[ CAS No. 18711-15-4 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 18711-15-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 18711-15-4 ]

SDS Specification

Alternatived Products of [ 18711-15-4 ]

Product Details of [ 18711-15-4 ]

CAS No. :	18711-15-4	MDL No. :	MFCD01971146
Formula :	C₈H₃Cl₂NO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	CGCVHJCZBIYRQC-UHFFFAOYSA-N
M.W :	216.02	Pubchem ID :	251908
Synonyms :		Chemical Name :	4,6-Dichloroisatin

Calculated chemistry of [ 18711-15-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.18
TPSA :	46.17 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.0
Log Po/w (XLOGP3) :	1.97
Log Po/w (WLOGP) :	1.56
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	2.78
Consensus Log Po/w :	1.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.76
Solubility :	0.374 mg/ml ; 0.00173 mol/l
Class :	Soluble
Log S (Ali) :	-2.57
Solubility :	0.588 mg/ml ; 0.00272 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.02
Solubility :	0.0208 mg/ml ; 0.0000962 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 18711-15-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 18711-15-4 ]

* 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 [ 18711-15-4 ]

[ 18711-15-4 ] Synthesis Path-Downstream 1~14

1
[ 18711-15-4 ]
[ 626-43-7 ]
4,6-dichloro-3-(3,5-dichloro-phenylimino)-indolin-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1956,vol. 21,p. 171

2
[ 18711-15-4 ]
[ 20776-63-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide; dihydrogen peroxide; In water; for 2h;	At room temperature, to a solution of the intermediate I-2 (5.0 g, 23.1 mmol) prepared by the above peparation example I(2) in 75 mL 1N NaOH (aq) was added portionwise hydrogen peroxide (28% v/v, 10 mL). The reaction mixture was filtered after stirring for 2 hours to remove insoluble dark brown solid. The filterate was then carefully acidified to pH 2 by conc. hydrochloric acid. The formed yellow precipitates were collected, washed with water, and dried in vacuo. The objective compound (3.90 g, 82%) was obtained as ivory-colored solid by recrystalization from benzene: TLC Rf=0.1 (EtOAc:n-hexane=1:1); m.p. 188-189 C.; 1H NMR (DMSO-d6) delta 6.76 (d, J=1.9 Hz, 1H, ArH), 6.85 (d, J=1.9 Hz, 1H, ArH); MS (EI) m/e 206 [M+], 162 [M+-CO2].
82%		3) Intermediate I-3; 2-amino-4,6-dichloro benzoic acid; At room temperature, to a solution of the intermediate I-2 (5.0 g, 23.1 mmol) prepared by the above peparation example I(2) in 75 mL 1N NaOH (aq) was added portionwise hydrogen peroxide (28 % v/v, 10 mL). The reaction mixture was filtered after stirring for 2 hours to remove insoluble dark brown solid. The filterate was then carefully acidified to pH 2 by conc. hydrochloric acid. The formed yellow precipitates were collected, washed with water, and dried in vacuo. The objective compound (3.90 g, 82 %) was obtained as ivory-colored solid by recrystalization from benzene: TLC Rf = 0.1 (EtOAc:n-hexane = 1:1); m.p. 188 - 189 C; 1H NMR (DMSO-d6) delta 6.76 (d, J = 1. 9 Hz, 1H, ArH), 6.85 (d, J = 1. 9 Hz, 1H, ArH); MS(EI) m/e 206[M+], 162[M+-CO2].
82%		Step 3: Preparation of 2-amino-4,6-dichlorobenzoic acidTo a solution of 4,6-dihloro-lH-indole-2,3-dione (5.0 g, 23.1 mmol) in 75 ml of 1 N <n="28"/>NaOH was partially added hydrogen peroxide (28 % v/v, 10 ml) at room temperature. After stirring the mixture for 2 hours, an insoluble dark brown solid was removed by filtration. The filtrate was acidified with a cone, hydrochloric acid to a pH of 2. The yellow precipitate thus formed was harvested, washed with distilled water, and dried in a vacuum. Recrystallization in benzene produced the title compound as an ivory solid (3.90 g, 82%).TLC Rf= 0.1 (ethylacetate : n-hexane = 1:1); m.p. 188 - 189 C;1HNMR (DMSO-de) delta 6.76 (d, IH5J= 1.9 Hz5 ArH), 6.85 (d, IH5J= 1.9 Hz5 ArH);MS(EI) m/e 206 [M+], 162 [M+-CO2].

82%

Step 3 Preparation of 2-amino-4,6-dichlorobenzoic acid To a solution of 4,6-dihloro-1H-indole-2,3-dione (5.0 g, 23.1 mmol) in 75 ml of 1 N NaOH was partially added hydrogen peroxide (28% v/v, 10 ml) at room temperature. After stirring the mixture for 2 hours, an insoluble dark brown solid was removed by filtration. The filtrate was acidified with a cone, hydrochloric acid to a pH of 2. The yellow precipitate thus formed was harvested, washed with distilled water, and dried in a vacuum. Recrystallization in benzene produced the title compound as an ivory solid (3.90 g, 82%). TLC Rf=0.1 (ethylacetate: n-hexane=1:1); m.p. 188-189 C.; 1H NMR (DMSO-d6) delta 6.76 (d, 1H, J=1.9 Hz, ArH), 6.85 (d, 1H, J=1.9 Hz, ArH); MS (EI) m/e 206 [M+], 162 [M+-CO2].

Reference： [1]Patent: US2006/84676,2006,A1 .Location in patent: Page/Page column 7
[2]Patent: EP1650190,2006,A1 .Location in patent: Page/Page column 10
[3]Patent: WO2008/4716,2008,A1 .Location in patent: Page/Page column 25-26
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 738 - 743
[5]Patent: US2009/203708,2009,A1 .Location in patent: Page/Page column 8
[6]Journal of the American Chemical Society,1956,vol. 78,p. 1251,1254

3
[ 18711-11-0 ]
[ 18711-15-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sulfuric acid; at 0 - 90℃;	2) Intermediate I-2; 4,6-dichloro-1H-indole-2,3-dione; The Intermediate I-1 (10.0 g, 42.9 mmol) prepared by the above preparation example I(1) was slowly added to conc. sulfuric acid (50 mL) in an ice bath. At this moment, the temperature of the reaction mixture was maintained below 50C. After complete the addition, the solution of dark color was heated for 10 minutes at 90 C. After cooling down the resultant to room temperature, the reactant was poured into ice having 10 times of the reactant volume, and was vigorously stirred for 1 hour. The insoluble solid formed in the above procedure was collected, washed with water, dried in vacuo, and the objective compound (8.90 g, 96 %) was obtained as orange-colored solid: TLC Rf = 0.4 (EtOAc:n-hexane = 1:3); mp 228-230 ; 1H NMR (DMSO-d6) delta 6.97 (d, J = 1.8 Hz, 1H, ArH), 7.32 (d, J = 1.8 Hz, 1H, ArH), 11.42 (br s, 1H, NH); MS (EI) m/e 216[M+], 188 [M+-CO2], 160.
96%	With sulfuric acid; at 0 - 90℃; for 1h;	Step 2: Preparation of 4,6-dichloro-lH-indole-2,3-dione N-(3,5-dicUorophenyl)-2-hydroxyimino-acetamide (10.0 g, 42.9 mmol), prepared in step 1, was slowly added to cone, sulfuric acid (50 ml) in an ice bath. At this time, the reaction mixture was required to be maintained at 5O0C or less. Following completion of the addition, the turbid solution was heated to 9O0C for 1 hour with stirring. The resulting reaction mixture was cooled to room temperature and then added to 10 volumes of crushed ice blocks and stirred for 1 hour. The insoluble solid thus formed was harvested, washed with distilled water and dried in a vacuum to give the title compound as an orange solid (8.90 g, 96%). TLC Rf= 0.4 (ethylacetate:n-hexane = 1 :3); mp 228-2300C;1H NMR (DMSO-d6)delta 6.97 (d, IH, J= 1.8 Hz, ArH), 7.32 (d, IH, J= 1.8 Hz, ArH), 11.42 (br s, IH5NH);MS(EI) m/e 216 [M+], 188 [M+-CO2], 160.
96%	With sulfuric acid; at 50 - 90℃;Cooling with ice;	Step 2 Preparation of 4,6-dichloro-1H-indole-2,3-dione N-(3,5-dichlorophenyl)-hydroxyimino-acetamide (10.0 g, 42.9 mmol), prepared in step 1, was slowly added to cone, sulfuric acid (50 ml) in an ice bath. At this time, the reaction mixture was required to be maintained at 50 C. or less. Following completion of the addition, the turbid solution was heated to 90 C. for 1 hour with stirring. The resulting reaction mixture was cooled to room temperature and then added to 10 volumes of crushed ice blocks and stirred for 1 hour. The insoluble solid thus formed was harvested, washed with distilled water and dried in a vacuum to give the title compound as an orange solid (8.90 g, 96%). TLC Rf=0.4 (ethylacetate:n-hexane=1:3); mp 228-230 C.; 1H NMR (DMSO-d6) delta 6.97 (d, 1H, J=1.8 Hz, ArH), 7.32 (d, 1H, J=1.8 Hz, ArH), 11.42 (br s, 1H, NH); MS (EI) m/e 216 [M+], 188 [M+-CO2], 160.

Reference： [1]Patent: EP1650190,2006,A1 .Location in patent: Page/Page column 10
[2]Patent: WO2008/4716,2008,A1 .Location in patent: Page/Page column 25
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 738 - 743
[4]Patent: US2009/203708,2009,A1 .Location in patent: Page/Page column 8
[5]Helvetica Chimica Acta,1919,vol. 2,p. 239

4
[ 623-73-4 ]
[ 18711-15-4 ]
Diazo-(4,6-dichloro-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-acetic acid ethyl ester [ No CAS ]