| Identification | More | [Name]
5-(Phenylmethoxy)-1H-indole-3-carbaldehyde | [CAS]
6953-22-6 | [Synonyms]
5-(BENZYLOXY)-1H-INDOLE-3-CARBALDEHYDE
5-BENZYLOXY-3-FORMYLINDOLE
5-(BENZYLOXY)-3-INDOLECARBOXYALDEHYDE
5-BENZYLOXYINDOLE-3-ALDEHYDE
5-BENZYLOXYINDOLE-3-CARBALDEHYDE
5-BENZYLOXYINDOLE-3-CARBOXALDEHYDE
5-BENZYLOXY INDOLE-3-CARBOXYALDEHYDE
5-BENZYLOXYINDOLE-3-FORMALDEHYDE
5-(phenylmethoxy)-1h-indole-3-carbaldehyde
5-BENZYLOXY-3-INDOLECARBOXALDEHYDE
5-(Phenylmethoxy)-1H-indole-3-carboxaldehyde
NSC 71049
5-Benzyloxy-3-formaldehyde
5-(Benzyloxy)-1H-indole-3-carboxaldehyde
5-Benzyloxy-3-formyl-1H-indole
5-Benzyloxyindole-3-carboxaldehyde ,98% | [EINECS(EC#)]
230-134-7 | [Molecular Formula]
C16H13NO2 | [MDL Number]
MFCD00014562 | [Molecular Weight]
251.28 | [MOL File]
6953-22-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
237-238°C | [Boiling point ]
474.2±30.0 °C(Predicted) | [density ]
1.267±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Ethanol | [form ]
powder
| [pka]
15.13±0.30(Predicted) | [color ]
yellow to brown
| [Sensitive ]
Air Sensitive | [Usage]
An antibacterial agent | [Detection Methods]
HPLC,NMR | [BRN ]
208873 | [InChI]
1S/C16H13NO2/c18-10-13-9-17-16-7-6-14(8-15(13)16)19-11-12-4-2-1-3-5-12/h1-10,17H,11H2 | [InChIKey]
DJGNUBADRQIDNQ-UHFFFAOYSA-N | [SMILES]
O=Cc1c[nH]c2ccc(OCc3ccccc3)cc12 | [CAS DataBase Reference]
6953-22-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36:Irritating to the eyes.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37:Wear suitable protective clothing and gloves .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT, AIR SENSITIVE | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Sens. 1 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
Reactant for preparation of:
- Rhodanine merocyanine dyes
- Potential topoisomerase II inhibitors
- Azithromycin derivatives
- Inhibitors of PI3 kinase-α and the mammalian target of rapamycin
- Cytotoxic agents
- Vascular endothelial growth factor (VEGF) inhibitor
- Derivatives of vancomycin and eremomycin
- Benzimidazoles as potential antibacterial agents
- Light-dependent tumor necrosis factor-α antagonists
- Serotonin 5-HT4 Receptor agonists
| [Uses]
An antibacterial agent | [Synthesis]
a) Synthesis of 5-(benzyloxy)-1H-indole-3-carbaldehyde: Phosphoryl chloride (1.5 g, 9.9 mmol) was slowly added dropwise to 15 mL of N,N-dimethylformamide (DMF) cooled in an ice bath under stirring conditions. After removing the ice bath, the reaction was continued with stirring for 15 min. Subsequently, 5-benzyloxyindole (2.00 g, 8.96 mmol) was added and the reaction mixture was heated to 50-60 °C and maintained at this temperature for 1.5 hours. After completion of the reaction, the mixture was poured into ice water and adjusted to alkaline with 2 M sodium hydroxide solution. The mixture was refluxed for 2 minutes, cooled and filtered to collect the solid product. The solid was washed with water and dried to give the target compound 5-(benzyloxy)-1H-indole-3-carboxaldehyde in a yield of 1.88 g (84% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6) with the following chemical shifts: δ 5.88 (s, 1H), 8.20 (s, 1H), 7.68 (d, 1H), 7.50-7.25 (m, 6H), 6.96 (dd, 1H), 5.11 (s, 2H), 4.02 (s, 1H). | [References]
[1] Patent: WO2005/66132, 2005, A1. Location in patent: Page/Page column 90-91
[2] Patent: US2007/299061, 2007, A1. Location in patent: Page/Page column 17
[3] Synthesis (Germany), 2017, vol. 49, # 18, p. 4141 - 4150
[4] Journal of the Chemical Society, 1958, p. 3493,3494
[5] Journal of the Chemical Society, 1958, p. 3887,3892 |
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