Home Cart 0 Sign in  
X

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

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 18711-15-4
Chemical Structure| 18711-15-4
Chemical Structure| 18711-15-4
Structure of 18711-15-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 18711-15-4 ]

Related Doc. of [ 18711-15-4 ]

Alternatived Products of [ 18711-15-4 ]

Product Details of [ 18711-15-4 ]

CAS No. :18711-15-4 MDL No. :MFCD01971146
Formula : C8H3Cl2NO2 Boiling Point : -
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 Ų

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.

  • Upstream synthesis route of [ 18711-15-4 ]
  • Downstream synthetic route of [ 18711-15-4 ]

[ 18711-15-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 18711-11-0 ]
  • [ 18711-15-4 ]
YieldReaction ConditionsOperation in experiment
96% 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 50°C. 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 percent) was obtained as orange-colored solid: TLC Rf = 0.4 (EtOAc:n-hexane = 1:3); mp 228-230 ; 1H NMR (DMSO-d6) δ 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% at 0 - 90℃; for 1 h; 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, 96percent). TLC Rf= 0.4 (ethylacetate:n-hexane = 1 :3); mp 228-2300C;1H NMR (DMSO-d6)δ 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% 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, 96percent).
TLC Rf=0.4 (ethylacetate:n-hexane=1:3);
mp 228-230° C.;
1H NMR (DMSO-d6) δ 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, # 2, 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
  • 2
  • [ 75-87-6 ]
  • [ 626-43-7 ]
  • [ 18711-15-4 ]
Reference: [1] Patent: US6576656, 2003, B1,
  • 3
  • [ 626-43-7 ]
  • [ 18711-15-4 ]
Reference: [1] Helvetica Chimica Acta, 1919, vol. 2, p. 239
  • 4
  • [ 18711-15-4 ]
  • [ 20776-63-0 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydroxide; dihydrogen peroxide In water for 2 h; 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 (28percent 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, 82percent) 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) δ 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%
Stage #1: With sodium hydroxide; dihydrogen peroxide In water at 20℃; for 2 h;
Stage #2: With hydrogenchloride In water
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 percent 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 percent) 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) δ 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%
Stage #1: With sodium hydroxide; dihydrogen peroxide In water at 20℃; for 2 h;
Stage #2: With hydrogenchloride In water
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 percent 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, 82percent).TLC Rf= 0.1 (ethylacetate : n-hexane = 1:1); m.p. 188 - 189 °C;1HNMR (DMSO-de) δ 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%
Stage #1: With dihydrogen peroxide; sodium hydroxide In water at 20℃;
Stage #2: With hydrogenchloride In water
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 (28percent 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, 82percent).
TLC Rf=0.1 (ethylacetate: n-hexane=1:1);
m.p. 188-189° C.;
1H NMR (DMSO-d6) δ 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, # 2, 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
[7] Journal of Organic Chemistry, 1956, vol. 21, p. 171
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 18711-15-4 ]

Chlorides

Chemical Structure| 6344-05-4

[ 6344-05-4 ]

4-Chloroindoline-2,3-dione

Similarity: 0.98

Chemical Structure| 18711-13-2

[ 18711-13-2 ]

4,7-Dichloroindoline-2,3-dione

Similarity: 0.93

Chemical Structure| 6341-92-0

[ 6341-92-0 ]

6-Coroindoline-2,3-dione

Similarity: 0.91

Chemical Structure| 1677-48-1

[ 1677-48-1 ]

5,6-Dichloroindoline-2,3-dione

Similarity: 0.89

Chemical Structure| 7477-63-6

[ 7477-63-6 ]

7-Cloroindoline-2,3-dione

Similarity: 0.86

Amides

Chemical Structure| 6344-05-4

[ 6344-05-4 ]

4-Chloroindoline-2,3-dione

Similarity: 0.98

Chemical Structure| 18711-13-2

[ 18711-13-2 ]

4,7-Dichloroindoline-2,3-dione

Similarity: 0.93

Chemical Structure| 6341-92-0

[ 6341-92-0 ]

6-Coroindoline-2,3-dione

Similarity: 0.91

Chemical Structure| 1677-48-1

[ 1677-48-1 ]

5,6-Dichloroindoline-2,3-dione

Similarity: 0.89

Chemical Structure| 7477-63-6

[ 7477-63-6 ]

7-Cloroindoline-2,3-dione

Similarity: 0.86

Ketones

Chemical Structure| 6344-05-4

[ 6344-05-4 ]

4-Chloroindoline-2,3-dione

Similarity: 0.98

Chemical Structure| 18711-13-2

[ 18711-13-2 ]

4,7-Dichloroindoline-2,3-dione

Similarity: 0.93

Chemical Structure| 6341-92-0

[ 6341-92-0 ]

6-Coroindoline-2,3-dione

Similarity: 0.91

Chemical Structure| 1677-48-1

[ 1677-48-1 ]

5,6-Dichloroindoline-2,3-dione

Similarity: 0.89

Chemical Structure| 7477-63-6

[ 7477-63-6 ]

7-Cloroindoline-2,3-dione

Similarity: 0.86

Related Parent Nucleus of
[ 18711-15-4 ]

Indolines

Chemical Structure| 6344-05-4

[ 6344-05-4 ]

4-Chloroindoline-2,3-dione

Similarity: 0.98

Chemical Structure| 18711-13-2

[ 18711-13-2 ]

4,7-Dichloroindoline-2,3-dione

Similarity: 0.93

Chemical Structure| 6341-92-0

[ 6341-92-0 ]

6-Coroindoline-2,3-dione

Similarity: 0.91

Chemical Structure| 1677-48-1

[ 1677-48-1 ]

5,6-Dichloroindoline-2,3-dione

Similarity: 0.89

Chemical Structure| 7477-63-6

[ 7477-63-6 ]

7-Cloroindoline-2,3-dione

Similarity: 0.86