| Identification | More | [Name]
2-Methylindole | [CAS]
95-20-5 | [Synonyms]
1H-INDOLE, 2-METHYL-
2-METHYL-1H-INDOLE
2-METHYLINDOLE
ALPHA-METHYLINDOLE
AURORA 15496
LABOTEST-BB LT01274391
METHYLINDOLE(2-)
METHYLKETOLE
2-methyl-1h-indol
2-methyl-indol
Indole, 2-methyl-
-Methyl-1H-indole
-Methylindole
2-Methylindole, 98+%
a-Methylindol
2-METHYLINDOLE TECHNICAL GRADE | [EINECS(EC#)]
202-398-3 | [Molecular Formula]
C9H9N | [MDL Number]
MFCD00005616 | [Molecular Weight]
131.17 | [MOL File]
95-20-5.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to reddish-purple or brown crystals, flakes | [Melting point ]
57-59 °C (lit.) | [Boiling point ]
273 °C (lit.) | [density ]
1,07 g/cm3 | [refractive index ]
1.6070 (estimate) | [Fp ]
141 °C
| [storage temp. ]
Freezer (-20°C) | [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Crystals, Flakes, or Crystalline Powder | [pka]
17.57±0.30(Predicted) | [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 | [Detection Methods]
HPLC,NMR | [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]
95-20-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
3335 | [WGK Germany ]
3
| [RTECS ]
NM0345000
| [F ]
8-10-13-23 | [TSCA ]
Yes | [HS Code ]
29339990 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow to reddish-purple or brown crystals, flakes | [Uses]
2-Methylindole is an intermediate in the synthesis of indole derivative with potential antifungal activities. | [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 | [Definition]
ChEBI: A methylindole that is 1H-indole substituted by a methyl group at position 2. | [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.] |
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