2-Methylindole
- Product Name
- 2-Methylindole
- CAS No.
- 95-20-5
- Chemical Name
- 2-Methylindole
- Synonyms
- 2-METHYL-1H-INDOLE;1H-INDOLE, 2-METHYL-;NSC 7514;AURORA 15496;METHYLKETOLE;a-Methylindol;-Methylindole;2-methyl-indol;2-METHYLINDOLE;METHYLINDOLE(2-)
- 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)
- 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..…
N-Bromosuccinimide Price
- Product number
- M51407
- Product name
- 2-Methylindole
- Purity
- 98%
- Packaging
- 25g
- Price
- $50.7
- Updated
- 2024/03/01
- Product number
- 41069
- Product name
- 2-Methylindole
- Purity
- analytical standard
- Packaging
- 100mg
- Price
- $182
- Updated
- 2022/05/15
- Product number
- M0346
- Product name
- 2-Methylindole
- Purity
- >99.0%(GC)
- Packaging
- 25g
- Price
- $47
- Updated
- 2024/03/01
- Product number
- M0346
- Product name
- 2-Methylindole
- Purity
- min. 99.0 %
- Packaging
- 100G
- Price
- $119
- Updated
- 2024/03/01
- Product number
- A10764
- Product name
- 2-Methylindole, 98+%
- Packaging
- 50g
- Price
- $45.65
- Updated
- 2024/03/01
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.]
2-Methylindole Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2-Methylindole manufacturers
- Product
- 2-Methylindole 95-20-5
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20 ton
- Release date
- 2024-12-12
- Product
- 2-Methylindole 95-20-5
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 30tons/month
- Release date
- 2023-02-24
- Product
- 2-Methylindole 95-20-5
- Price
- US $0.00-0.00/KG
- Min. Order
- 5mg
- Purity
- 99%HPLC
- Supply Ability
- 2000tons
- Release date
- 2020-01-06