[ CAS No. 5599-70-2 ] {[proInfo.proName]}

Name: 5599-70-2|1-Chloro-9H-carbazole|97%
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SKU: A167766
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Quality Control of [ 5599-70-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5599-70-2 ]

Product Details of [ 5599-70-2 ]

CAS No. :	5599-70-2	MDL No. :	MFCD18450171
Formula :	C₁₄H₂₀O₁₀	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DBDCPKPHHCECLZ-UHFFFAOYSA-N
M.W :	201.65	Pubchem ID :	12210469
Synonyms :

Calculated chemistry of [ 5599-70-2 ]

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 :	15.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.19
Log Po/w (XLOGP3) :	4.01
Log Po/w (WLOGP) :	3.97
Log Po/w (MLOGP) :	3.37
Log Po/w (SILICOS-IT) :	4.21
Consensus Log Po/w :	3.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.3
Solubility :	0.01 mg/ml ; 0.0000497 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.04
Solubility :	0.0182 mg/ml ; 0.0000904 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.58
Solubility :	0.00053 mg/ml ; 0.00000263 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.47

Safety of [ 5599-70-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 5599-70-2 ]
Downstream synthetic route of [ 5599-70-2 ]

[ 5599-70-2 ] Synthesis Path-Upstream 1~12

1
[ 86-74-8 ]
[ 5599-70-2 ]
[ 2732-25-4 ]

Yield	Reaction Conditions	Operation in experiment
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 h;	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.

Reference： [1] Synlett, 2015, vol. 26, # 20, p. 2831 - 2834
[2] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 7, p. 1583 - 1595

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

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 877 - 889
[2] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 877 - 889

3
[ 90408-00-7 ]
[ 5599-70-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 429 - 434

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

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 877 - 889
[2] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 877 - 889

5
[ 67-72-1 ]
[ 111960-23-7 ]
[ 5599-70-2 ]

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, # 4, p. 794 - 799

6
[ 67-72-1 ]
[ 86-74-8 ]
[ 5599-70-2 ]

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, # 4, p. 794 - 799

7
[ 86-74-8 ]
[ 5599-70-2 ]
[ 2732-25-4 ]
[ 5599-71-3 ]
[ 58910-95-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 877 - 889

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

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 877 - 889

9
[ 87-65-0 ]
[ 5599-70-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 429 - 434

10
[ 53475-34-6 ]
[ 118-75-2 ]
[ 5599-70-2 ]

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

11
[ 56-23-5 ]
[ 86-74-8 ]
[ 5599-70-2 ]
[ 51035-14-4 ]
[ 82408-83-1 ]
[ 56995-05-2 ]

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

12
[ 105598-33-2 ]
[ 64389-47-5 ]
[ 5599-70-2 ]
[ 2732-25-4 ]
[ 5599-71-3 ]
[ 86-74-8 ]

Reference： [1] Journal of Organic Chemistry, 1987, vol. 52, # 2, p. 173 - 175

[ 5599-70-2 ] Synthesis Path-Downstream 1~52

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

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

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

Reference： [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 ]

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

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

Reference： [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 ]

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

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

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

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

Reference： [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 ]

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

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

Reference： [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 ]

Reference： [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 ]

Reference： [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 ]

Reference： [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.

Reference： [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 ]

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

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

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

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

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

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

Reference： [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).

Reference： [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.

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

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

Reference： [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).

Reference： [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 ]

Reference： [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.

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

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