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I5605

Sigma-Aldrich

Indoline

ReagentPlus®, 99%

Synonym(s):
2,3-Dihydroindole, 1-Azaindan
Empirical Formula (Hill Notation):
C8H9N
CAS Number:
Molecular Weight:
119.16
Beilstein:
111915
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

assay

99%

form

liquid

refractive index

n20/D 1.592 (lit.)

bp

220-221 °C (lit.)

density

1.063 g/mL at 25 °C (lit.)

SMILES string

C1Cc2ccccc2N1

InChI

1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2

InChI key

LPAGFVYQRIESJQ-UHFFFAOYSA-N

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Application

Reactant for preparation of:
  • Inhibitors of NOD1-Induced Nuclear Factor-κB Activation
  • Sphingosine-1-phosphate 4(S1P4) receptor antagonists
  • Cytotoxic cell cycle inhibitors
  • 2-Aminopyridines
  • PET agent for imaging of protein kinase C (PKC)
  • Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes
  • α4β2-Nicotinic acetylcholine receptor-selective partial agonists
  • mGlu4 positive allosteric modulators
  • Bacterial biofilm inhibitors
  • Serotonin 5-HT6 receptor antagonists

Packaging

25, 100 g in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

199.4 °F - closed cup

Flash Point(C)

93 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Matej Baláž et al.
Molecules (Basel, Switzerland), 24(18) (2019-09-22)
Performing solution-phase oximation reactions with hydroxylamine hydrochloride (NH2OH·HCl) carries significant risk, especially in aqueous solutions. In the present study, four N-substituted indole-3-carboxaldehyde oximes were prepared from the corresponding aldehydes by solvent-free reaction with NH2OH·HCl and a base (NaOH or Na2CO3)
Ke Chen et al.
Organic & biomolecular chemistry, 10(32), 6600-6606 (2012-07-17)
A palladacycle-catalyzed tandem Heck-intramolecular aza-Michael reaction protocol has been developed for the one-pot synthesis of 1-substituted isoindolines from N-unprotected 2-bromobenzylamines and acrylates with high yields.
A diversity-oriented approach to spiroindolines: post-Ugi gold-catalyzed diastereoselective domino cyclization.
Sachin G Modha et al.
Angewandte Chemie (International ed. in English), 51(38), 9572-9575 (2012-08-22)
François Brucelle et al.
Organic letters, 14(12), 3048-3051 (2012-06-01)
A simple approach to prepare indolines and benzopyrrolizidinones from ortho-azidoallylbenzenes via a tandem radical addition/cyclization is described. The use of triethylborane to initiate and sustain the process provides the best results. Indolines are easily converted into the corresponding indoles by
Jan Michael Schuller et al.
Journal of molecular biology, 422(1), 87-99 (2012-06-12)
Fungal indole prenyltransferases (PTs) typically act on specific substrates, and they are able to prenylate their target compounds with remarkably high regio- and stereoselectivity. Similar to several indole PTs characterized to date, the cyclic dipeptide N-prenyltransferase (CdpNPT) is able to

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