| Identification | More | [Name]
2-Methylindole-3-carboxaldehyde | [CAS]
5416-80-8 | [Synonyms]
2-METHYL-1H-INDOLE-3-CARBALDEHYDE
2-METHYL-3-FORMYLINDOLE
2-METHYLINDOLE-3-CARBALDEHYDE
2-METHYLINDOLE-3-CARBOXALDEHYDE
2-METHYLINDOLE-3-CARBOXYALDEHYDE
3-FORMYL-2-METHYLINDOLE
AKOS 233-93
AKOS BBS-00000868
AKOS JY2083591
AURORA KA-4266
OTAVA-BB BB0127441736
2-methyl-1h-indole-3-carboxaldehyd
2-Methyindole-3-Carboxaldehyde
2-Methyl Indole-3-Carboxaldehyd
1H-Indole-3-carboxaldehyde, 2-methyl-(9CI)
2-Methyl-3-indolecarboxaldehyde
2-Methylindole-3-formaldehyde
2-Methylindole-3-carboxaldehyde, 97+%
2-Methyl-3-formyl-1H-indole
3-Formyl-2-methyl-1H-indole | [EINECS(EC#)]
226-512-6 | [Molecular Formula]
C10H9NO | [MDL Number]
MFCD00012077 | [Molecular Weight]
159.18 | [MOL File]
5416-80-8.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Brown powder | [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
| [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 | [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 |
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