[ CAS No. 919103-45-0 ]

Name: 919103-45-0|6-Iodoindolin-2-one|95%
Brand: Ambeed
SKU: A203574
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Quality Control of [ 919103-45-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 919103-45-0 ]

CAS No. :	919103-45-0	MDL No. :	MFCD09835633
Formula :	C₈H₆INO	Boiling Point :	365°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	259.04 g/mol	Pubchem ID :	53418819
Synonyms :

Calculated chemistry of of [ 919103-45-0 ]

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 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) :	-6.6 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 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: US2007/15748,2007,A1 .Location in patent: Page/Page column 5

2
[ 99365-40-9 ]
[ 919103-45-0 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: US2007/15748,2007,A1 .Location in patent: Page/Page column 5

3
[ 919103-50-7 ]
[ 919103-45-0 ]
[ 919103-51-8 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: US2007/15748,2007,A1 .Location in patent: Page/Page column 6

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 ]

Reference： [1]Patent: WO2014/9318,2014,A1
[2]Patent: US2014/18372,2014,A1

5
[ 919103-45-0 ]
[ 1537909-08-2 ]

Reference： [1]Patent: WO2014/9318,2014,A1

6
[ 919103-45-0 ]
[ 98-88-4 ]
[ 1535204-23-9 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: WO2014/9318,2014,A1 .Location in patent: Page/Page column 88; 89
[2]Patent: US2014/18372,2014,A1 .Location in patent: Paragraph 0494-0498
[3]Patent: WO2014/9319,2014,A1 .Location in patent: Page/Page column 67
[4]Patent: US2014/18405,2014,A1 .Location in patent: Paragraph 0388-0389

7
[ 919103-45-0 ]
[ 1535204-24-0 ]

Reference： [1]Patent: WO2014/9319,2014,A1
[2]Patent: US2014/18405,2014,A1

8
[ 919103-45-0 ]
[ 1535283-64-7 ]

Reference： [1]Patent: WO2014/9319,2014,A1

9
[ 919103-45-0 ]
[ 1535204-21-7 ]

Reference： [1]Patent: WO2014/9319,2014,A1
[2]Patent: US2014/18405,2014,A1

10
[ 919103-45-0 ]
C₂₄H₂₂IN₃O [ No CAS ]

Reference： [1]Patent: US2014/18372,2014,A1

11
[ 919103-45-0 ]
[ 1535204-25-1 ]

Reference： [1]Patent: US2014/18405,2014,A1

12
[ 41252-95-3 ]
[ 919103-45-0 ]

Reference： [1]Patent: US2014/66634,2014,A1
[2]Patent: US2014/66634,2014,A1
[3]Patent: WO2014/37307,2014,A1

13
[ 1573120-04-3 ]
[ 919103-45-0 ]

Yield	Reaction Conditions	Operation 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 ).

Reference： [1]Patent: US2014/66634,2014,A1 .Location in patent: Paragraph 0030; 0031
[2]Patent: WO2014/37307,2014,A1 .Location in patent: Page/Page column 10; 11

14
[ 1338507-93-9 ]
[ 919103-45-0 ]

Yield	Reaction Conditions	Operation 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 ).

Reference： [1]Patent: US2014/66634,2014,A1 .Location in patent: Paragraph 0032; 0033
[2]Patent: WO2014/37307,2014,A1 .Location in patent: Page/Page column 11; 12

15
[ 88-73-3 ]
[ 919103-45-0 ]

Reference： [1]Patent: US2014/66634,2014,A1
[2]Patent: US2014/66634,2014,A1
[3]Patent: WO2014/37307,2014,A1
[4]Patent: WO2014/37307,2014,A1

16
[ 919103-45-0 ]
[ 2973-77-5 ]
C₁₅H₈Br₂INO₂ [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 8288 - 8294

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 919103-45-0 ]

Quality Control of [ 919103-45-0 ]

Related Doc. of [ 919103-45-0 ]

Product Details of [ 919103-45-0 ]

Calculated chemistry of of [ 919103-45-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 919103-45-0 ]

Application In Synthesis of [ 919103-45-0 ]

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

Related Functional Groups of [ 919103-45-0 ]

Iodides

Amides

Related Parent Nucleus of [ 919103-45-0 ]

Indolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 919103-45-0 ]

Related Parent Nucleus of
[ 919103-45-0 ]