4'-biphenylylene)di- (6CI);4,4'-Bis(N-carbazole)biphenyl;4,4'-Bis(N-carbazolyl)biphenyl;4,4'-Bis(carbazol-9-yl)biphenyl;4,4'-Biscarbazolylbiphenyl;4,4'-Di(N-carbazole)-1,1'-biphenyl;4,4'-Di(N-carbazolyl)biphenyl;4,4'-N,N'-Dicarbazolylbiphenyl;CBP (dye);DCBP (chargetransfer agent);

Article Data 26

4,4'-Bis(N-carbazolyl)-1,1'-biphenyl Synthetic route

3001-15-8

4,4'-diiodobiphenyl

86-74-8

9H-carbazole

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
With copper(I) chloride; potassium carbonate In dimethyl sulfoxide at 140 - 170℃; for 4h;98%
With potassium carbonate; copper(l) chloride In dimethyl sulfoxide at 140 - 170℃; for 4h;98%
With copper(l) iodide; caesium carbonate; lithium chloride In N,N-dimethyl-formamide at 150℃; for 48h;92%
2050-68-2

4,4'-dichlorobiphenyl

86-74-8

9H-carbazole

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5℃; for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: 4,4'-dichlorobiphenyl With 2,6-bis(2,4,6-triisopropylphenyl)phenyl(dicyclohexylphosphine) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dodecane at 145℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;		98%
92-86-4

4-(4-bromophenyl)bromobenzene

86-74-8

9H-carbazole

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5 - 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-(4-bromophenyl)bromobenzene With PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 108 - 112℃; for 0.25h; Inert atmosphere;		97%
With 1-methyl-pyrrolidin-2-one; copper; potassium carbonate at 240℃; for 72h;55%
With iodine; copper; potassium carbonate Nitrobenzol;
With potassium carbonate In nitrobenzene for 72h; Reflux;
57102-42-8

N-(4-bromophenyl)carbazole

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
Stage #1: N-(4-bromophenyl)carbazole With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere;
Stage #2: With copper(l) cyanide In tetrahydrofuran; pentane at -78 - 25℃; Inert atmosphere;
Stage #3: In tetrahydrofuran; pentane at 25℃; for 3h; Inert atmosphere;		93%
2050-68-2

4,4'-dichlorobiphenyl

86-74-8

9H-carbazole

A

342638-54-4

3,3'-Bis(9H-carbozol-9-yl)-1,1'-biphenyl

B

1325751-60-7

9,9'-(biphenyl-3,4'-diyl)bis(9H-carbazole)

C

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
With potassium tert-butylate In toluene at 130 - 140℃; for 48h; Inert atmosphere; Autoclave; regioselective reaction;A 5%
B 2%
C 90%
92-86-4

4-(4-bromophenyl)bromobenzene

86-74-8

9H-carbazole

A

342638-54-4

3,3'-Bis(9H-carbozol-9-yl)-1,1'-biphenyl

B

1325751-60-7

9,9'-(biphenyl-3,4'-diyl)bis(9H-carbazole)

C

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
With potassium tert-butylate In toluene at 130 - 140℃; for 48h; Inert atmosphere; Autoclave; regioselective reaction;A 8.5%
B 4%
C 77%
13029-09-9

2,2'-dibromobiphenyl

92-87-5

p,p'-diaminobiphenyl

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
With (6-Dipp)PdCl2-SPhos; sodium t-butanolate In neat (no solvent) at 170℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere;76%
With caesium carbonate; L-proline; copper(l) chloride In dimethyl sulfoxide at 150℃; for 48h;32%
2915-43-7

4,4'-diazidobiphenyl

4688-76-0

2-Biphenylboronic acid

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; sodium carbonate In 1,4-dioxane at 80℃; for 12h; Schlenk technique;70%
1150-62-5

N-phenylcarbazole

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
With tungsten(VI) chloride In dichloromethane Inert atmosphere;61%
92-86-4

4-(4-bromophenyl)bromobenzene

74367-40-1

N-(trimethylsilyl)-9H-carbazole

58328-31-7

4,4'-bis(9H-carbazol-9-yl)biphenyl

Conditions
ConditionsYield
With tri-tert-butyl phosphine; caesium carbonate; cesium fluoride; tris-(dibenzylideneacetone)dipalladium(0); carbon dioxide In hexane at 100℃; under 93086.6 Torr; for 48h;47%

4,4'-Bis(N-carbazolyl)-1,1'-biphenyl Specification

The CAS register number of 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl is 58328-31-7. It also can be called as 4,4-N, N'-Dicarbazole-1,1'-biphenyl and the systematic name about this chemical is 9,9'-biphenyl-4,4'-diylbis(9H-carbazole). The molecular formula about this chemical is C36H24N2 and the molecular weight is 484.59. It belongs to the following product categories, such as Electronic; Electronic Chemicals; Carbazoles; Carbazoles (for Conduting Polymer Research); Electroluminescence; Functional Materials; Reagents for Conducting Polymer Research; White powder and so on. This chemical is stable under normal temperature and pressure. If you want to store it, please keep it in a colsed, cool and dry place, ans also keep away from light, you also need avoid contact with water.

Physical properties about 4,4'-Bis(N-carbazolyl)-1,1'-biphenyl are: (1)ACD/LogP: 11.93; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 11.93; (4)ACD/LogD (pH 7.4): 11.93; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 10000000; (8)ACD/KOC (pH 7.4): 10000000; (9)#H bond acceptors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 9.86Å2; (12)Index of Refraction: 1.697; (13)Molar Refractivity: 155.98 cm3; (14)Molar Volume: 404.8 cm3; (15)Polarizability: 61.83x10-24cm3; (16)Surface Tension: 49.5 dyne/cm; (17)Enthalpy of Vaporization: 102.58 kJ/mol; (18)Boiling Point: 700.8 °C at 760 mmHg; (19)Vapour Pressure: 1.73E-19 mmHg at 25°C.

Preparation: this chemical can be prepared by carbazole and 4,4'-dibromo-biphenyl. This reaction will need reagent K2CO3, copper bronze, 1-methyl-2-pyrrolidinone. The reaction time is 72 hour(s) with reaction temperature of 240 ℃. The yield is about 55%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to respiratory system and skin, it has risk of serious damage to the eyes. When you are using it, wear suitable protective clothing and eye / face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cccc3c1c2c(cccc2)n3c8ccc(c7ccc(n6c4ccccc4c5ccccc56)cc7)cc8
(2)InChI: InChI=1/C36H24N2/c1-5-13-33-29(9-1)30-10-2-6-14-34(30)37(33)27-21-17-25(18-22-27)26-19-23-28(24-20-26)38-35-15-7-3-11-31(35)32-12-4-8-16-36(32)38/h1-24H
(3)InChIKey: VFUDMQLBKNMONU-UHFFFAOYAG
(4)Std. InChI: InChI=1S/C36H24N2/c1-5-13-33-29(9-1)30-10-2-6-14-34(30)37(33)27-21-17-25(18-22-27)26-19-23-28(24-20-26)38-35-15-7-3-11-31(35)32-12-4-8-16-36(32)38/h1-24H
(5)Std. InChIKey: VFUDMQLBKNMONU-UHFFFAOYSA-N

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