[ CAS No. 741293-42-5 ] {[proInfo.proName]}

Name: 741293-42-5|3,6-Dibromo-9-(4-(tert-butyl)phenyl)-9H-carbazole|99%
Brand: Ambeed
SKU: A360961
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Quality Control of [ 741293-42-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 741293-42-5 ]

Product Details of [ 741293-42-5 ]

CAS No. :	741293-42-5	MDL No. :	MFCD12024283
Formula :	C₂₂H₁₉Br₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JIWBCHGVZITSFJ-UHFFFAOYSA-N
M.W :	457.20	Pubchem ID :	59557273
Synonyms :

Calculated chemistry of [ 741293-42-5 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	19
Fraction Csp3 :	0.18
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	115.45
TPSA :	4.93 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.5
Log Po/w (XLOGP3) :	8.05
Log Po/w (WLOGP) :	7.61
Log Po/w (MLOGP) :	6.47
Log Po/w (SILICOS-IT) :	6.69
Consensus Log Po/w :	6.66

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-8.18
Solubility :	0.00000304 mg/ml ; 0.0000000067 mol/l
Class :	Poorly soluble
Log S (Ali) :	-8.01
Solubility :	0.00000449 mg/ml ; 0.0000000098 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.43
Solubility :	0.000000169 mg/ml ; 0.0000000004 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.09

Safety of [ 741293-42-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 741293-42-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 741293-42-5 ]

[ 741293-42-5 ] Synthesis Path-Downstream 1~21

1
[ 57103-13-6 ]
[ 741293-42-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 12.0h;Inert atmosphere;	9-(4-tert-butylphenyl)-9H-carbazole (4.0 g, 13.4 mmol), N-bromosuccinimide (7.0 g, 40.0 mmol) was placed in a reaction under a nitrogen atmosphere. In a tube, 45 mL of DMF was introduced in three portions and stirred at room temperature for 12 hours. After completion of the reaction, the reaction solution was dissolved in ethyl acetate, washed with water several times, and then evaporated to remove excess solvent. It was separated by a chromatography column (petroleum ether / ethyl acetate = 20:1).A pale yellow powder of 4.8 g was obtained in a yield of 80%.

Reference： [1]Organic Letters,2005,vol. 7,p. 5361 - 5364
[2]Patent: CN109293637,2019,A .Location in patent: Paragraph 0051; 0053
[3]New Journal of Chemistry,2019,vol. 43,p. 16629 - 16638

2
[ 741293-42-5 ]
[ 486-25-9 ]
[ 871018-06-3 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 5361 - 5364

3
[ 741293-42-5 ]
[ 76-86-8 ]
9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran;	EXAMPLE 1 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (Hereinafter Referred to as CzSi) and Synthesis Thereof CzSi: 9-(4-tert-butylphenyl)-3,6-dibromo-carbazole (1.8 g, 4 mmol) in THF (150 mL) were treated with n-BuLi (7.5 ml, 12 mmol) at -78 C. and quenched with a solution of chlorotriphenylsilane (3.54 g, 12 mmol) in THF (50 mL). The desired product was purified by column chromatography, eluding with CHCl3/Hexane (1/4) to provide the product as a white solid. (1.2 g, 35%). CzSi: m.p. 354 C. (DSC); IR (neat) ν 2960, 2359, 1681, 1428, 1260, 1025, 801, 699, 512 cm-1; 1H NMR (CDCl3, 400 MHz) δ 8.21 (s, 2H), 7.61-7.55 (m, 16H), 7.49-7.41 (m, 2H), 7.44-7.40 (m, 8H), 7.37-7.34 (m, 12H) 1.42 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ 150.1, 141.5, 136.0, 134.4, 134.0, 133.4, 129.0, 128.5, 127.4, 126.3, 126.1, 123.5, 122.7, 109.5, 35.1, 31.7; MS (m/z, FAB+) 815 (4); HRMS (m/z, FAB+) Calcd for C58H49NSi2 815.3404, found 815.3403; Anal. Calcd. For C58H49NSi2: C, 85.35; H, 6.05. Found: C, 85.10; H, 6.07.

Reference： [1]Patent: US2007/262704,2007,A1

4
[ 3972-65-4 ]
[ 741293-42-5 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 5361 - 5364

5
[ 86-74-8 ]
KOH [ No CAS ]
[ 741293-42-5 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 5361 - 5364

6
[ 741293-42-5 ]
[ 164461-18-1 ]
[ 1289558-36-6 ]

Reference： [1]Organic electronics,2011,vol. 12,p. 541 - 546

7
[ 741293-42-5 ]
C₄₇H₅₅BBrN [ No CAS ]

Reference： [1]Macromolecules,2011,vol. 44,p. 5961 - 5967

8
[ 741293-42-5 ]
C₃₂H₃₂BBr₂N [ No CAS ]

Reference： [1]Macromolecules,2011,vol. 44,p. 5961 - 5967

9
[ 741293-42-5 ]
[ 1066-45-1 ]
[ 1314589-25-7 ]

Reference： [1]Macromolecules,2011,vol. 44,p. 5961 - 5967

10
[ 741293-42-5 ]
[ 123324-71-0 ]
3-bromo-6,9-bis(4-(tert-butyl)phenyl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate; In toluene; at 90℃; for 24.0h;Inert atmosphere;	9-(4-tert-butylphenyl)-3,6-dibromo-9H-carbazole (3.0 g, 9.25 mmol), 1-tert-butyl-4-phenylboronic acid (4.0 g, 22.4 mmol), Pd(PPh3)4 (0.9g, 0.78mmol), TBAB (2mg, 0.005mmol) was placed in the reaction tube, pumped three times with a double-row tube, K2CO3 (30mL, 2mol / L) was placed in the reaction tube, added 80 mL of deoxygenated toluene was reacted at 90 C for 24 h under a nitrogen atmosphere. After completion of the reaction, the substrate was extracted three times with dichloromethane, and the excess solvent was evaporated.Separation by chromatography (petroleum ether / ethyl acetate = 10:1).A white powder of 2.4 g was obtained in a yield of 60%.

Reference： [1]Patent: CN109293637,2019,A .Location in patent: Paragraph 0051; 0054
[2]New Journal of Chemistry,2019,vol. 43,p. 16629 - 16638

11
[ 86-74-8 ]
[ 741293-42-5 ]

Reference： [1]Patent: CN109293637,2019,A
[2]New Journal of Chemistry,2019,vol. 43,p. 16629 - 16638

12
[ 35779-04-5 ]
[ 741293-42-5 ]

Reference： [1]Patent: CN109293637,2019,A
[2]New Journal of Chemistry,2019,vol. 43,p. 16629 - 16638

13
[ 741293-42-5 ]
3,9-bis(4-tert-butylphenyl)-6-pyrimidinyl-2-yl-9H-carbazole [ No CAS ]

Reference： [1]Patent: CN109293637,2019,A

14
[ 741293-42-5 ]
3,9-bis(4-(tert-butyl)phenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [ No CAS ]

Reference： [1]Patent: CN109293637,2019,A
[2]New Journal of Chemistry,2019,vol. 43,p. 16629 - 16638

15
[ 741293-42-5 ]
3,9-bis(4-tert-butylphenyl)-6-pyrimidinyl-5-yl-9H-carbazole [ No CAS ]

Reference： [1]Patent: CN109293637,2019,A

16
[ 741293-42-5 ]
2,5-bis(6,9-bis(4-(tert-butyl)phenyl)-9H-carbazol-3-yl)pyrazine [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 16629 - 16638

17
[ 741293-42-5 ]
C₃₆H₃₄BrN₃ [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 16629 - 16638

18
[ 741293-42-5 ]
9-(5-(6,9-bis(4-(tert-butyl)phenyl)-9H-carbazol-3-yl)pyrazin-2-yl)-3,6-bis(4-(tert-butyl)phenyl)-9H-carbazole [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 16629 - 16638

19
[ 741293-42-5 ]
N,N-(4,4-azanediylbis(4,1-phenylene))diheptanamide [ No CAS ]
C₇₄H₉₁N₇O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃; for 24.0h;Inert atmosphere;	3,6-dibromo-9-(4-tert-butylphenyl)-9H-carbazole (2g, 4.4mmol),P(t-Bu)3 (0.05 g, 0.22 mmol) and Pd2(dba)3 (0.12 g, 0.13 mmol)and toluene (30 mL)After dissolving it, it is filled with nitrogen. N,N-(4,4-azanediylbis(4,1-phenylene))diheptanamide (4.7g, 11mmol) and NaOtBu (1.27g, 13.2mmol) were added to the reaction mixture and stirred at 100C for 24 hours.After completion of the reaction, extraction is performed with MC and water. After removing residual moisture with MgSO4, purification is performed by column chromatography using EA:Hex to obtain an organic compound (Yield: 1.85g, 37%) of the following [Formula 11].

Reference： [1]Patent: KR2021/97497,2021,A .Location in patent: Paragraph 0213-0220

20
[ 741293-42-5 ]
[ 73852-19-4 ]
[ 2829924-34-5 ]

Yield	Reaction Conditions	Operation in experiment
70.5 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 90℃; Inert atmosphere; Darkness;	3 Example 3: Synthesis of compound M1 Compound M1 is the preparation step of 3,6-bis(3,5-bis(trifluoromethyl)phenyl)-9-(4-(tert-butyl)phenyl)-9H carbazole: 3,6- Dibromo-9-(4-tert-butylphenyl)-9H-carbazole (2 mmol, 0.914 g), 3,5-bis(trifluoromethyl)-phenylboronic acid (5 mmol, 1.29 g), K2CO3(8mmol, 1.10g), Pd(PPh3)4(0.1mmol, 0.12g), placed in a 50ml two-necked flask that was protected from light under a nitrogen atmosphere, exhausted three times with a double-row pipe, and injected a deoxygenated mixture Solvent (toluene:ethanol:water=10:1:2) 20ml, react at 90°C for 24h.After the reaction, the reaction solution was extracted with water, and then extracted three times with saturated brine and dichloromethane. The organic solvent in the lower layer was dried over anhydrous sodium sulfate, silica gel powder was added, and the excess solvent was removed by rotary evaporation.Separation by column chromatography (petroleum ether:ethyl acetate=12:1) gave 1.02 g of a white solid with a yield of 70.5%.

Reference： [1]Current Patent Assignee: NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS - CN114957092, 2022, A Location in patent: Paragraph 0042; 0047-0048

21
[ 741293-42-5 ]
[ 61676-62-8 ]
[ 1282616-11-8 ]

Yield	Reaction Conditions	Operation in experiment
90 %	Stage #1: 3,6-dibromo-9-(4-tert-butylphenyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃;

Reference： [1]Wang, Junting; Zheng, Aibin; Xiang, Yuren; Liu, Junzhi [Journal of the American Chemical Society, 2023]

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[ CAS No. 741293-42-5 ] {[proInfo.proName]}

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[ 741293-42-5 ] Synthesis Path-Downstream 1~21

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