27640-33-1

Basic information

• Product Name: (S)-(+)-2-INDOLINEMETHANOL
• Synonyms: (S)-(+)-Indoline-2-methanol, 98+%;(S)-(+)-2-IndolineMethanol, 98+%;(S)-(+)-2-Indolinemethanol 97%;(S)-indolin-2-ylmethanol;(S)-(+)-INDOLINE-2-METHANOL;(S)-(+)-2-INDOLINEMETHANOL;(S)-2,3-DIHYDRO-1H-INDOL-2-YLMETHANOL;[(2S)-2,3-dihydro-1H-indol-2-yl]methanol
• CAS NO: 27640-33-1
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 27640-33-1.mol
• Article Data: 30

Chemical Properties

• Melting Point: 64.5-69.5 °C(lit.)
• Boiling Point: 309.1°C at 760 mmHg
• Flash Point: 166°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 0.000282mmHg at 25°C
• Refractive Index: 1.565
• PKA: 14.42±0.10(Predicted)
• CAS DataBase Reference: (S)-(+)-2-INDOLINEMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-INDOLINEMETHANOL(27640-33-1)
• EPA Substance Registry System: (S)-(+)-2-INDOLINEMETHANOL(27640-33-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 27640-33-1(Hazardous Substances Data)

Usage

General Description

(S)-(+)-2-Indolinemethanol is a chemical compound that belongs to the class of indole alkaloids. It is a chiral molecule, meaning that it has a non-superimposable mirror image, and the (S)-(+)-enantiomer is the biologically active form. (S)-(+)-2-INDOLINEMETHANOL is commonly used in the synthesis of pharmaceuticals and other organic compounds due to its versatile reactivity and potential medicinal properties. (S)-(+)-2-Indolinemethanol has been studied for its potential as a therapeutic agent in cancer treatment and has also shown promise as a chiral auxiliary in the synthesis of complex molecules in organic chemistry. Its unique chemical properties and potential biological activity make it a valuable compound in various scientific and industrial applications.

InChI:InChI=1/C9H11NO/c11-6-8-5-7-3-1-2-4-9(7)10-8/h1-4,8,10-11H,5-6H2/t8-/m0/s1

Upstream product

• 59040-84-5 indoline-2-carboxylic acid methyl ester 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 76182-48-4 methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate 
• 33140-80-6 methyl indol-1-ylacetate 
• 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 
• 50501-07-0 (S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester 
• 24621-70-3 2-(hydroxymethyl)indole 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 111457-18-2 N-(2-allyl-phenyl)-benzamide 
• 32704-22-6 2-allyl-phenylamine 
• 589-09-3 N-allyl-N-phenylamine 

Downstream Products

• 313234-76-3 1-[(2S)-2-(hydroxymethyl)indolinyl]-2-{4-[(4-chlorophenyl)methyl]piperazinyl}ethan-1-one 
• 502634-02-8 (S)-(-)-N-benzyl-2-(hydroxymethyl)-5-nitroindoline 
• 502634-03-9 (S)-(+)-N-benzyl-2-[[[N-(tert-butoxycarbonyl)-L-valyl]oxy]methyl]-5-nitroindoline 
• 197460-26-7 (S)-tert-butyl 2-((tosyloxy)methyl)indoline-1-carboxylate 
• 180479-44-1 ((R)-2,2-Dimethyl-1-phenyl-propyl)-((S)-2-methoxymethyl-2,3-dihydro-indol-1-yl)-amine 
• 150535-14-1 2-<(methoxycarbonyl)methyl>indoline 
• 135829-04-8 benzyl 2-(Hydroxymethyl)-1-indolinecarboxylate 
• 1031238-94-4 (3aS)-1-(4-nitrophenoxy)-3a,4-dihydro-3H-[1,3,2]oxazaphospholo[3,4-a]indole 1-oxide 
• 1031238-96-6 C₁₅H₁₃BrNO₃P 
• 1031238-92-2 C₁₅H₁₄NO₃P 
• 1031238-93-3 C₁₅H₁₃ClNO₃P 
• 1094359-58-6 (S)-(1-tosylindolin-2-yl)methanol 
• 1186240-95-8 (S)-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanol 
• 1226884-79-2 (S)-1-(4-(2-(hydroxymethyl)indolin-1-yl)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone 

Relevant articles and documents

SYNTHESIS OF PYRROLIZIDINES AND RELATED COMPOUNDS BY ALDOL CYCLIZATION OF N--α-AMINOALDEHYDES

Treatment of 1--2-pyrrolidinecarbaldehyde with sodium hydride in tetrahydrofuran (THF) gave the aldol condensation product, 5,6,7,7a-tetrahydro-2-methylthio-3H-pyrrolizin-3-one.However, when the same aldehyde was treated with sodium hydroxide in aqueous THF, 5,6,7,7a-tetrahydro-7a-hydroxy-3-methylthio-3H-pyrrolizin-3-one was obtained.These reactions were applied to the synthesis of indolizidine and pyrroloindole derivatives.

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.

Enantioselective Synthesis of 2-Bromomethyl Indolines via BINAP(S)-Catalyzed Bromoaminocyclization of Allyl Aniline

An enantioselective bromoamination of allyl aniline with N-bromosuccinimide (NBS) catalyzed by BINAP(S) (BINAP monosulfide) is described. This protocol could provide a range of chiral 2-bromomethyl indolines in good to excellent yields with up to 87% ee.