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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:
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 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

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
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.
Manas K Ghorai et al.
The Journal of organic chemistry, 78(8), 3867-3878 (2013-04-04)
A practical approach for the synthesis of 3-substituted indolines via regio- and stereoselective SN2-type ring-opening of 2-(2-halophenyl)-N-tosylaziridines with heteroatomic nucleophiles (O, N, and S) followed by palladium-catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and enantiomeric
Tanguy Saget et al.
Organic letters, 15(6), 1354-1357 (2013-03-05)
The synthesis of cyclopropyl spiroindolines is described using an intramolecular palladium(0)-catalyzed C-H functionalization of a methine C(sp(3))-H bond. This transformation can be coupled with intermolecular Suzuki couplings or direct arylations of heteroaromatics to access functionalized indoline scaffolds in a single
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