[ CAS No. 59-48-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Structure of 59-48-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 59-48-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 59-48-3 ]

SDS Specification

Alternatived Products of [ 59-48-3 ]

Product Details of [ 59-48-3 ]

CAS No. :	59-48-3	MDL No. :	MFCD00005711
Formula :	C₈H₇NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JYGFTBXVXVMTGB-UHFFFAOYSA-N
M.W :	133.15	Pubchem ID :	321710
Synonyms :	2-Indolinone;NSC 274863;Indolin-2-one;2-Oxindole;2-indolone	Chemical Name :	Indolin-2-one

Calculated chemistry of [ 59-48-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
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 :	41.73
TPSA :	29.1 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.42
Log Po/w (XLOGP3) :	1.16
Log Po/w (WLOGP) :	0.61
Log Po/w (MLOGP) :	1.13
Log Po/w (SILICOS-IT) :	1.91
Consensus Log Po/w :	1.25

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	1.92 mg/ml ; 0.0144 mol/l
Class :	Very soluble
Log S (Ali) :	-1.37
Solubility :	5.73 mg/ml ; 0.043 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.85
Solubility :	0.186 mg/ml ; 0.0014 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.18

Safety of [ 59-48-3 ]

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 [ 59-48-3 ]

* 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 [ 59-48-3 ]
Downstream synthetic route of [ 59-48-3 ]

[ 59-48-3 ] Synthesis Path-Upstream 1~5

1
[ 59-48-3 ]
[ 459-57-4 ]
[ 3476-86-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With piperidine In ethanol at 90℃; Inert atmosphere	General procedure: The appropriate aldehyde (1 equiv) was added to EtOH (3 mL/0.2 mmol) and the mixture was stirred until complete solution. Theoxindole (1 equiv) and piperidine (0.1 equiv) were added, and themixture was heated to 90°C for 3-7 h, and cooled. The resultingprecipitatewas filtered, washed with cold ethanol and dried to givethe pure compound. If necessary, additional recrystallization inethanol was applied to obtain the pure product.

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 286 - 307
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 5, p. 2077 - 2090
[3] Journal of Chemical Research, 2018, vol. 42, # 5, p. 244 - 246

2
[ 59-48-3 ]
[ 459-57-4 ]
[ 3476-86-6 ]
[ 90828-17-4 ]

Yield	Reaction Conditions	Operation in experiment
25%	With piperidine In ethanol for 3 h; Reflux	General procedure: The preparation of compounds 3-25 was carried out by refluxing oxindole with different aromatic aldehydes in ethanol in the presence of a catalytic amount of piperidine were refluxed for 3 h. After cooling reaction mixture was concentrated at reduced pressure to obtain solid of 3-oxindole derivatives, then washed with 1:1 mixture of hexane-ethyl acetate (25 mL) and dried to afford titles compoundsin good yields (Table 1). Only in two cases (10 and21), both E and Z isomers were obtained, these isomers wereseparated by column chromatography using 1:9 ethyl acetate: hexane as eluent. The structures of synthetic compounds 3-25 were elucidated by 1H NMR and EI MS. Elemental analysis results were also found to be satisfactory.

Reference： [1] Medicinal Chemistry, 2013, vol. 9, # 5, p. 681 - 688

3
[ 59-48-3 ]
[ 142273-20-9 ]

Reference： [1] European Journal of Organic Chemistry, 2012, # 5, p. 1019 - 1024

4
[ 59-48-3 ]
[ 6287-38-3 ]
[ 114727-43-4 ]

Reference： [1] Heterocyclic Communications, 2008, vol. 14, # 4, p. 263 - 267
[2] European Journal of Medicinal Chemistry, 1992, vol. 27, # 8, p. 779 - 789

5
[ 59-48-3 ]
[ 252882-61-4 ]

Reference： [1] Patent: US6172076, 2001, B2,
[2] Patent: WO2008/144266, 2008, A1,
[3] Patent: US2008/306102, 2008, A1,

[ 59-48-3 ] Synthesis Path-Downstream 1~11

1
[ 59-48-3 ]
[ 92-55-7 ]
[ 2731-46-6 ]

Reference： [1]Patent: US2872372,1957,

2
[ 59-48-3 ]
[ 20876-36-2 ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 563 - 567
[2]Zhurnal Obshchei Khimii,1956,vol. 26,p. 2019,2023, 2024; engl. Ausg. S. 2251, 2254, 2255
[3]MedChemComm,2014,vol. 5,p. 655 - 658
[4]Archiv der Pharmazie,2015,vol. 348,p. 715 - 729

3
[ 110-89-4 ]
[ 59-48-3 ]
[ 54439-75-7 ]
3-[2-Chloro-4-methoxybenzylidenyl]-2-indolinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
680.2 mg (62%)	In ethanol;	3-[2-Chloro-4-methoxybenzylidenyl]-2-indolinone (SU5480). The reaction mixture of 487.9 mg (3.7 mmoles) of oxindole, 750 mg (4.3 mmoles) of <strong>[54439-75-7]2-<strong>[54439-75-7]chloro-4-methoxybenzaldehyde</strong></strong> and 4 drops of piperidine in 5 mL of ethanol was heated to 90° C. for 2 h and cooled to room temperature. The yellow precipitate was filtered, washed with cold ethanol, and dried at 40° C. in a vacuum oven overnight to give 680.2 mg (62percent) of the title compound.
680.2 mg (62%)	In ethanol;	3-[2-Chloro-4-methoxybenzylidenyl]-2-indolinone (SU5480). The reaction mixture of 487.9 mg (3.7 mmoles) of oxindole, 750 mg (4.3 mmoles) of <strong>[54439-75-7]2-<strong>[54439-75-7]chloro-4-methoxybenzaldehyde</strong></strong> and 4 drops of piperidine in 5 mL of ethanol was heated to 90° C. for 2 h and cooled to room temperature. The yellow precipitate was filtered, washed with cold ethanol, and dried at 40° C. in a vacuum oven overnight to give 680.2 mg (62percent) of the title compound.

Reference： [1]Patent: US5883113,1999,A
[2]Patent: US5834504,1998,A

4
[ 59-48-3 ]
[ 34595-26-1 ]
C₂₀H₂₀N₂O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 1632 - 1636

5
[ 15307-79-6 ]
[ 59-48-3 ]
[ 87-65-0 ]
[ 15362-40-0 ]
[ 69220-40-2 ]
[ 601-88-7 ]
[ 15307-93-4 ]
[ 10113-35-6 ]
[ 6697-95-6 ]
[ 39920-37-1 ]
[ 13603-93-5 ]
[ 608-31-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; iron(II); In water; at 20℃;pH 2.0;	General procedure: For the Fenton degradation experiment, 10 mL of a Milli Q water sample acidified at pH 2 with 100 muL H2SO4 0.5 mol/L containing 200 ng of each studied anti-inflammatory drug (diclofenac sodium, ibuprofen and ketoprofen) was placed into a 50 mL brown glass bottle. Immediately, 500 muL of Fe2+solution (1 mg/mL Fe2+) and 200 muL of H2O2 (30percent) were added into the brown bottle which was kept under magnetic stirring and room temperature for different time intervals in order to perform the degradation process. Because the catalyst (Fe2+) and the oxidant (H2O2) are consumed very fast, these were refreshed at each 30 minutes in the same amounts as it was described previously. To study the Fenton oxidative process efficiency over the selected drugs, different experiments at 30, 60 and 120 minutes were performed. After each Fenton oxidative experiment, the degradation by-products of NAIDs were extracted with organic solvent and analyzed by GC×GC-qMS.

Reference： [1]Revue Roumaine de Chimie,2014,vol. 59,p. 1021 - 1027

6
[ 59-48-3 ]
[ 186534-02-1 ]
colletotrichumine A [ No CAS ]

Reference： [1]Heterocyclic Communications,2015,vol. 21,p. 335 - 336

7
[ 59-48-3 ]
[ 3032-81-3 ]
[ 321981-86-6 ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 203 - 207

8
[ 10268-06-1 ]
[ 59-48-3 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4864 - 4867

9
[ 59-48-3 ]
[ 391-12-8 ]
C₁₇H₉F₃N₂O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 10099 - 10103

10
[ 59-48-3 ]
[ 34595-26-1 ]
2',3',4',4a'-tetrahydro-1'H,6'H-spiro[indoline-3,5'-pyrido[1,2-a]quinolin]-2-one [ No CAS ]
2',3',4',4a'-tetrahydro-1'H,6'H-spiro[indoline-3,5'-pyrido[1,2-a]quinolin]-2-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7109 - 7114

11
[ 59-48-3 ]
[ 145549-76-4 ]
(aR)-tert-butyl 3-(2-oxoindolin-3-ylidene)cyclobutane-1-carboxylate [ No CAS ]
tert-butyl 3-(2-oxoindolin-3-ylidene)cyclobutane-1-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 3013 - 3017

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Isomers

Technical Information

? Acyl Group Substitution ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 59-48-3 ]

Amides

[ 3484-35-3 ]

5-Methylindolin-2-one

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[ 56341-38-9 ]

6-Methyl-2-indolinone

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[ 20876-36-2 ]

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6-Aminoindolin-2-one

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5-Aminoindolin-2-one hydrochloride

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Related Parent Nucleus of
[ 59-48-3 ]

Indolines

[ 3484-35-3 ]

5-Methylindolin-2-one

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[ 56341-38-9 ]

6-Methyl-2-indolinone

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P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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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:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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P420	Store away from other materials.
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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.
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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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
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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H301	Toxic if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 59-48-3 ] {[proInfo.proName]}

Quality Control of [ 59-48-3 ]

Related Doc. of [ 59-48-3 ]

Product Details of [ 59-48-3 ]

Calculated chemistry of [ 59-48-3 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 59-48-3 ]

Application In Synthesis of [ 59-48-3 ]

[ 59-48-3 ] Synthesis Path-Upstream 1~5

[ 59-48-3 ] Synthesis Path-Downstream 1~11

Technical Information

Related Functional Groups of [ 59-48-3 ]

Amides

Related Parent Nucleus of [ 59-48-3 ]

Indolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 59-48-3 ]

Related Parent Nucleus of
[ 59-48-3 ]