Indoline Property

Melting point:

-21 °C

Boiling point:

220-221 °C (lit.)

Density 

1.063 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.592(lit.)

Flash point:

199 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

5g/l; lnsoluble in water, soluble in alcohol and oils. Poorly soluble in Propylene glycol.

pka

5.20±0.20(Predicted)

form 

liquid (clear)

color 

clear dark brown

Odor

a mild, delicate, but extremely tenacious floral odor

Water Solubility 

5 g/L (20 ºC)

Sensitive 

Light Sensitive

BRN 

111915

CAS DataBase Reference

496-15-1(CAS DataBase Reference)

NIST Chemistry Reference

1H-Indole, 2,3-dihydro-(496-15-1)

EPA Substance Registry System

1H-Indole, 2,3-dihydro- (496-15-1)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-37/39-26

WGK Germany 

3

RTECS 

NL6906300

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29339990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

Indoline Chemical Properties,Usage,Production

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.

Uses

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

Uses

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.

Uses

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

Indolene is manufactured from (theoretically) 2 Mol. Indole plus 1 Mol. Hydroxycitronellal by condensation under heating. The proportions may vary slightly, and it is common practice to add Diethyl phthalate to the mixture prior to heating, so that the condensation product is somewhat protected against local overheating, and the finished product becomes light of color and fairly pourable at room temperature.