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59-48-3 Indolin-2-one

59-48-3 Indolin-2-one

Oxindole Basic information Oxindole Chemical Properties Safety Information Oxindole Usage And Synthesis Oxindole Preparation Products And Raw materials Upstream information 2-(trimethylsilanyl)ethanesulfonic acid phenylamide; 3-hydroxyindolin-2-one; methanol; Sulfuric acid;...

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Product Details:

Oxindole Basic information

Product Name:

Oxindole

Synonyms:

OXINDOL;OXINDOLE;O-(AMINOPHENYL)ACETIC ACID LACTAM;TIMTEC-BB SBB004215;1,3-dihydro-2h-indol-2-on;1,3-Dihydro-indol-2-one;1,3-Dihydroindol-2-one;2,3-dihydroindol-2-one

CAS:

59-48-3

MF:

C8H7NO

MW:

133.15

EINECS:

200-429-5

Product Categories:

blocks;IndolesOxindoles;Aromatic Phenylacetic Acids and   Derivatives;Indoles   and derivatives;Indoline   & Oxindole;Indoles;Indole Derivatives;Heterocycle-Indole series

Mol File:

59-48-3.mol

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Oxindole Chemical Properties

Appearance:

off-white crystalline powder

Melting   Point:

123-128ºC

Boiling   Point:

227ºC (73 mmHg)

Flash   Point:

161.4ºC

Refractive   Index:

1.586

Water   Solubility:

insoluble

Stability:

Stable under normal temperatures and pressures.

Storage   Condition:

Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Boiling point

227 °C (73 mm Hg)

Fp

194-196°C/17mm

solubility

9.1g/l

BRN

114692

CAS DataBase Reference

59-48-3(CAS DataBase Reference)

NIST Chemistry Reference

2H-Indol-2-one, 1,3-dihydro-(59-48-3)

EPA Substance Registry System

2H-Indol-2-one, 1,3-dihydro-(59-48-3)


Safety Information

Hazard Codes

Xn

Risk Statements

22

Safety Statements

22-24/25

RIDADR

2811

WGK Germany

3

RTECS

NM2080500

HazardClass

6.1(b)

PackingGroup

III

HS Code

29337900


Oxindole Usage And Synthesis

Chemical Properties

beige to yellowish-orange or pinkish-brown powder

Uses

Indole analogue; shows pharmacological activity

Definition

ChEBI: An indolinone carrying an oxo group at position 2.Oxindole (2-indolone) is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. Oxindole is a modified indoline with a substituted carbonyl at the second position of the 5-member indoline ring.

Oxindole is a tryptophan derivative and in human biology is formed by gut bacteria ("normal flora"). It is normally metabolized and detoxified from the body by the liver. In excess, it can cause sedation, muscle weakness, hypotension, and coma. Patients with hepatic encephalopathy have been recorded to have elevated serum oxindole levels.

Intermediate as

252916-29-3 TSU-68 (SU6668,   Orantinib), 194413-58-6 Semaxanib (SU5416)


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Synthesis route

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Reference:

El Kazzouli, Said; Koubachi, Jamal; Berteina-Raboin, Sabine; Mouaddib, Abderrahim; Guillaumet, Gerald Tetrahedron Letters, 2006 , vol. 47, # 48 p. 8575 - 8577


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Reference:

Naik, Nilesh H.; Urmode, Tukaram D.; Sikder,   Arun K.; Kusurkar, Radhika S. Australian Journal of Chemistry, 2013 , vol.   66, # 9 p. 1112 - 1114


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Reference:

1. Applied Catalysis A: General, vol. 470, p. 427 - 433

2. Lichtenecker, Roman J.; Schmid, Walther Monatshefte fur Chemie, 2009 , vol. 140, # 5 p. 509 - 512

3. Journal of Molecular Catalysis B: Enzymatic, vol. 67, #1-2 p. 29-35


Oxindole Preparation Products And Raw materials

Preparation Products

5-Bromo-2-oxindole


Upstream information

2-(trimethylsilanyl)ethanesulfonic acid phenylamide; 3-hydroxyindolin-2-one; methanol; Sulfuric acid; 4-nitro-1,2-phenylenediamine; acetylacetone; pyridine-3-carbaldehyde; quinoline; 1-iodo-4-methoxybenzene; Ammonia;


Downtream information

3,3-Dipropinylindolin-2-on; 5-(2-bromopropanoyl)-1,3-dihydroindol-2-one; 3-(anilinomethylidene)-1H-indol-2-one; 5-acetyl-1,3-dihydroindol-2-one; 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydroindol-2-one; 3-hydroxyindolin-2-one; methanol; diclofenac; Oxalic acid; Ammonia


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