5-Methoxyindole

CAS NO.：1006-94-6
Empirical Formula: C9H9NO
Molecular Weight: 147.17
MDL number: MFCD00005674
EINECS: 213-745-3
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-21 22:41:43

What is 5-Methoxyindole?

Chemical properties

white to light brownish crystalline powder

The Uses of 5-Methoxyindole

5-Methoxyindole (cas# 1006-94-6) is a compound useful in organic synthesis. It can be used to synthesis 1-(Phenylsulfonyl)-5-methoxy-1H-indole.

What are the applications of Application

5-Methoxyindole is a simple methoxy indole compound

Preparation

The synthesis of 5-methoxyindole from 5-methoxy-2-oxindole: Conversion of 5-methoxy-2-oxindole to 5-methoxyindole was accomplishedby the chlorination of 5-methoxy-2-oxindole with triphenylphosphine-carbontetrachloride in acetonitrile followed by the catalytic reduction of a chlorine atom in 66% total yield.

Definition

ChEBI: 5-methoxyindole is a member of indoles.

Reactions

5-methoxyindole was treated with sodium hydroxide and phenylsulfonyl chloride in the presence of a catalytic amount of tetrabutylammonium bromide to afford 1-(phenylsulfonyl)indole and 5-methoxy-1-(phenylsufonyl)indole in excellent yields of 100%.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 1405, 1989 DOI: 10.1002/jhet.5570260533
The Journal of Organic Chemistry, 58, p. 5558, 1993 DOI: 10.1021/jo00072a052
Tetrahedron Letters, 27, p. 837, 1986 DOI: 10.1016/S0040-4039(00)84114-3

Purification Methods

Crystallise 5-methoxyindole from cyclohexane pet ether or pet ether/Et2O. [Saito & Kikugawa J Heterocycl Chem 16 1325 1979, Beilstein 21 III/IV 765, 21/3 V 18.]

Properties of 5-Methoxyindole

Melting point:	52-55 °C (lit.)
Boiling point:	176-178 °C/17 mmHg (lit.)
Density	1.1135 (rough estimate)
refractive index	1.5310 (estimate)
Flash point:	176-178°C/17mm
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Chloroform, Methanol
pka	16.70±0.30(Predicted)
form	Crystalline Powder
color	White to light brownish
Water Solubility	insoluble
Sensitive	Light Sensitive
BRN	116722
CAS DataBase Reference	1006-94-6(CAS DataBase Reference)
NIST Chemistry Reference	1H-Indole, 5-methoxy-(1006-94-6)

Safety information for 5-Methoxyindole

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.