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2-Methylindole

CAS No.95-20-5
Chemical Name:2-Methylindole
CBNumber:CB1711727
Molecular Formula:C9H9N
Formula Weight:131.17
MOL File:95-20-5.mol

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)
EWG's Food Scores 1
FDA UNII I7CN58827I
NIST Chemistry Reference 1H-Indole, 2-methyl-(95-20-5)
EPA Substance Registry System 1H-Indole, 2-methyl- (95-20-5)
UNSPSC Code 12352200
NACRES NA.24

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

NFPA 704:

	1
2		1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302
Precautionary statements P264-P270-P301+P312-P501

2-Methylindole Price More Price(7)

Brand: Sigma-Aldrich(India)
Product number: M51407
Product name : 2-Methylindole
Purity: 98%
Packaging: 25G
Price: ₹1948.5
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: M51407
Product name : 2-Methylindole
Purity: 98%
Packaging: 100G
Price: ₹3593.9
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 41069
Product name : 2-Methylindole
Purity: analytical standard
Packaging: 100MG
Price: ₹6765.63
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: M0346
Product name : 2-Methylindole
Purity: min. 99.0 %
Packaging: 25G
Price: ₹3800
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: M0346
Product name : 2-Methylindole
Purity: min. 99.0 %
Packaging: 100G
Price: ₹9600
Updated: 2022/05/26
Buy: Buy

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.
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
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.
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.]