251550-17-1

Basic information

• Product Name: 3-Isobutyl-2-oxindole
• Synonyms: 3-ISOBUTYL-1,3-DIHYDRO-INDOL-2-ONE;3-Isobutyl-2-oxindole;3-isobutyl-1,3-dihydro-2H-indol-2-one;3-Isobutyl-1,3-dihydro-1H-indol-2-one;3-Isobutylindolin-2-one, 1,3-Dihydro-3-(2-methylprop-1-yl)-2H-indol-2-one;3-(2-methylpropyl)-2,3-dihydro-1H-indol-2-one
• CAS NO: 251550-17-1
• Molecular Formula: C₁₂H₁₅NO
• Molecular Weight: 189.25
• Mol File: 251550-17-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 96.0-97.0 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• Boiling Point: 313.6 °C at 760 mmHg
• Flash Point: 185 °C
• Appearance: /
• Density: 1.039 g/cm³
• Vapor Pressure: 0.00049mmHg at 25°C
• Refractive Index: 1.525
• PKA: 14.81±0.40(Predicted)
• CAS DataBase Reference: 3-Isobutyl-2-oxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isobutyl-2-oxindole(251550-17-1)
• EPA Substance Registry System: 3-Isobutyl-2-oxindole(251550-17-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 251550-17-1(Hazardous Substances Data)

Usage

General Description

3-Isobutyl-2-oxindole is an organic synthetic compound belonging to the class of indoles, which are aromatic heterocyclic compounds. This chemical is white in appearance and crystalline in state. It has the molecular formula C10H13NO with a molar mass of 163.22 g·mol?1. The compound is widely used in various areas of organic synthesis and drug discovery, offering pivotal intermediate for the synthesis of several biologically active compounds. As it has a chiral center, it can exist in different stereoisomeric forms. Because of their varied bioactive profiles and widespread existence in natural products, indoles like 3-Isobutyl-2-oxindole have always been of great interest in chemical and pharmaceutical research.

InChI:InChI=1/C12H15NO/c1-8(2)7-10-9-5-3-4-6-11(9)13-12(10)14/h3-6,8,10H,7H2,1-2H3,(H,13,14)

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 91-56-5 indole-2,3-dione 
• 443-69-6 5-fluoro-1H-indole-2,3-dione 
• 59-48-3 2-oxoindole 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 1353717-79-9 (S)-3-(hydroxy(phenyl)amino)-3-isobutylindolin-2-one 
• 1376933-31-1 (R)-3-isobutyl-3-(phenylthio)indolin-2-one 

Relevant articles and documents

Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindoles

Quinidine derivative (QD)2PYR was found to catalyze the asymmetric direct amination of unprotected prochiral 3-oxindole with DIAD to construct quaternary stereocenters at the C3 position with excellent enantioselectivity.

A Facile Method for the Synthesis of 3-Alkyloxindole

Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.

(Phenylpiperazinyl-butyl)oxindoles as selective 5-HT7 receptor antagonists

A series of potent 5-hydroxytryptamine7 (5-HT7) ligands has been synthesized that contain a 1,3-dihydro2H-indol-2-one (oxindole) skeleton. The binding of these compounds to the 5-HT7 and 5-HT 1A receptors was measured. Despite the structural similarity of these two serotonin receptor subtypes, several derivatives exhibited a high selectivity to the 5-HT7 receptor. According to the structure-activity relationship observations, compounds unsubstituted at the oxindole nitrogen atom and containing a tetramethylene spacer between the oxindole skeleton and the basic nitrogen atom are the most potent ligands. Concerning the basic group, besides the moieties of the 4-phenylpiperazine type, halophenyl-1,2,3,6-tetrahydropyridines also proved to be 5-HT7 receptor-ligands. Because of halogen substitution on the aromatic rings, good metabolic stability could be achieved. A representative of the family, 3-{4-[4-(4-chlorophenyl)-piperazin-1-yl]-butyl}-3-ethyl-6-fluoro-1, 3-dihydro-2H-indol-2-one (9e′) exhibited selective 5-HT7 antagonist activity (K: = 0.79 nM). The in vivo pharmacological potencies of these 5-HT7 receptor-ligands were estimated by the conflict drinking (Vogel) and the light-dark anxiolytic tests.