5599-70-2|1-Chloro-9H-carbazole| Ambeed

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Quality Control of [ 5599-70-2 ] Purity: 97% SDS Specification

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Product Details of [ 5599-70-2 ]

CAS No. :	5599-70-2
Formula :	C₁₄H₂₀O₁₀
M.W :	201.65
SMILES Code :	ClC1=CC=CC2=C1NC3=C2C=CC=C3
MDL No. :	MFCD18450171
InChI Key :	DBDCPKPHHCECLZ-UHFFFAOYSA-N
Pubchem ID :	12210469

Safety of [ 5599-70-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 5599-70-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	13
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	60.81
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	15.79 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.19
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	4.01
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.97
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.	3.37
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	4.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.55

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.3
Solubility	0.01 mg/ml ; 0.0000497 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.04
Solubility	0.0182 mg/ml ; 0.0000904 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
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	-5.58
Solubility	0.00053 mg/ml ; 0.00000263 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
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	Yes
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.	-4.68 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	0.0
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	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
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	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

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<2.0
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)	1.47

Application In Synthesis of [ 5599-70-2 ]

* 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 [ 5599-70-2 ]

[ 5599-70-2 ] Synthesis Path-Downstream 1~34

1
[ 53475-34-6 ]
[ 118-75-2 ]
[ 5599-70-2 ]

References: [1]Journal of the Chemical Society,1945,p. 530,532.

2
[ 5599-70-2 ]
[ 74-88-4 ]
[ 117909-12-3 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 173 - 175.

3
[ 67-72-1 ]
[ 111960-23-7 ]
[ 5599-70-2 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 794 - 799.

4
[ 56-23-5 ]
[ 86-74-8 ]
[ 5599-70-2 ]
[ 51035-14-4 ]
[ 82408-83-1 ]
[ 56995-05-2 ]

References: [1]Canadian Journal of Chemistry,1982,vol. 60,p. 945 - 956.

5
[ 67-72-1 ]
[ 86-74-8 ]
[ 5599-70-2 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 794 - 799.

6
[ 105598-33-2 ]
[ 64389-47-5 ]
[ 5599-70-2 ]
[ 2732-25-4 ]
[ 5599-71-3 ]
[ 86-74-8 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 173 - 175.

7
[ 90408-00-7 ]
[ 5599-70-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 429 - 434.

8
[ 86-74-8 ]
[ 5599-70-2 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 877 - 889.

9
[ 86-74-8 ]
[ 5599-70-2 ]
[ 2732-25-4 ]
[ 5599-71-3 ]
[ 58910-95-5 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 877 - 889.

10
[ 86-74-8 ]
[ 64389-47-5 ]
[ 5599-70-2 ]
[ 5599-71-3 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 877 - 889.
[2]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 877 - 889.

11
[ 105598-33-2 ]
[ 64389-47-5 ]
[ 5599-70-2 ]
[ 5599-71-3 ]
[ 86-74-8 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 877 - 889.
[2]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 877 - 889.

12
[ 5599-70-2 ]
[ 86-74-8 ]

References: [1]Photochemistry and Photobiology,1998,vol. 68,p. 640 - 645.

14
sodium-salt of/the/ 8-chloro-carbazole-1,3,6-trisulfonic acid [ No CAS ]
[ 5599-70-2 ]

References: [1]Patent: DE511021,1928, .
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 17,p. 723.

15
[ 86-74-8 ]
[ 5599-70-2 ]
[ 2732-25-4 ]

Yield	Reaction Conditions	Operation in experiment
8.3%; 87.7%	With 1,3-bis(1-adamantyl)imidazolium tetrafluoroborate; N-chloro-succinimide; camphor-10-sulfonic acid; In 1,4-dioxane; at 25℃; for 24.0h;	General procedure: A mixture of Acetylaniline (0.2 mmol), NCS (0.26 mmol), D-CSA (0.1 mmol) and 1,3-di(1-adamantl)imidazolium tetrafluoroborate (0.01 mmol) in dioxane (1 mL) wasstirred at room temperature (25 oC) under air atmosphere for 24h. The reactionmonitored by GC-MS. When the acetylaniline was consumed completely, the reactionmixture was quenched with saturated aq. NaHCO3 (4 mL). The resulting mixture wasextracted with EtOAc (4 mL x 3). The organic layer was washed with pure water (4ml x 3). The combined organic layer was dried over anhydrous Na2SO4, filtered andthe solvent was removed under reduced pressure to provide the crude product. Thepurification was performed by flash column chromatography on silica gel.

References: [1]Synlett,2015,vol. 26,p. 2831 - 2834.
[2]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 1583 - 1595.

16
1-(carbazol-9-yl)-2,4,6-trimethylpyridinium tetrafluoroborate [ No CAS ]
[ 108-75-8 ]
[ 5599-70-2 ]
[ 2732-25-4 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 8186 - 8195.

17
[ 86-74-8 ]
KOH [ No CAS ]
[ 5599-70-2 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 794 - 799.

18
[ 5599-70-2 ]
1,6-dichloro-N-methylcarbazole [ No CAS ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 173 - 175.

19
[ 87-65-0 ]
[ 5599-70-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 429 - 434.

20
[ 5599-70-2 ]
[ 23449-08-3 ]
C₃₃H₂₁ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 4.0h;Inert atmosphere; Reflux;	In a nitrogen atmosphereThe compound of formula IA (10 g, 50 mmol) and the compound of formula IB (19 g, 50 mmol)Was added to 250 ml of xylene and potassium hydroxide (5.6 g, 99 mmol), 1,10-phenanthroline (10 g, 19 mmol) was added with stirring.Then, by heating, copper iodide (2.8 g, 15 mmol) was slowly added under reflux. After the reaction was completed for about 4 hours, the reaction was terminated. After completion of the reaction, the temperature was lowered to room temperature, the salt was filtered through a filter, and the organic layer was distilled. Thereafter, the distillate was extracted twice with chloroform and water, and the organic layer was distilled off under reduced pressure Recrystallization with ethanol gave Intermediate 1 (19 g, 77percent).

References: [1]Patent: KR2017/116993,2017,A .Location in patent: Paragraph 0211; 0212; 0213.

21
[ 108-86-1 ]
[ 5599-70-2 ]
C₁₈H₁₂ClN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium phosphate; bis(tri-t-butylphosphine)palladium(0); for 3.0h;Reflux;	<strong>[5599-70-2]1-chloro-9H-carbazole</strong> 150.00 g (1.0 eq), bromobenzene 175.19 g (1.5 eq),315.79 g (2.0 eq) of K3PO4 and 1.90 g (0.005 eq) of Pd (t-Bu3P) 2 were dissolved in 1.85 L of toluene and refluxed and stirred. The solution was concentrated under reduced pressure for 3 hours. After that, it was completely dissolved in CHCl3, washed with water and decompressed again to remove about 50percent of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped, cooled, and filtered.This was subjected to column chromatography to obtain 150.82 g (yield: 73percent) of the compound represented by the formula 15-a-1.

References: [1]Patent: KR2017/113319,2017,A .Location in patent: Paragraph 0221; 0223; 0225; 0227-0228.

22
[ 5599-70-2 ]
C₂₄H₂₃BClNO₂ [ No CAS ]

References: [1]Patent: KR2017/113319,2017,A .

23
[ 5599-70-2 ]
(2-(2-hydroxypropan-2-yl)phenyl)boronic acid [ No CAS ]
C₂₁H₁₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium phosphate; bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; for 7.0h;Inert atmosphere; Heating;	Under nitrogen atmosphere, After <strong>[5599-70-2]1-chloro-9H-carbazole</strong> (50.0 g, 0.25 mol) and (2-(2-hydroxypropyl-2-yl)phenyl) boric acid (49.1 g, 0.27 mol) were dissolved in 500 mL of dioxane, K3PO4 (131.5 g, 0.62 mol) was added bis(tri-t-butylphosphine)palladium(0) (1.2 g, 2.5 mmol) and stirred with heating for 7 hours. After the temperature was lowered to room temperature, the aqueous layer was separated and removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized with ethyl acetate, and dried to produce the above intermediate B1 (61.2 g, yield 82percent).

References: [1]Patent: CN107915722,2018,A .Location in patent: Paragraph 0130-0133.

24
[ 5599-70-2 ]
(2-(2-hydroxypropan-2-yl)phenyl)boronic acid [ No CAS ]
7,7-dimethyl-7,12-dihydroindeno[1,2-a]carbazole [ No CAS ]

References: [1]Patent: CN107915722,2018,A .

25
[ 5599-70-2 ]
1-(2-chlorophenyl)-2-iodo-1H-benzo[d]imidazole [ No CAS ]
1-chloro-9-(1-(2-chlorophenyl)-1H-benzo[d]imidazol-2-yl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 12.0h;	1-Chloro-9H-carbazole (which is commercially available from multiple sources) is dissolved in dry DMF containing 1.5 eq. of potassium carbonate, 10 mol. percent of 18-crown-6 and 10 mol. percent of copper (I) iodide. The solution of 1-(2-chlorophenyl)-2-iodo-1H-benzo[d]imidazole in DMF is added dropwise, the reaction mixture is degassed, and then heated to 110° C. for 12 hrs. After completion, the reaction is cooled down to room temperature, diluted with LiCl 10percent aq. solution, and extracted with ethyl acetate. The organic solution is dried over sodium sulfate, filtered and evaporated. Chromatography on silica gel column provides pure 1-chloro-9-(1-(2-chlorophenyl)-1H-benzo[d]imidazol-2-yl)-9H-carbazole.

References: [1]Patent: US2018/315935,2018,A1 .Location in patent: Paragraph 0172.

26
[ 108-94-1 ]
[ 5599-70-2 ]