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(9-Phenyl-9H-carbazol-3-yl)boronic acid
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Name

(9-Phenyl-9H-carbazol-3-yl)boronic acid

 EINECS 691-972-0
CAS No. 854952-58-2 Density 1.2 g/cm3
PSA 45.39000 LogP 2.46350
Solubility Slightly soluble in water. Melting Point N/A
Formula C18H14BNO2 Boiling Point 466 °C at 760 mmHg
Molecular Weight 287.126 Flash Point 235.6 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 854952-58-2 (9-Phenyl-9H-carbazol-3-ylboronic acid) Hazard Symbols N/A
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;

Article Data 65

(9-Phenyl-9H-carbazol-3-yl)boronic acid Synthetic route

1153-85-1

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

121-43-7

Trimethyl borate

7732-18-5

water

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

7732-18-5

water

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

7732-18-5

water

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

7732-18-5

water

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

7732-18-5

water

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%

(9-Phenyl-9H-carbazol-3-yl)boronic acid 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

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