57240
Indoline
purum, ≥98.0% (GC)
Synonym(s):
1-Azaindan, 2,3-Dihydroindole
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About This Item
Empirical Formula (Hill Notation):
C8H9N
CAS Number:
Molecular Weight:
119.16
EC Number:
207-816-8
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
111915
MDL number:
grade
purum
assay
≥98.0% (GC)
form
liquid
color
clear dark brown
refractive index
n20/D 1.592
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
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
Regulatory Information
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Kamalkishor P Landge et al.
The Journal of organic chemistry, 77(13), 5705-5713 (2012-06-08)
An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indoline compounds
María López-Iglesias et al.
The Journal of organic chemistry, 77(18), 8049-8055 (2012-08-25)
Racemic indolines including a variety of structural motifs such as C-2 and C-3 substitutions (alkyl or aryl), cis/trans relative stereochemistry and functionalization of the aromatic ring (fluoro, methyl or methoxy groups) have been efficiently prepared through Fischer indolization and subsequent
Zhaoyang Liu et al.
Molecules (Basel, Switzerland), 18(3), 3107-3117 (2013-03-09)
A donor-acceptor (D-A) type indoline dye, D149, was used as an electron donor in solution-processed organic solar cells (OSCs). For bulk-heterojunction (BHJ) type OSCs with PC70BM as electron acceptor, the power conversion efficiency (PCE) is sensitive to the amount of
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
Lu Wang et al.
Organic letters, 14(15), 3978-3981 (2012-07-27)
3-Acylindoles undergo nucleophilic-type reactions with Grignard reagents to efficiently afford either cis- or trans-substituted indolines, depending on the different quenching procedures. The enolate intermediate could be trapped by aryl acyl chlorides to provide indolines bearing a quaternary carbon center with
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