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3652-90-2

Basic Information
CAS No.: 3652-90-2
Name: 2-Bromo-9H-carbazole
Article Data: 64
Cas Database
Molecular Structure:
Molecular Structure of 3652-90-2 (2-Bromo-9H-carbazole)
Formula: C12H8BrN
Molecular Weight: 246.106
Synonyms: 9H-Carbazole, 2-bromo-;2-Bromocarbazole;
EINECS: 807-979-0
Density: 1.617 g/cm3
Melting Point: 253.0 to 257.0 °C
Boiling Point: 409.228 °C at 760 mmHg
Flash Point: 201.294 °C
Solubility: N/A
Appearance: N/A
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 15.79000
LogP: 4.08360
Synthetic route

2-bromo-9-(pyrimidin-2-yl)-9H-carbazole

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
With N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water; copper(l) chloride; sodium t-butanolate In dimethyl sulfoxide at 110℃; for 24h; Schlenk technique; Inert atmosphere;99%
35450-34-1

4'-bromo-2-nitrobiphenyl

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
With triphenylphosphine In 1,2-dichloro-benzene at 170℃; for 12h; Inert atmosphere;89%
With triethyl phosphite In 1,2-dichloro-benzene at 80 - 150℃; Inert atmosphere;75%
Stage #1: 4'-bromo-2-nitrobiphenyl With triethyl phosphite at 160℃; for 2h;
Stage #2: With hydrogenchloride In water for 1h; Reflux;
67.6%

2-bromo-9H-carbazole

2-bromo-9H-carbazole

Conditions
ConditionsYield
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; potassium bromide In 1,4-dioxane at 130℃; for 16h; Inert atmosphere;83%

Conditions
ConditionsYield
With triethylphosphine for 12h; Reflux;82.4%
With triphenylphosphine In 1,2-dichloro-benzene at 200℃;77%
With triphenylphosphine In 1,2-dichloro-benzene Inert atmosphere; Reflux;77%
1-bromo-3-nitrosobenzene

1-bromo-3-nitrosobenzene

88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 20℃; regioselective reaction;80%

2-azido-4'-bromo-1,1'-biphenyl

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
In tetrahydrofuran for 4h; Solvent; Inert atmosphere; Irradiation;80%

2-bromo-9-(pyrimidin-2-yl)-9H-carbazole

A

3652-90-2

2-bromo-9H-carbazole

B

2-hydroxy-9-(2-pyrimidinyl)carbazole

Conditions
ConditionsYield
With N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water; copper(l) chloride; sodium hydroxide In dimethyl sulfoxide at 110℃; for 24h; Schlenk technique; Inert atmosphere;A 74%
B 26%

3-bromodibenzo[b,d]iodol-5-ium trifluoromethanesulfonate

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
With sodium azide; copper(I) thiophene-2-carboxylate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere; Schlenk technique;63%
With sodium azide; copper(I) thiophene-2-carboxylate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere; Schlenk technique;63%
62532-98-3

4'-bromo-[1,1'-biphenyl]-2-amine

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper diacetate; Trimethylacetic acid In 1-methyl-pyrrolidin-2-one at 120℃; for 12h;33%
Multi-step reaction with 2 steps
1.1: acetic acid; sodium nitrite / water / 1 h / 0 °C
1.2: Sandmeyer Reaction / 1 h / 0 - 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 4 h / Inert atmosphere; Irradiation
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite / water; tetrahydrofuran / 1 h / 0 - 5 °C
1.2: 20 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 20 °C
3.1: copper(I) thiophene-2-carboxylate; triphenylphosphine; sodium azide; sodium hydrogencarbonate / N,N-dimethyl acetamide / 12 h / 100 °C / Inert atmosphere; Schlenk technique
View Scheme
78863-99-7

7-bromo-2,3,4,9-tetrahydro-1H-carbazole

3652-90-2

2-bromo-9H-carbazole

Conditions
ConditionsYield
With chloranil; xylene
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Specification

1.Introduction of 2-Bromocarbazole

The 2-Bromocarbazole with the CAS number 3652-90-2 is also called 9H-Carbazole, 2-bromo-. The systematic name is 2-bromo-9H-carbazole. Its molecular formula is C12H8BrN. This chemical is a kind of organics. It should be stored in dry and cool environment.

2.The properties of the 2-Bromocarbazole

(1)ACD/LogP: 4.59; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4; (4)ACD/LogD (pH 7.4): 4; (5)ACD/BCF (pH 5.5): 1527; (6)ACD/BCF (pH 7.4): 1527; (7)ACD/KOC (pH 5.5): 6614; (8)ACD/KOC (pH 7.4): 6614; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 15.79 Å2; (13)Index of Refraction: 1.784; (14)Molar Refractivity: 64.061 cm3; (15)Molar Volume: 152.172 cm3; (16)Polarizability: 25.396×10-24cm3; (17)Surface Tension: 60.866 dyne/cm; (18)Enthalpy of Vaporization: 63.566 kJ/mol; (19)Vapour Pressure: 0 mmHg at 25°C.

3.Structure descriptors of 2-Bromocarbazole

(1)SMILES: Brc1ccc2c3ccccc3nc2c1
(2)InChI: InChI=1/C12H8BrN/c13-8-5-6-10-9-3-1-2-4-11(9)14-12(10)7-8/h1-7,14H
(3)InChIKey: PJRGCJBBXGNEGD-UHFFFAOYAK