2-Methylindole-3-carboxaldehyde Chemical Properties

Melting point:

200-201 °C (lit.)

Boiling point:

344.3±22.0 °C(Predicted)

Density 

1.226±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

16.08±0.30(Predicted)

form 

Powder

color 

Brown

CAS DataBase Reference

5416-80-8(CAS DataBase Reference)

EPA Substance Registry System

1H-Indole-3-carboxaldehyde, 2-methyl- (5416-80-8)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-Methylindole-3-carboxaldehyde Usage And Synthesis

Chemical Properties

Brown powder

Uses

Reactant for preparation of:• ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1• ;Fluorescent sensors (BODIPY)2• ;Antimicrobial agents against methicillin-resistant Staphylococcus aureus3• ;G protein-coupled receptor CRTh2 antagonists4• ;Inhibitors of PI3 kinase-α5• ;Antitubercular agents6• ;Anti-inflammatory agents7• ;Mycobacterium tuberculosis protein tyrosine phosphatase B8• ;Glucocorticoid receptor ligands9• ;Agents stimulating neurite outgrowth10

Uses

Reactant for preparation of:

• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
• Fluorescent sensors (BODIPY)
• Antimicrobial agents against methicillin-resistant Staphylococcus aureus
• G protein-coupled receptor CRTh2 antagonists
• Inhibitors of PI3 kinase-α
• Antitubercular agents
• Anti-inflammatory agents
• Mycobacterium tuberculosis protein tyrosine phosphatase B
• Glucocorticoid receptor ligands
• Agents stimulating neurite outgrowth

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 31, p. 2892, 1983 DOI: 10.1248/cpb.31.2892

General Description

Oxidative activation of 2-methylindole-3-carboxaldehyde via N-heterocyclic carbene organocatalysis generates heterocyclic ortho-quinodimethane as a key intermediate.

Synthesis

GENERAL PROCEDURE: Phosphorus oxychloride (POCl3, 1.73 mL, 18.6 mmol) was slowly added dropwise to stirred and ice-bath cooled N,N-dimethylformamide (DMF, 5.0 mL). The reaction mixture was stirred at 1-5 °C for 20 min before a solution of 2-methylindole (15.5 mmol) in DMF (5.0 mL) was slowly added. The resulting reaction mixture was gradually warmed to 35 °C and maintained at this temperature for 40 min. The mixture was then cooled to room temperature. Ice (about 10 g) was added to the mixture, followed by the addition of 5 M sodium hydroxide (NaOH) solution (31 mL, 155 mmol). The reaction mixture was heated at 95 °C for 30 min and then cooled to room temperature. Ice (~10 g) was again added to the mixture and the resulting reaction mixture was stirred for 30 minutes. 2-Methylindole-3-carbaldehyde was collected by filtration and washed several times with distilled water.

References

[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 12, p. 2895 - 2901
[2] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1014 - 1018
[3] Chemical Biology and Drug Design, 2011, vol. 78, # 5, p. 864 - 868
[4] European Journal of Medicinal Chemistry, 2003, vol. 38, # 1, p. 75 - 87
[5] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167

2-Methylindole-3-carboxaldehyde(5416-80-8)Related Product Information

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• 1,2,3,9-TETRAHYDRO-4H-9-METHYL-CARBAZOLE-4-ONE
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• 1-Methyl-2-phenylindole-3-carboxaldehyde
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• 1-METHYLINDOLE-3-CARBOXALDEHYDE,1-Methylindole-3-carboxaldehyde, 98+%,1-METHYLINDOLE-3-CARBOXALDEHYDE 98% (HPLC)
• 5-METHOXY-1-METHYLINDOLE-3-CARBOXALDEHYDE