2-methylindole

Structural formula
General
Surname	2-methylindole
other names	alpha-methylindole
Molecular formula	C 9 H 9 N
Brief description	white to gray-brown solid with an unpleasant odor
External identifiers / databases
CAS number 95-20-5 EC number 202-398-3 ECHA InfoCard 100.002.181 PubChem 7224 Wikidata Q4596907
properties
Molar mass	131.18 g mol −1
Physical state	firmly
density	1.07 g cm −3
Melting point	58-60 ° C
boiling point	272 ° C
solubility	poorly soluble in water
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 318 P: 280-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-methylindole is an aromatic heterocycle from the group of nitrogen heterocycles and a derivative of indole .

Extraction and presentation

2-methylindole can be obtained by reacting o -methylacetanilide with sodium amide in ether at 240 ° C. and subsequent reaction with ethanol and water. It can also be obtained from coal tar .

properties

2-methylindole is a flammable, hardly inflammable, light-sensitive, white to gray-brown solid with an unpleasant odor, which is sparingly soluble in water. It is isomeric to skatole (3-methylindole) and shows triboluminescence .

use

2-Methylindole is used as a reagent for the regioselective synthesis of oxopyrrolidine analogues via iodine-catalyzed Markovnikov addition reactions , Friedel-Crafts alkylations , the production of plant growth inhibitors , Michael additions and the synthesis of cyclooxygenase-1 / cyclooxygenase-2 inhibitors. It is also used in the production of azo dyes and fragrances .

Individual evidence

1. ↑ ^{a b c d} Entry on 2-methylindole. In: Römpp Online . Georg Thieme Verlag, accessed on June 25, 2016.
2. ↑ ^{a b c d e f g h i} Entry on 2-methylindole in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
3. ↑ CFH Allen, James VanAllan: 2-METHYLINDOLE In: Organic Syntheses . 22, 1942, p. 94, doi : 10.15227 / orgsyn.022.0094 ; Coll. Vol. 3, 1955, p. 597 ( PDF ).
4. ↑ Data sheet 2-methylindole, 98% from Sigma-Aldrich , accessed on June 25, 2016 ( PDF ).