955964-73-5|2,7-Dibromo-9-(heptadecan-9-yl)-9H-carbazole| Ambeed

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Quality Control of [ 955964-73-5 ] Purity: 95% SDS Specification

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Product Details of [ 955964-73-5 ]

CAS No. :	955964-73-5
Formula :	C₂₉H₄₁Br₂N
M.W :	563.45
SMILES Code :	CCCCCCCCC(N1C2=C(C3=C1C=C(Br)C=C3)C=CC(Br)=C2)CCCCCCCC
MDL No. :	MFCD16619379
InChI Key :	HRUNMSCVUSIWQM-UHFFFAOYSA-N
Pubchem ID :	53400972

Safety of [ 955964-73-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 955964-73-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	32
Num. arom. heavy atoms	13
Fraction Csp3	0.59
Num. rotatable bonds	15
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	153.02
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	4.93 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	6.69
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	12.61
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	11.36
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	7.79
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	10.46
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	9.78

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-10.59
Solubility	0.0000000145 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-12.74
Solubility	0.0000000001 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-12.07
Solubility	0.0000000005 mg/ml ; 0.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Insoluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-0.78 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	2.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	1.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.17

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<3.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.39

Application In Synthesis of [ 955964-73-5 ]

* 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 [ 955964-73-5 ]

[ 955964-73-5 ] Synthesis Path-Downstream 1~24

1
[ 61676-62-8 ]
[ 955964-73-5 ]
[ 958261-51-3 ]

Yield	Reaction Conditions	Operation in experiment
70%		Compound f-5 (5.0 g, 9.0 mmol) into a round bottom flask in a vacuum caught after 4 Holding time Vacuum THF (150mL) into the dissolve. at -78 °C n-butyllithium (2.0M in Hexanes, 11.26mL) was slowly added after the mixture was stirred for two hours. 2 hours later, 2-isopropoxy -4,4,5,5- tetramethyl 1-1,3,2- Sabo dioxane was added to lane (5.52mL) slowly and stirred for 4 hours and allowed to react for 40 hours at room temperature. After completion of the reaction it was cooled with methanol and methylene chloride to remove the remaining moisture in the salt water over anhydrous magnesium sulfate (MgSO4), extract the organic layer and then rotary evaporated to end with ethyl acetate-hexane 1: 9 to 9 column with a solid-state to yield (heptadecane-9-yl)-2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl) -9Hcarbazole (compound F) (yield: 70percent ).

References: [1]Macromolecules,2012,vol. 45,p. 8658 - 8664.
[2]Patent: KR101495152,2015,B1 .Location in patent: Paragraph 0164; 0180-0181.
[3]Journal of Polymer Science, Part A: Polymer Chemistry,2012,vol. 50,p. 5011 - 5022.
[4]Journal of the American Chemical Society,2012,vol. 134,p. 19035 - 19042.
[5]New Journal of Chemistry,2011,vol. 35,p. 1327 - 1334.
[6]Polymer,2010,vol. 51,p. 3196 - 3202.

2
toluene-4-sulfonic acid 1-octyl-nonyl ester [ No CAS ]
[ 136630-39-2 ]
[ 955964-73-5 ]

Yield	Reaction Conditions	Operation in experiment
90%		9-Heptadecanyl-2,7-dibromocarbazole (9): 2,7-dibromo-9-H-carbazole (4 g, 12 mmol) and potassium hydroxide (0.84 g, 17.8 mmol) were solubilized in dry DMSO (40 mL). The reaction mixture was heated at 80 C for 1 h before adding dropwise a solution of 9-Heptadecane p-toluenesulfonate (6.4 g, 15.6 mmol) in 60 mL of dry DMSO. After cooling down at room temperature, the reaction mixture was poured into 300 mL of water and extracted three times with 100 mL of diethylether, dried over magnesium sulfate and the solvent was removed under vacuum. The white powder was purified by flash chromatography in cyclohexane to afford white crystals (yield: 90%). 1H NMR (400 MHz, CDCl3): delta (ppm) 7.5 (s, 2H); 7.27 (s, 2H); 7.12 (m, 2H), 4.48 (tt, J = 10.1, 5.1 Hz, 1H); 2.20 (m, 2H); 1.83 (m, 2H) 1.32-1.02 (m, 28H); 0.83 (t, J = 7.0 Hz, 6H). 13C NMR (100 MHz, CDCl3): delta (ppm) 125.61; 125.23; 120.43; 118.54; 111.70, 108.87, 56.43; 33.85; 31.89; 29.53; 29.43; 29.30; 26.94; 22.73; 14.20. HRMS (EI+, m/z) [M]+ calculated (%) for C29H41Br2N: 561.16057, found 561.16261.
78%	With potassium hydroxide; In dimethyl sulfoxide; for 24h;	After loading the compound f-2 (1g) To a round flask, place the compound 4-f (1.9g, 1.5eq). And after inserting the KOH (1g, 5eq) above, it is injected DMSO as a solvent. And then stirred for 24 hours, the organic layer was extracted with MC and the salt water to remove the remaining water over anhydrous magnesium sulfate and, after evaporation of the solvent was recrystallized from a MC and MeOH as a white solid 2,7-dibromo-9- (heptadecane and the -9-yl) -9H-carbazole (compound f-5) obtained. (Yield: 78%)

References: [1]Polymer,2017,vol. 119,p. 274 - 284.
[2]Macromolecules,2010,vol. 43,p. 9376 - 9383.
[3]Angewandte Chemie - International Edition,2019,vol. 58,p. 10179 - 10183.
Angew. Chem.,2019,vol. 131,p. 10285 - 10289,5.
[4]Patent: KR101495152,2015,B1 .Location in patent: Paragraph 0164; 0177-0178.
[5]Journal of the American Chemical Society,2012,vol. 134,p. 19035 - 19042.
[6]Journal of Polymer Science, Part A: Polymer Chemistry,2015,vol. 53,p. 2059 - 2068.
[7]Macromolecules,2012,vol. 45,p. 8658 - 8664.

3
[ 955964-73-5 ]
[ 73183-34-3 ]
[ 958261-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 87℃; for 4h;Inert atmosphere;	Add to the 500ml three-necked flask in turn2,7-dibromo-9- (heptadecane-9-yl) -9H- carbazole (5.61g, 0.01mol),Bis-boronic acid pinacolyl diborane (5.08 g, 0.02 mol), PdCl 2 (dppf) (0.05 g), CH 3 COOK (1.6 g, 0.016 mol),Under a nitrogen atmosphere, 1,4-dioxane (50 ml), which was deoxygenated with water, was added, and the mixture was refluxed at 87 C for 4 h.It was then cooled to room temperature, passed through a column (eluted with DCM) and evaporated to remove solvent.Add silica gel powder and sample through the column. A white solid was obtained.

References: [1]Macromolecules,2010,vol. 43,p. 9376 - 9383.
[2]Patent: CN106800527,2019,B .Location in patent: Paragraph 0047; 0053; 0063; 0064.

4
[ 955964-73-5 ]
[ 1313509-49-7 ]

References: [1]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 629 - 635.

5
[ 955964-73-5 ]
2,7-bis(bromomethyl)-9-(1-octylnonyl)-9H-carbazole [ No CAS ]

References: [1]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 629 - 635.

6
[ 955964-73-5 ]
[ 1313509-51-1 ]

References: [1]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 629 - 635.

7
[ 955964-73-5 ]
[ 68-12-2 ]
[ 1313509-47-5 ]

Yield	Reaction Conditions	Operation in experiment
82%		9-Heptadecanyl-2,7-diformylcarbazole (10): 9-Heptadecanyl-2,7-dibromocarbazole (3 g, 5.3 mmol) was solubilized in 130 mL of dry THF and was cooled at -78 °C. Then 16 mL (25.6 mmol) of a solution of n-butyl lithium was added dropwise. The reaction mixture was then heated up at 0 °C for 1 h and cooled down again at -78 °C. Then 6 mL of DMF was added and the reaction was mixed during 4 h at room temperature. The reaction mixture was then poured into 100 mL of cold and lightly acid water, filtered and washed with water. The crude yellow solid was then purified by flash chromatography two times, first in toluene and a second time in a mixture of heptane and ethyl acetate (80/20) to afford a yellow powder (yield: 82percent). 1H NMR (400 MHz, CDCl3): delta (ppm) 10.17 (s, 2H); 8.25 (s, 2H); 8.00 (d, J = 48.1 Hz, 2H); 7.72 (d, J = 8.0 Hz, 2H), 4.68 (tt, J = 10.2, 5.1 Hz, 1H); 2.25 (m, 2H); 1.92 (m, 2H) 1.26-1.09 (m, 28H); 0.80 (t, J = 7.0 Hz, 6H). 13C NMR (101 MHz, CDCl3): delta (ppm) 192.56; 121.28; 113.32; 112.66; 103.47; 57.28; 33.94; 31.83; 29.40; 29.38; 29.19; 26.94; 22.69; 14.16. FT-IR (ATR): nu = 2916, 2844, 1689, 1570, 1460, 1444, 1223, 1166, 992, 856, 803, 731 cm-1. HRMS (EI+, m/z) [M]+ calculated (percent) for C31H43NO2: 461.32938, found 461.32967.

References: [1]Polymer,2017,vol. 119,p. 274 - 284.
[2]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 629 - 635.

8
[ 955964-73-5 ]
[ 1373816-34-2 ]