ChemicalBook > CAS DataBase List > Indoline

Indoline

Product Name
Indoline
CAS No.
496-15-1
Chemical Name
Indoline
Synonyms
Dihydroindole;2,3-DIHYDRO-1H-INDOLE;2,3-DIHYDROINDOLE;1H-Indole, 2,3-dihydro-;IDN;NDOLINE;INDOLINE;1-Azaindan;1H-Indoline;Indoline>
CBNumber
CB5485525
Molecular Formula
C8H9N
Formula Weight
119.16
MOL File
496-15-1.mol
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
I5605
Product name
Indoline
Purity
ReagentPlus , 99%
Packaging
25g
Price
$40.09
Updated
2025/07/31
Sigma-Aldrich
Product number
I5605
Product name
Indoline
Purity
ReagentPlus , 99%
Packaging
100g
Price
$86.1
Updated
2025/07/31
TCI Chemical
Product number
I0033
Product name
Indoline
Purity
>98.0%(GC)(T)
Packaging
25mL
Price
$34
Updated
2025/07/31
TCI Chemical
Product number
I0033
Product name
Indoline
Purity
>98.0%(GC)(T)
Packaging
250mL
Price
$191
Updated
2025/07/31
TRC
Product number
I627200
Product name
Indoline
Packaging
5g
Price
$45
Updated
2021/12/16
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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.

Application

In organic chemistry, indoline derivatives are widely used as chiral auxiliary groups or chiral ligands, playing a crucial role in asymmetric synthesis. For example, (S)-Indoline-2-methanol is an important starting material for the synthesis of many chiral compounds. Through asymmetric catalytic reactions, such as the asymmetric rearrangement reaction of iridium porphyrin-catalyzed indoles with aryl diazonium esters, chiral 2-indoline tertiary alcohols can be synthesized efficiently.

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.

Indoline Preparation Products And Raw materials

Raw materials

Preparation Products

2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACID 5-CYANO-2,3-DIHYDRO-1H-INDOLE 1-ACETYL-5-AMINO-2,3-DIHYDRO-(1H)-INDOLE 1-Acetyl-5-bromoindoline 5-AMINOINDOLE HYDROCHLORIDE INDOLINE-7-CARBOXYLIC ACID 5-BROMOINDOLINE 6-bromoindoline 6-Nitroindole 1-ACETYL-5-NITROINDOLINE 6-Aminoindole Indole 4-Bromoindoline 7-bromoindoline
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Indoline Suppliers

Americas 1 Austria 1 Belgium 3 Canada 1 China 352 Europe 5 France 1 Germany 10 India 23 Italy 1 Japan 11 Slovakia 1 South Korea 1 Switzerland 2 The Netherlands 2 Ukraine 2 United Kingdom 23 United States 54 Global 494
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View Lastest Price from Indoline manufacturers

Shandong Vital Biotechnology Co., Ltd.
Product
Indoline 496-15-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
100tons
Release date
2025-11-20
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Indoline 496-15-1
Price
US $1.00/KG
Min. Order
1KG
Purity
99.0%-100.00%
Supply Ability
200kg/month
Release date
2021-06-01
Hebei Chuanghai Biotechnology Co., Ltd
Product
Indoline 496-15-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100 mt
Release date
2024-11-28

496-15-1, IndolineRelated Search:

Indometacin cis-Octahydro-isoindole Dihydromyrcenol Indoline-2-carboxylic acid Indole-3-butyric acid Indole-3-acetic acid 2-Methylindoline Indole INDOXYL ACETATE AIDS124803 METHYL 2-INDOLINECARBOXYLATE Indoline-3-carboxylic acid 2,3-DIHYDRO-1H-INDOLE-6-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE Indazole Indobufen Indocyanine green Indole-3-carbinol INDOLAROME

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