27640-31-9

Basic information

• Product Name: 2,3-DIHYDRO-1H-INDOL-2-YLMETHANOL
• Synonyms: 2,3-DIHYDRO-1H-INDOL-2-YLMETHANOL;2-HYDROXYMETHYL-2,3DIHYDRO-(1H)-INDOLE;2-(Hydroxymethyl)indoline;2,3-Dihydro-2-(hydroxymethyl)-1H-indole, (2,3-Dihydro-1H-indol-2-yl)methanol;indolin-2-ylmethanol
• CAS NO: 27640-31-9
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• Mol File: 27640-31-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 48-57
• Boiling Point: 309.1°Cat760mmHg
• Flash Point: 166°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 0.000282mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 2,3-DIHYDRO-1H-INDOL-2-YLMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-1H-INDOL-2-YLMETHANOL(27640-31-9)
• EPA Substance Registry System: 2,3-DIHYDRO-1H-INDOL-2-YLMETHANOL(27640-31-9)

Safety Data

• Hazard Codes: C,Xn
• Statements: 22
• Hazardous Substances Data: 27640-31-9(Hazardous Substances Data)

Usage

General Description

2,3-Dihydro-1H-indol-2-ylmethanol, also known as indolin-2-ylmethanol, is a chemical compound with the molecular formula C9H11NO. It is a white solid at room temperature and is soluble in polar solvents such as water and methanol. 2,3-DIHYDRO-1H-INDOL-2-YLMETHANOL is often used as a building block in the synthesis of pharmaceuticals and other organic compounds. It has been studied for its potential therapeutic properties and is also used as a reagent in chemical reactions. The compound is of interest to researchers and chemists for its diverse applications in the field of organic chemistry.

InChI:InChI=1/C9H11NO/c11-6-8-5-7-3-1-2-4-9(7)10-8/h1-4,8,10-11H,5-6H2

Upstream product

• 16851-56-2 indolin-2-yl carboxylic acid 
• 39597-68-7 (2,3-dihydro-indol-1-yl)-acetic acid methyl ester 
• 172647-94-8 methyl 7-azaindol-1-acetate 
• 172648-34-9 ethyl 1-methyl-7-azaindole-2-carboxylate 
• 33140-80-6 methyl indol-1-ylacetate 
• 76182-48-4 methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 59040-84-5 indoline-2-carboxylic acid methyl ester 
• 62-53-3 aniline 
• 589-09-3 N-allyl-N-phenylamine 
• 32704-22-6 2-allyl-phenylamine 
• 111457-18-2 N-(2-allyl-phenyl)-benzamide 
• 24621-70-3 2-(hydroxymethyl)indole 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 

Downstream Products

• 321744-15-4 (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,3-dihydro-1H-indole 
• 135829-04-8 benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate 
• 150535-14-1 2-<(methoxycarbonyl)methyl>indoline 

Relevant articles and documents

Design and synthesis of novel indoline-(thio)urea hybrids

A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst

The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.

Kinetic resolutions of lndolines by a nonenzymatic acylation catalyst

The first method for the kinetic resolution of indolines through catalytic N-acylation is described. To improve the selectivity factor, new planar-chiral PPY-derived catalysts were synthesized, wherein the chiral environment was systematically modified. This work provides a rare example of a nonenzyme-based acylation catalyst for the kinetic resolution of amines. Copyright