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I5605

Sigma-Aldrich

Indoline

ReagentPlus®, 99%

Synonym(s):

1-Azaindan, 2,3-Dihydroindole

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About This Item

Empirical Formula (Hill Notation):
C8H9N
CAS Number:
496-15-1
Molecular Weight:
119.16
Beilstein/REAXYS Number:
111915
EC Number:
207-816-8
MDL number:
MFCD00005705
UNSPSC Code:
12352100
PubChem Substance ID:
24896074
NACRES:
NA.22

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

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

199.4 °F - closed cup

flash_point_c

93 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

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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)
Toshiharu Noji et al.
Organic letters, 15(8), 1946-1949 (2013-04-04)
A benzyne-mediated synthesis of substituted indolines and carbazoles was developed. The reaction includes generation of benzyne using Mg(TMP)2·2LiCl as a base, cyclization, and trapping the resulting organomagnesium intermediate with an electrophile to provide a series of substituted indolines and carbazoles
Gang He et al.
Organic letters, 14(12), 2944-2947 (2012-06-08)
An efficient method has been developed for the synthesis of indoline compounds from picolinamide (PA)-protected β-arylethylamine substrates via palladium-catalyzed intramolecular amination of ortho-C(sp(2))-H bonds. These reactions feature high efficiency, low catalyst loadings, mild operating conditions, and the use of inexpensive
Oktay Talaz et al.
Bioorganic & medicinal chemistry, 21(6), 1477-1482 (2012-11-06)
Several 1,4-bis(indolin-1-ylmethyl)benzene-based compounds containing substituents such as five, six and seven cyclic derivatives on indeno part (9a-c) were prepared and tested against two members of the pH regulatory enzyme family, carbonic anhydrase (CA). The inhibitory potencies of the compounds at
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
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