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2-Methylindole

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2-Methylindole Basic information

Product Name:
2-Methylindole
Synonyms:
  • ALPHA-METHYLINDOLE
  • 2-Methylindole, 98+%
  • a-Methylindol
  • 2-METHYLINDOLE TECHNICAL GRADE
  • 2-Methylindole 99.0%
  • 2-Methylindole, 98% 100GR
  • 2-METHYLINDOLE FOR SYNTHESIS 100 G
  • NSC 7514
CAS:
95-20-5
MF:
C9H9N
MW:
131.17
EINECS:
202-398-3
Product Categories:
  • Heterocycle-Indole series
  • fine chemical
  • Building Blocks
  • Heterocyclic Building Blocks
  • intermediates
  • fine chemicals
  • Intermediates of Dyes and Pigments
  • Indoles and derivatives
  • Indole
  • Indoles
  • Simple Indoles
  • bc0001
Mol File:
95-20-5.mol
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2-Methylindole Chemical Properties

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)
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Safety Information

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
8-10-13-23
TSCA 
Yes
HS Code 
29339990

MSDS

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2-Methylindole Usage And Synthesis

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.]

2-Methylindole Preparation Products And Raw materials

Raw materials

Preparation Products

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