Indoline

Chemical properties

2,3-Dihydroindole [496-15-1], indoline C8H9N, Mr 119.16, bp 229 – 230 ℃(101.3 kPa), is a colorless liquid, which is volatile in steam and soluble in diethyl ether, acetone, and benzene, but only slightly soluble in water. Indoline is obtained by hydrogenation of indole or by catalytic cyclodehydration of 2-(2-aminophenyl)ethanol. A range of pharmaceuticals, as well as fungicides and bactericides, can be produced from indoline.

The Uses of Indoline

As an indole derivative, Indoline can be used in the preparation of various medicinal compounds such as potential α1-adrenoceptor (α1-AR) antagonists.

The Uses of Indoline

Indoline 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.

The Uses of Indoline

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

Definition

ChEBI: Indoline is a member of indoles.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 7812, 1974 DOI: 10.1021/ja00832a035
Synthetic Communications, 13, p. 489, 1983 DOI: 10.1080/00397918308081827

Synthesis

Indoline can be produced from the reaction of indole,zinc and 85% phosphoric acid.