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[ CAS No. 919103-45-0 ] {[proInfo.proName]}

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Chemical Structure| 919103-45-0
Chemical Structure| 919103-45-0
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Product Details of [ 919103-45-0 ]

CAS No. :919103-45-0 MDL No. :MFCD09835633
Formula : C8H6INO Boiling Point : -
Linear Structure Formula :- InChI Key :UGEPVMQRMXPCMD-UHFFFAOYSA-N
M.W : 259.04 Pubchem ID :53418819
Synonyms :

Calculated chemistry of [ 919103-45-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.45
TPSA : 29.1 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) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 1.81
Log Po/w (WLOGP) : 1.21
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 2.82
Consensus Log Po/w : 1.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.265 mg/ml ; 0.00102 mol/l
Class : Soluble
Log S (Ali) : -2.04
Solubility : 2.36 mg/ml ; 0.00911 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.84
Solubility : 0.0373 mg/ml ; 0.000144 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.66

Safety of [ 919103-45-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 919103-45-0 ]

* 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 [ 919103-45-0 ]

[ 919103-45-0 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 919103-45-0 ]
  • [ 147-93-3 ]
  • [ 919103-46-1 ]
YieldReaction ConditionsOperation in experiment
20% Preparation 2: (2-Oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzoic acid CuI (40 mg, 0.05 mmol), potassium carbonate (1.66 g, 12 mmol), <strong>[919103-45-0]6-iodooxindole</strong> (as prepared in Preparation 1; 1.0 g, 4.0 mmol) and 2-mercapto-benzoic acid (0.62 g, 4.0 mmol) were added to a dry schlenk tube. The tube was evacuated and refilled with Ar(g) (3 times). 2-Propanol (5.0 mL) and ethylene glycol (0.5 mL, 8.0 mmol) were injected into the schlenk tube. The schlenk tube was sealed with a teflon valve and was heated to 80 C. and stirred for over 24 hours. Subsequently the reaction mixture was allowed to reach room temperature then diluted with EtOAc (10 mL) and water (10 mL). The mixture was acidified of to a pH=3-4 with the addition of 1 M HCl(aq) and the organics were separated and set aside. The aqueous phase was washed with additional EtOAc (10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo affording a yellow solid. The solid was then purified via flash silica gel chromatography (gradient eluant starting with 5% MeOH in CHCl3 increasing to 10% MeOH in CHCl3) affording the title compound as a pale yellow solid (0.228 g, 0.77 mmol, 20% yield).
  • 2
  • [ 99365-40-9 ]
  • [ 919103-45-0 ]
YieldReaction ConditionsOperation in experiment
84% With sodium iodide;copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; In 1,4-dioxane; at 110℃; for 24h; Preparation 1: 6-Iodooxindole A schlenk tube and stir bar were dried in an oven overnight and then were evacuated, filled with Ar(g) and cooled. The schlenk tube was charged with CuI (45 mg, 0.236 mmol, 5 mol %), 6-bromoxindole (1.0 g, 4.72 mmol), and NaI (1.42 g, 9.44 mmol). The schlenk tube was evacuated and backfilled with Ar(g) (3 times). Racemic trans-N,N'-dimethyl-1,2-cyclohexanediamine (74 muL, 0.472 mmol, 10 mol %) and anhydrous dioxane (4.72 mL) were added via syringe under Ar(g). The schlenk tube was sealed with a teflon valve and the suspension was stirred at 110 C. for 24 h. The reaction was then cooled to room temperature and 15% NH4OH(aq) (50 mL) was added to the reaction mixture while stirring. The suspension was allowed to stir for about 30 min after which the tan solid was vacuum filtered and dried affording 6-Iodooxindole in 84% yield (1.027 g, 3.96 mmol).
  • 3
  • [ 919103-50-7 ]
  • [ 919103-45-0 ]
  • [ 919103-51-8 ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate;copper(l) iodide; In ethylene glycol; isopropyl alcohol; at 80℃; for 24h; Step 4: N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide CuI (40 mg, 0.05 mmol), potassium carbonate (1.66 g, 12 mmol), <strong>[919103-45-0]6-iodooxindole</strong> (as prepared in Preparation 1; 0.5 g, 1.93 mmol) and N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-mercapto-benzamide (as prepared in step 3 above; 0.477 g, 1.93 mmol) were added to a dry schlenk tube. The tube was evacuated and refilled with Ar(g) (3 times). Isopropanol (3.0 mL) and ethylene glycol (0.250 mL) were injected into the schlenk tube. The schlenk tube was sealed with a teflon valve and was heated to 80 C. and stirred for over 24 hours. Subsequently the reaction mixture was allowed to reach room temperature then diluted with EtOAc (20 mL) and water (10 mL). The mixture was acidified with 1 M HCl(aq) and the organics were separated and set aside. The aqueous phase was washed with EtOAc (2×20 mL). The organic layers were combined, dried over silica gel, filtered and concentrated in vacuo affording a yellow solid. The solid was then purified via flash silica gel chromatography (gradient eluant 10 to 40% EtOAc in Hexanes) affording the title compound as a pale yellow solid (0.379 g, 1.01 mmol, 52% yield).
  • 4
  • [ 919103-45-0 ]
  • 3-{3-[1-(4-dimethylaminomethyl-phenylamino)-1-phenyl-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-propynoic acid ethylamide [ No CAS ]
  • 5
  • [ 919103-45-0 ]
  • [ 1537909-08-2 ]
  • 6
  • [ 919103-45-0 ]
  • [ 98-88-4 ]
  • [ 1535204-23-9 ]
YieldReaction ConditionsOperation in experiment
84.6% A nitrogen purged vessel is loaded with starting material 6-lodoindolinone (1 05kg,405mo1, 1,0 eq), catalyst 4-dimethylaminopyridine (DMAP) (2,52 kg) under argoncounter flow. Then triethylamine (145 kg, 3,5 eq) and solvent 2-methyltetrahydrofuran(605 kg) are charged to the vessel and the resulting solution is cooled to -15 00 to-S00 (preferentially -10C). Benzoylchloride (176,6 kg, 3,1 eq) is added to this mixture atan internal temperature of 100C to 50C within at least 30mm.The addition funnel is then flushed with 2-methyltetrahydrofuran (22 kg) and the reaction mixture is stirred for an additional hour at an internal temperature of 10 to 30C. If the content of starting material <strong>[919103-45-0]6-iodoindolinone</strong> is greater than 2,5 area%(H PLC), another portion of benzoylchloride (5,7 kg) is added to complete the reaction. If the content of starting material <strong>[919103-45-0]6-iodoindolinone</strong> is smaller than 2,5 area% (H PLC), lithium hydroxide (59,4 kg, 6,0 eq) is added in 5 differently sized portions (1st: 18,0 kg, 2?: 6,0 kg, 3: 6,0 kg, 41h: 15,0 kg, 5th: 14,4 kg) in a temperature controlled manner:After the two first portions, the mixture is stirred for 1 hour. After portion 3 and 4, the mixture is stirred for 30mm. After the last portion, the mixture is stirred for two hours. The reaction mixture (suspension) is then stirred for at least 12 hours at an internal temperature of 20 to 30 C. If the content of the non isolated intermediate of formula (V) is smaller than 0,5 area% (H PLC), water (525 L) is added and the mixture is heatedto an internal temperature of 60 to 7000 under stirring. Then the stirrer is switched off, the mixture is settled down and the phases are separated at an internal temperature of 60 to 70C. To the upper organic layer, water (525 L) is added and a second phase separation is carried out at an internal temperature of 60 to 70C. (Optionally, the mixture might be left stand at room temperature for up to 24 hours.) Then a partial solvent switch to tetrahydrofuran is carried out: Solvent is distilled off three times at a jacket temperature of 70C down to a residual volume of 390L followed by addition of tetrahydrofuran (1st: 233 kg, 2nd. 233 kg, 3rd. 117 kg). For crystallization, firstly, methanol (83 kg) is added.Optionally, the mixture might be left stand at room temperature for up to 24 hours. Secondly, water (112 L) is added at an internal temperature of 60 to 70C, followed by addition of conc. hydrochloric acid (156,2 kg). The addition funnel is flushed with water (20 L). The resulting suspension is cooled to 20 to 30C within at least 70mm (optionally, the mixture might be left stand at room temperature for up to 72 hours) and then to an internal temperature of minus 5 to 5 C within at least 30mm. The suspension is then centrifuged and the solid is washed with water (368 L) followed by methanol (112 kg) and dried at a jacket temperature of 50C until <= 1% of residual solvent is reached. The enol product of formula (IV) is obtained as solid in 84,6% yield.
84.6% [0496] A nitrogen purged vessel is loaded with starting material 6-Iodoindolinone (105 kg, 405 mol, 1.0 eq), catalyst 4-dimethylaminopyridine (DMAP) (2.52 kg) under argon counter flow. Then triethylamine (145 kg, 3.5 eq) and solvent 2-methyltetrahydrofuran (605 kg) are charged to the vessel and the resulting solution is cooled to -15 C. to -5 C. (preferentially -10 C.). Benzoylchloride (176.6 kg, 3.1 eq) is added to this mixture at an internal temperature of -10 C. to 50 C. within at least 30 min. [0497] The addition funnel is then flushed with 2-methyltetrahydrofuran (22 kg) and the reaction mixture is stirred for an additional hour at an internal temperature of 10 to 30 C. If the content of starting material <strong>[919103-45-0]6-iodoindolinone</strong> is greater than 2.5 area % (HPLC), another portion of benzoylchloride (5.7 kg) is added to complete the reaction. If the content of starting material <strong>[919103-45-0]6-iodoindolinone</strong> is smaller than 2.5 area % (HPLC), lithium hydroxide (59.4 kg, 6.0 eq) is added in 5 differently sized portions (1st: 18.0 kg, 2nd: 6.0 kg, 3rd: 6.0 kg, 4th: 15.0 kg, 5th: 14.4 kg) in a temperature controlled manner: After the two first portions, the mixture is stirred for 1 hour. After portion 3 and 4, the mixture is stirred for 30 min. After the last portion, the mixture is stirred for two hours. The reaction mixture (suspension) is then stirred for at least 12 hours at an internal temperature of 20 to 30 C. If the content of the non isolated intermediate of formula (V) is smaller than 0.5 area % (HPLC), water (525 L) is added and the mixture is heated to an internal temperature of 60 to 70 C. under stirring. Then the stirrer is switched off, the mixture is settled down and the phases are separated at an internal temperature of 60 to 70 C. To the upper organic layer, water (525 L) is added and a second phase separation is carried out at an internal temperature of 60 to 70 C. (Optionally, the mixture might be left stand at room temperature for up to 24 hours.) Then a partial solvent switch to tetrahydrofuran is carried out: Solvent is distilled off three times at a jacket temperature of 70 C. down to a residual volume of 390 L followed by addition of tetrahydrofuran (1st: 233 kg, 2nd: 233 kg, 3rd: 117 kg). For crystallization, firstly, methanol (83 kg) is added. [0498] Optionally, the mixture might be left stand at room temperature for up to 24 hours. Secondly, water (112 L) is added at an internal temperature of 60 to 70 C., followed by addition of conc. hydrochloric acid (156.2 kg). The addition funnel is flushed with water (20 L). The resulting suspension is cooled to 20 to 30 C. within at least 70 min (optionally, the mixture might be left stand at room temperature for up to 72 hours) and then to an internal temperature of minus 5 to 5 C. within at least 30 min. The suspension is then centrifuged and the solid is washed with water (368 L) followed by methanol (112 kg) and dried at a jacket temperature of 50 C. until <=1% of residual solvent is reached. The enol product of formula (IV) is obtained as solid in 84.6% yield.
0.88 g (7.23 mmol) 4-/V,/V-dimethylaminopyridine and 44.6 mL (101 .2 mmol) triethylamine are added successively to a suspension of 25.00 g (96.51 mmol) 6-iodo-1 ,3-dihydro-indol-2- one in 125.0 mL /V,/V-dimethylformamide. 27.81 g (197.8 mmol) benzoylchloride is added slowly at -10C to the reaction mixture and stirred for 2 h at -10C. After complete conversion (HPLC, Method A) 48.0 mL 10 M sodium hydroxide solution is added and stirred 1 h at room temperature. Then 350 mL water, 150 mL toluene and 80 mL cone, hydrochloric acid are successively added. The resulting precipitate is filtered, washed with water and toluene and dried at 50C in vacuo. [M+H]+: 364
0.88 g (7.23 mmol) 4-N,N-dimethylaminopyridine and 44.6 mL (101.2 mmol) triethylamine are added successively to a suspension of 25.00 g (96.51 mmol) <strong>[919103-45-0]6-iodo-1,3-dihydro-indol-2-one</strong> in 125.0 mL N,N-dimethylformamide. 27.81 g (197.8 mmol) benzoylchloride is added slowly at -10 C. to the reaction mixture and stirred for 2 h at -10 C. After complete conversion (HPLC, Method A) 48.0 mL 10 M sodium hydroxide solution is added and stirred 1 h at room temperature. Then 350 mL water, 150 mL toluene and 80 mL conc. hydrochloric acid are successively added. The resulting precipitate is filtered, washed with water and toluene and dried at 50 C. in vacuo.

  • 7
  • [ 919103-45-0 ]
  • [ 1535204-24-0 ]
  • 8
  • [ 919103-45-0 ]
  • [ 1535283-64-7 ]
  • 9
  • [ 919103-45-0 ]
  • [ 1535204-21-7 ]
  • 10
  • [ 919103-45-0 ]
  • C24H22IN3O [ No CAS ]
  • 11
  • [ 919103-45-0 ]
  • [ 1535204-25-1 ]
  • 13
  • [ 1573120-04-3 ]
  • [ 919103-45-0 ]
YieldReaction ConditionsOperation in experiment
62% With tin(II) chloride dihdyrate; In ethanol; water; at 70℃; for 1.5h; Preparation of 6-iodo-2-oxindole To a jacketed reactor, 2-(4-iodo-2-nitrobenzene)-dimethlymalonate (130 g) is charged at 20 C., followed by ethanol (600 mL). Then, to the above solution the first portion of SnCl2.2H2O (193.5 g) powder is added, and the resulting mixture is heated to 70 C. and stirred for 1 hour. The second portion of SnCl2.2H2O (193.5 g) is added, the mixture is stirred usually at least 0.5 hour until process monitor shows almost complete conversion. Then, heat the resulting mixture to 80 C. and add 36% aq. HCl solution (360 mL) during 0.5 hour. The mixture is stirred for at least 2.5 hours until process monitor shows almost complete conversion. Then, to the mixture water (550 mL) is added and the resulting mixture is cooled down to 20 C. Collect the solid by filtration and wash the solid with water (500 mL) to afford the crude 6-iodo-2-oxindole. Then, it is purified by crystallization with acetic acid (HOAc) (560 mL), and followed by washing with 3 N aq. HCl solution (480 mL) to afford the 6-iodo-2-oxindole in 62% yield and 99% HPLC purity (Rt=7.45 min). 1H NMR (400 MHz, DMSO) delta 10.42 (5, 1H), 7.29-7.27 (dd, J=8.0, 1.6 Hz, 1H,), 7.11 (d, J=1.6 Hz, 1H), 7.02-7.00 (d, J=8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 175.9, 145.3, 129.6, 126.4, 125.7, 117.4, 92.2, 35.4; MS (ESI): m/z 260.1 (M+1).
62% To a jacketed reactor, 2-(4-iodo-2-nitrobenzene)-dimethlymalonate (130 g) is charged at 20 C, followed by ethanol (600 mL). Then, to the above solution the first portion of SnCI2.2H20 (193.5 g) powder is added, and the resulting mixture is heated to 70 C and stirred for 1 hour. The second portion of SnCI2.2H20 (193.5 g) is added, the mixture is stirred usually at least 0.5 hour until process monitor shows almost complete conversion. Then, heat the resulting mixture to 80 C and add 36% aq. HCI solution (360 mL) during 0.5 hour. The mixture is stirred for at least 2.5 hours until process monitor shows almost complete conversion. Then, to the mixture water (550 mL) is added and the resulting mixture is cooled down to 20 C. Collect the solid by filtration and wash the solid with water (500 mL) to afford the crude 6-iodo-2-oxindole. Then, it is purified by crystallization with acetic acid (HOAc) (560 mL), and followed by washing with 3 N aq. HCI solution (480 mL) to afford the 6-iodo-2-oxindole in 62% yield and 99% HPLC purity (Rt = 7.45 min).1H NMR (400 MHz, DMSO) 510.42(S, 1 H), 7.29-7.27 (dd, J = 8.0, 1 .6Hz, 1 H, ), 7.1 1 (d, J = 1 .6 Hz, 1 H), 7.02-7.00 (d, J = 8.0 Hz, 1 H);13C NMR (100 MHz, CDCI3) delta 175.9, 145.3, 129.6, 126.4, 125.7, 1 17.4,92.2, 35.4; MS (ESI): m/z 260.1 (M+1 ).
  • 14
  • [ 1338507-93-9 ]
  • [ 919103-45-0 ]
YieldReaction ConditionsOperation in experiment
53% With tin(II) chloride dihdyrate; In ethanol; at 70℃; for 1.5h; To a jacketed reactor, N,N-dimethylacetamide (DMAc) (120 mE) and sodium ethylate (NaOEt) powder (12.1 g) is charged at 20 C. Diethylmalonate (28.8 g) is added dropwise into the above mixture while keeping internal temperature at around 10 C. Afier finishing addition, warm up the mixture to 20 C., and continue to stir for another 10 minutes. Then, 2-chloro-5-iodonitrobenzene (17 g) is added in one portion, and heat the mixture to 78 C. and stir for usually at least 2.5 hours until process monitor shows almost complete conversion. The resulting mixture is cooled down to 20 C., and it is quenched by 2 N cold aq. HC1 solution (180 mE). The bottom yellow oil was transferred to ajacket reactor with ethanol (92 mE) in it. Then, to the above solution the first portion of SnCl2.2H20 (30 g) powder is added, and the resulting mixture is heated to 70 C. and stirred for 1 hour. The second portion of SnCl2.2H20 (30 g) is added, the mixture is stirred usually at least 0.5 hour until process monitor shows almost complete conversion. Then, heat the resulting mixture to 80 C. and add 36% aq. HC1 solution (60 mE) during 0.5 hout The mixture is stirred for at least 2.5 hours until process monitor shows almost complete conversion. Then, to the mixture water (90 mE) is added and the resulting mixture is cooled down to 20 C. Collect the solid by filtration and wash the solid with water (250 mE) to afford the crude 6-iodo-2- oxindole. Then, it is purified by crystallization with acetic acid (HOAc) (110 mE), and followed by washing with 3 N aq. HC1 solution (80 mE) to afford the 6-iodo-2-oxindole in 53% yield and 99% HPEC purity (Rt=7.45 mm).10033] ?H NMR (400 MHz, DMSO) oe10.42 (5, 1H), 7.29-7.27 (dd, J=8.0, 1.6 Hz, 1H,), 7.11 (d, J=1.6 Hz, 1H), 7.02-7.00 (d, J=8.0 Hz, 1H); ?3C NMR (100 MHz, CDC13) oe 175.9,145.3, 129.6, 126.4, 125.7, 117.4, 92.2, 35.4; MS (ESI): mlz260.1 (M+1).
To a jacketed reactor, N,N-dimethylacetamide (DMAc) (120 mL) and soium ethylate (NaOEt) powder (12.1 g) is charged at 20 C. Diethylmalonate (28.8 g) is added dropwise into the above mixture while keeping internal temperature at around 10 C. After finishing addition, warm up the mixture to 20 C, and continue to stir for another 10 minutes. Then, 2-chloro-5- iodonitrobenzene (17 g) is added in one portion, and heat the mixture to 78 C and stir for usually at least 2.5 hours until process monitor shows almost complete conversion. The resulting mixture is cooled down to 20 C, and it is quenched by 2 N cold aq. HCI solution (180 mL). The bottom yellow oil was tranfered to a jaceket reactor with ethanol (92 mL) in it. Then, to the above solution the first portion of SnCI2.2H20 (30 g) powder is added, and the resulting mix- ture is heated to 70 C and stirred for 1 hour. The second portion of SnCI2.2H20 (30 g) is added, the mixture is stirred usually at least 0.5 hour until process monitor shows almost complete conversion. Then, heat the resulting mixture to 80 C and add 36% aq. HCI solution (60 mL) during 0.5 hour. The mixture is stirred for at least 2.5 hours until process monitor shows almost complete conversion. Then, to the mixture water (90 mL) is added and the resulting mix- ture is cooled down to 20 C. Collect the solid by filtration and wash the solid with water (250 mL) to afford the crude 6-iodo-2-oxindole. Then, it is purified by crystallization with acetic acid (HOAc) (1 10 mL), and followed by washing with 3 N aq. HCI solution (80 mL) to afford the 6- iodo-2-oxindole in 53% yield and 99% HPLC purity (Rt = 7.45 min).1H NMR (400 MHz, DMSO) 510.42(S, 1 H), 7.29-7.27 (dd, J = 8.0, 1 .6Hz, 1 H, ), 7.1 1 (d, J = 1 .6 Hz, 1 H), 7.02-7.00 (d, J = 8.0 Hz, 1 H);13C NMR (100 MHz, CDCI3) delta 175.9, 145.3, 129.6, 126.4, 125.7, 1 17.4,92.2, 35.4; MS (ESI): m/z 260.1 (M+1 ).
  • 16
  • [ 919103-45-0 ]
  • [ 2973-77-5 ]
  • C15H8Br2INO2 [ No CAS ]
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