ChemicalBook > CAS DataBase List > 2-Methylindole

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
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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)
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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
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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..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M51407
Product name
2-Methylindole
Purity
98%
Packaging
25g
Price
$50.7
Updated
2024/03/01
Sigma-Aldrich
Product number
41069
Product name
2-Methylindole
Purity
analytical standard
Packaging
100mg
Price
$182
Updated
2022/05/15
TCI Chemical
Product number
M0346
Product name
2-Methylindole
Purity
>99.0%(GC)
Packaging
25g
Price
$47
Updated
2024/03/01
TCI Chemical
Product number
M0346
Product name
2-Methylindole
Purity
min. 99.0 %
Packaging
100G
Price
$119
Updated
2024/03/01
Alfa Aesar
Product number
A10764
Product name
2-Methylindole, 98+%
Packaging
50g
Price
$45.65
Updated
2024/03/01
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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

2-Acetamidotoluene Diethyl ether Sodium amide

Preparation Products

Acemetacin BASIC ORANGE 21 DL-Tryptophan 2-Methylindoline
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2-Methylindole Suppliers

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View Lastest Price from 2-Methylindole manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
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
Shaanxi Dideu Medichem Co. Ltd
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
Hebei Chuanghai Biotechnology Co,.LTD
Product
2-Methylindole 95-20-5
Price
US $9.00/KG
Min. Order
1KG
Purity
99.9
Supply Ability
1 ton
Release date
2024-08-20

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