2-Methylindole Property

Melting point:

57-59 °C (lit.)

Boiling point:

273 °C (lit.)

Density 

1,07 g/cm³

refractive index 

1.6070 (estimate)

Flash point:

141 °C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

17.57±0.30(Predicted)

form 

Crystals, Flakes, or Crystalline Powder

color 

Yellow to reddish-purple or brown

Odor

at 0.10 % in dipropylene glycol. animal indole fresher than skatole with no fecal odor

Odor Type

animal

Water Solubility 

Insoluble in water.

Sensitive 

Light Sensitive

BRN 

109781

InChIKey

BHNHHSOHWZKFOX-UHFFFAOYSA-N

LogP

2.530

CAS DataBase Reference

95-20-5(CAS DataBase Reference)

NIST Chemistry Reference

1H-Indole, 2-methyl-(95-20-5)

EPA Substance Registry System

1H-Indole, 2-methyl- (95-20-5)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-41

Safety Statements 

36/37-24/25-39-26

RIDADR 

3335

WGK Germany 

3

RTECS 

NM0345000

F 

8-10-13-23

TSCA 

Yes

HS Code 

29339990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

2-Methylindole Chemical Properties,Usage,Production

Chemical Properties

Colorless needle or yellow to reddish-purple or brown crystals, flakes. Has an animal type odor.Soluble in ethanol and ether, insoluble in water.

Uses

2-Methylindole is an intermediate in the synthesis of indole derivative with potential antifungal activities. It can be used as a raw material for the preparation of deacetylase (HDAC) inhibitor panobinostat.

Uses

2-Methylindole is used as a reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction, Friedel-Crafts alkylation reactions, preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators, Michael addition reactions and in synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors.

Preparation

2-Methylindole was synthesized from 2-Acetamidotoluene by the following procedure. 2-Acetamidotoluene was added to the mixture of anhydrous ether and sodium amide, heated to 240-260°C under the protection of nitrogen flow, kept for 10min, a large amount of gas was generated in the reaction, and the reaction ended when the gas stopped escaping, and cooled. Ethanol and warm water were added and heated to decompose the sodium derivative of 2-Methylindole and excess sodium amide. After cooling, it was extracted with ether. The extract was concentrated and then distilled, and the fractions at 119-126°C (0.4-0.53kPa) were collected to obtain 2-Methylindole with a yield of 80%-83%. The product can be purified by methanol recrystallization.

Definition

ChEBI: 2-Methylindole is a methylindole that is 1H-indole substituted by a methyl group at position 2. It derives from a hydride of a 1H-indole.

Application

2-Methylindole is used as a reactant Reactant for:
Regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction
Friedel-Crafts alkylation reactions
Preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
Preparation of plant-growth inhibitors
Michael addition reactions
Synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors

Synthesis Reference(s)

Journal of the American Chemical Society, 98, p. 2674, 1976 DOI: 10.1021/ja00425a051
Organic Syntheses, Coll. Vol. 3, p. 597, 1955
Tetrahedron Letters, 9, p. 3499, 1968

Purification Methods

Crystallise it from *benzene. It has also been purified by zone melting. The picrate has m 139o (from Et2O or Et2O/MeOH). [Cohen et al. J Am Chem Soc 82 2184 1960, Beilstein 20 III/IV 3202, 20/7 V 59.]