Indoline

Base Information

• Chemical Name: Indoline
• CAS No.: 496-15-1
• Molecular Formula: C8H9N
• Molecular Weight: 119.166
• Hs Code.: 2933.99
• European Community (EC) Number: 207-816-8
• UNII: 6DPT9AB2NK
• DSSTox Substance ID: DTXSID9052133
• Nikkaji Number: J40.156K
• Wikipedia: Indoline
• Wikidata: Q2613101
• Metabolomics Workbench ID: 52338
• ChEMBL ID: CHEMBL388803
• Mol file: 496-15-1.mol

Synonyms:2,3-dihydro-1H-indole;indoline

Chemical Property of Indoline

Chemical Property:

• Appearance/Colour: Clear colorless to slightly brown liquid
• Vapor Pressure: 0.0783mmHg at 25°C
• Melting Point: -21 °C
• Refractive Index: n20/D 1.592(lit.)
• Boiling Point: 227.2 °Cat 760 mmHg
• PKA: 5.20±0.20(Predicted)
• Flash Point: 92.8 °C
• PSA: 12.03000
• Density: 1.04 g/cm³
• LogP: 1.79260
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: 5g/l
• Water Solubility.: 5 g/L (20 ºC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 119.073499291
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Indoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: C1CNC2=CC=CC=C21
• Uses: As an indole derivative, Indoline can be used in the preparation of various medicinal compounds such as potential α1-adrenoceptor (α1-AR) antagonists. Indole is used in perfumery and in preparing tryptophan, one of the 20 amino acids commonly found in animal proteins. It has important application in the industry of plant growth. It is used to prepare indoleacetic acid (auxin) and other plant growth substances which help the development of roots in plant. Indole and its derivatives are widely used in making perfumes, dyes, agrochemicals and medicines. Reactant for preparation of:Inhibitors of NOD1-Induced Nuclear Factor-κB ActivationSphingosine-1-phosphate 4(S1P4) receptor antagonistsCytotoxic cell cycle inhibitors2-AminopyridinesPET agent for imaging of protein kinase C (PKC)Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetesα4β2-Nicotinic acetylcholine receptor-selective partial agonistsmGlu4 positive allosteric modulatorsBacterial biofilm inhibitorsSerotonin 5-HT6 receptor antagonists

Technology Process of Indoline

There total 135 articles about Indoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-(benzyloxycarbonyl)indoline (132431-12-0) → 1-indoline (496-15-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; ethylenediamine; In tetrahydrofuran; at 20 ℃; for 1.5h; under 760 Torr;

DOI:10.1016/S0040-4020(00)00771-7

Reference yield: 99.0%

indole (120-72-9) → 1-indoline (496-15-1)

Guidance literature:

With hydrogen; In water; at 100 ℃; for 10h; under 22502.3 Torr;

DOI:10.1016/j.apcata.2019.117183

Reference yield: 97.0%

1-Acetyl-2,3-dihydro-1H-indole (16078-30-1) → 1-indoline (496-15-1) + 1-ethylindoline (5876-09-5)

Guidance literature:

With triethyl borane; Triethoxysilane; sodium hydroxide; In hexane; at 80 ℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube;

upstream raw materials:

indole

2-oxoindole

(2-bromoethyl)-2-nitrobenzene

2-aminophenethyl alcohol

Downstream raw materials:

5-(2,3-dihydro-indol-1-yl)-3-phenyl-thiazolidine-2,4-dione

4-(2,3-dihydro-indol-5-ylmethylene)-2-phenyl-4H-oxazol-5-one

1-[1β-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanoyl]-2,3-dihydro-indole

1-benzyl-2,3-dihydro-1H-indole

Refernces

• 1、 Scott Wiens,Johnson, Jerry L.,Gribble, Gordon W.. "Concerning the preparation of 6-bromotryptamine". . . Retrieved 2021/03/15.
• 2、 Timelthaler, Daniel,Topf, Christoph. "Heterogeneous Hydrogenation of Quinoline Derivatives Effected by a Granular Cobalt Catalyst". . . Retrieved 2021/11/22.