| Identification | More | [Name]
7-METHYLINDOLE-3-CARBOXALDEHYDE | [CAS]
4771-50-0 | [Synonyms]
3-FORMYL-7-METHYLINDOLE
7-METHYL-1H-INDOLE-3-CARBALDEHYDE
7-METHYLINDOLE-3-ALDEHYDE
7-METHYLINDOLE-3-CARBOXALDEHYDE
7-METHYLINDOLE-3-CARBOXYALDEHYDE
1H-Indole-3-carboxaldehyde, 7-methyl-(9CI)
7-Methylindole-3-carboxaldehyde 98%
7-Methyl-3-indolecarboxaldehyde
7-METHYLINDOLE-3-CARBOXALDEHYDE 98% (HPLC) | [EINECS(EC#)]
-0 | [Molecular Formula]
C10H9NO | [MDL Number]
MFCD00047170 | [Molecular Weight]
159.18 | [MOL File]
4771-50-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
206-208°C | [Boiling point ]
341.0±22.0 °C(Predicted) | [density ]
1.226±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [form ]
Solid | [pka]
15.80±0.30(Predicted) | [color ]
Yellow to brown | [Sensitive ]
Air Sensitive | [BRN ]
122340 | [InChI]
InChI=1S/C10H9NO/c1-7-3-2-4-9-8(6-12)5-11-10(7)9/h2-6,11H,1H3 | [InChIKey]
KTUFZHVVJBHGKZ-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC=C2C)C(C=O)=C1 | [CAS DataBase Reference]
4771-50-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Uses]
Reactant for preparation of:
- Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
- Antibacterial and antituberculosis agents
- Antiandrogens effective against androgen receptor mutants
- Anti-bovine viral diarrhea virus (BVDV) agents
- Receptor subtype 5 antagonists
- Glucocorticoid receptor ligands
- Necroptosis inhibitors
- Orally efficacious small-molecule sctivator of the insulin receptor
| [Uses]
Reactant for preparation of:• ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1• ;Antibacterial and antituberculosis agents2• ;Antiandrogens effective against androgen receptor mutants3• ;Anti-bovine viral diarrhea virus (BVDV) agents4• ;Receptor subtype 5 antagonists5• ;Glucocorticoid receptor ligands6• ;Necroptosis inhibitors7• ;Orally efficacious small-molecule sctivator of the insulin receptor8 | [Synthesis]
General procedure for the synthesis of 7-methylindole-3-carboxaldehyde from 7-methylindole and ouvertropine: To a 50 mL round-bottomed flask fitted with a magnetic stirrer were added sequentially 7-methylindole (1.0 mmol, 1.0 eq.), hexamethylenetetetramine (HMTA, 2.0 mmol, 0.2803 g, 2.0 eq.), activated carbon (0.1 g), and N,N- dimethylformamide (DMF, 2 mL). Iodine (I2, 0.2 mmol, 0.0507 g, 20 mol%) was then added and the flask was assembled with a reflux condenser tube. The reaction mixture was stirred at 120 °C and the progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature. The resulting mixture was filtered through a diatomaceous earth pad and the filter cake was washed well with ethyl acetate (EtOAc, 4 x 6 mL). The combined filtrates were washed sequentially with 0.5 M aqueous hydrochloric acid (10 mL), saturated sodium bicarbonate (NaHCO3) solution (10 mL), and saturated sodium chloride (NaCl) solution (10 mL), dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel fast column chromatography, and the target product 7-methylindole-3-carbaldehyde was obtained by using a mixed solvent of hexane and ethyl acetate as eluent. | [References]
[1] Tetrahedron Letters, 2017, vol. 58, # 30, p. 2877 - 2880
[2] Patent: CN108329249, 2018, A. Location in patent: Paragraph 0041-0044; 0066-0069 |
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