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854952-58-2

Basic Information
CAS No.: 854952-58-2
Name: 9-Phenyl-9H-carbazol-3-ylboronic acid
Article Data: 65
Molecular Structure:
Molecular Structure of 854952-58-2 (9-Phenyl-9H-carbazol-3-ylboronic acid)
Formula: C18H14BNO2
Molecular Weight: 287.126
Synonyms: Boronic acid, B-(9-phenyl-9H-carbazol-3-yl)-;9-phenyl-9H-carbazol-3-yl-3-boronic acid;(9-phenyl)carbazole-3-boronic acid;
EINECS: 691-972-0
Density: 1.2 g/cm3
Boiling Point: 466 °C at 760 mmHg
Flash Point: 235.6 °C
Solubility: Slightly soluble in water.
PSA: 45.39000
LogP: 2.46350
Synthetic route
1153-85-1

3-bromo-9-phenyl-9H-carbazole

121-43-7

Trimethyl borate

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #3: water With hydrogenchloride In tetrahydrofuran Inert atmosphere;
90.2%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: Trimethyl borate at -78℃; Inert atmosphere;
Stage #3: water With hydrogenchloride for 0.5h; Inert atmosphere;
82.4%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1h;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 12h;
Stage #3: water With hydrogenchloride In tetrahydrofuran
81%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere;
Stage #3: water With hydrogenchloride at 20℃; for 0.5h;
67%
1153-85-1

3-bromo-9-phenyl-9H-carbazole

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h; Inert atmosphere;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 15h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 1h;
86%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 15h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃;
86%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Further stages.;
83%
1153-85-1

3-bromo-9-phenyl-9H-carbazole

121-43-7

Trimethyl borate

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h;
Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -80 - 20℃; for 15h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; for 1h;
86%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -80℃; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -80 - 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 1h;
86%
With hydrogenchloride; n-butyllithium; magnesium sulfate In tetrahydrofuran; hexane; chloroform80%
121-43-7

Trimethyl borate

29874-83-7

2-chloro-4-phenylquinazoline

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 2-chloro-4-phenylquinazoline With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: Trimethyl borate at -78℃; Inert atmosphere;
Stage #3: water With hydrogenchloride for 0.5h; Inert atmosphere;
82.4%
1153-85-1

3-bromo-9-phenyl-9H-carbazole

5419-55-6

Triisopropyl borate

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;
Stage #2: Triisopropyl borate In diethyl ether; hexane at -78℃;
Stage #3: water With hydrogenchloride In diethyl ether; hexane at 20℃;
82%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;
Stage #2: Triisopropyl borate In diethyl ether; hexane at -78 - 20℃;
Stage #3: water With hydrogenchloride In diethyl ether; hexane
1153-85-1

3-bromo-9-phenyl-9H-carbazole

5419-55-6

Triisopropyl borate

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;
Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 0.5h; Inert atmosphere;
80%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at -10℃; Inert atmosphere;
70%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 12h;
Stage #3: With water In tetrahydrofuran; hexane
67.33%
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;
Stage #2: Triisopropyl borate In diethyl ether; hexane at -78 - 20℃;
5419-55-6

Triisopropyl borate

57103-20-5

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

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: Triisopropyl borate; 3,6-dibromo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -70 - -60℃; for 1h; Inert atmosphere;
Stage #2: water With hydrogenchloride In tetrahydrofuran; hexane at -20℃; for 1h; Solvent; Inert atmosphere;
77%
121-43-7

Trimethyl borate

502161-03-7

3-iodo-9-phenyl-9H-carbazole

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 3-iodo-9-phenyl-9H-carbazole With magnesium In tetrahydrofuran at 75 - 80℃; for 12h;
Stage #2: Trimethyl borate In tetrahydrofuran at 0℃; for 5h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 2h; Cooling;
76%
Stage #1: 3-iodo-9-phenyl-9H-carbazole With water; magnesium In tetrahydrofuran at 75 - 80℃; for 12h;
Stage #2: Trimethyl borate In tetrahydrofuran at -20 - 0℃; for 5h;
Stage #3: With hydrogenchloride In tetrahydrofuran at 0 - 20℃; for 2h;
76%
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 1h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane
51%
5419-55-6

Triisopropyl borate

502161-03-7

3-iodo-9-phenyl-9H-carbazole

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - -5℃; Inert atmosphere;
Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -45℃; for 2h;
Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene at 20℃;
70%
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - -5℃; for 1h; Inert atmosphere;
Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -45℃; for 2h;
Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene at 20℃; Product distribution / selectivity;
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane; toluene at -45 - -5℃; for 1h; Inert atmosphere;
Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -45℃; for 2h; Inert atmosphere;
Stage #3: With hydrogenchloride In diethyl ether; hexane; water; toluene at 20℃; Inert atmosphere;
Stage #1: 3-iodo-9-phenyl-9H-carbazole With n-butyllithium In hexane; toluene at -45 - -5℃; for 1h; Inert atmosphere;
Stage #2: Triisopropyl borate In hexane; toluene at -45℃; for 2h;
Stage #3: With hydrogenchloride In hexane; water; toluene at 20℃;
1153-85-1

3-bromo-9-phenyl-9H-carbazole

1776-66-5

triisopropylborane

854952-58-2

N-phenyl-9H-carbazol-3-boronic acid

Conditions
ConditionsYield
Stage #1: 3-bromo-9-phenyl-9H-carbazole With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;
Stage #2: triisopropylborane In diethyl ether; hexane at -78 - 20℃;
Stage #3: water With hydrogenchloride In diethyl ether; hexane
70%
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    9-Phenyl-9H-carbazol-3-ylboronic acid

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    Product Name: 9-Phenyl-9H-carbazol-3-ylboronic acid CAS: 854952-58-2 MF: C18H14BNO2 MW: 287.12 EINECS: 691-972-0 Mol File: 854952-58-2.mol 9-Phenyl-9H-carbazol-3-ylboronic acid Structure 9-Phenyl-9H-carbazol-3-ylboronic acid Chemi

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  • 9-Phenyl-9H-carbazol-3-ylboronic acid CAS: 854952-58-2

  • Casno:

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    Product name: 9-Phenyl-9H-Carbazol-3-Ylboronic Acid CAS No.:854952-58-2 Molecule Formula:C18H14BNO2 Molecule Weight:287.12 Purity: 99.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard TESTIN

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Specification

The systematic name of B-(9-phenyl-9H-carbazol-3-yl)boronic acid is (9-phenylcarbazol-3-yl)boronic acid. With the CAS registry number 854952-58-2, it is also named as (9-Phenyl-9H-carbazol-3-yl)boronic acid. In addition, its molecular formula is C18H14BNO2 and its molecular weight is 287.12.

The other characteristics of B-(9-phenyl-9H-carbazol-3-yl)boronic acid can be summarized as: (1)ACD/LogP: 5.57; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.57; (4)ACD/LogD (pH 7.4): 5.55; (5)ACD/BCF (pH 5.5): 10031.88; (6)ACD/BCF (pH 7.4): 9689.51; (7)ACD/KOC (pH 5.5): 25452.1; (8)ACD/KOC (pH 7.4): 24583.47; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 45.39 Å2; (13)Index of Refraction: 1.638; (14)Molar Refractivity: 85.79 cm3; (15)Molar Volume: 238.6 cm3; (16)Polarizability: 34.01×10-24cm3; (17)Surface Tension: 47.9 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 235.6 °C; (20)Enthalpy of Vaporization: 76.67 kJ/mol; (21)Boiling Point: 466 °C at 760 mmHg; (22)Vapour Pressure: 1.74E-09 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: B(c1ccc2c(c1)c3ccccc3n2c4ccccc4)(O)O
(2)InChI: InChI=1/C18H14BNO2/c21-19(22)13-10-11-18-16(12-13)15-8-4-5-9-17(15)20(18)14-6-2-1-3-7-14/h1-12,21-22H
(3)InChIKey: JWJQEUDGBZMPAX-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C18H14BNO2/c21-19(22)13-10-11-18-16(12-13)15-8-4-5-9-17(15)20(18)14-6-2-1-3-7-14/h1-12,21-22H
(5)Std. InChIKey: JWJQEUDGBZMPAX-UHFFFAOYSA-N