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Basic Information
CAS No.: 628336-95-8
Name: 9-HEXYL-3,6-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9H-CARBAZOLE
Molecular Structure:
Molecular Structure of 628336-95-8 (9-HEXYL-3,6-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9H-CARBAZOLE)
Formula: C30H43B2NO4
Molecular Weight: 503.298
Density: 1.06±0.1 g/cm3(Predicted)
Melting Point: 155.0 to 159.0 °C
Boiling Point: 587.6±43.0 °C(Predicted)
PSA: 41.85000
LogP: 5.97320
Related products
Synthetic route
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3,6-dibromo-9-hexyl-9H-carbazole

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bis(pinacol)diborane

628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Conditions
ConditionsYield
With potassium acetate; palladium dichloride In N,N-dimethyl-formamide at 110℃; for 24h;72%
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 85℃; for 12h; Inert atmosphere;60%
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 85℃; for 12h;59.6%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;
With potassium acetate; Pd(II)(dppf) In N,N-dimethyl-formamide for 12h; Miyaura Borylation Reaction; Inert atmosphere; Reflux; Sealed tube;
150623-72-6

3,6-dibromo-9-hexyl-9H-carbazole

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2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Conditions
ConditionsYield
Stage #1: 3,6-dibromo-9-hexyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 2h;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃;		64%
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

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3,6-diiodo-9-hexyl-9H-carbazole

628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,4-dioxane at 90℃; Inert atmosphere;44%
6825-20-3

3,6-dibromo-9H-carbazole

628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrabutylammomium bromide; potassium hydroxide / toluene; water
2: palladium dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h / 110 °C
View Scheme
111-25-1

1-bromo-hexane

628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrabutylammomium bromide; potassium hydroxide / toluene; water
2: palladium dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h / 110 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 48 h / 20 °C
2.1: N-Bromosuccinimide / chloroform / 40 °C
3.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 12 h / 85 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 48 h / 20 °C
2.1: N-Bromosuccinimide / chloroform / 12 h / 40 °C
3.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere
View Scheme
86-74-8

9H-carbazole

628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 48 h / 20 °C
2.1: N-Bromosuccinimide / chloroform / 40 °C
3.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 12 h / 85 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C
1.2: 48 h / 20 °C
2.1: N-Bromosuccinimide / chloroform / 12 h / 40 °C
3.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere
View Scheme
4041-21-8

N-hexylcarbazole

628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / chloroform / 12 h / 40 °C
2: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere
View Scheme
4701-17-1

5-bromo-2-thiophencarboxaldehyde

628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

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5,5’-(9-hexyl-9H-carbazole-3,6-diyl)bis(thiophene-2-carbaldehyde)

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 24h;77%
628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

(6R,6'R,8R,8'R)-3,3'-(4-bromopyridine-2,6-diyl)bis(7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline)

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Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene; tert-butyl alcohol at 80℃; for 48h; Schlenk technique;43%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene; tert-butyl alcohol at 80℃; for 48h; Inert atmosphere; Sealed tube;43%
628336-95-8

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

1519104-49-4

C26H24BrNS2

1519104-41-6

C70H67N3S4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;23%
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