| Identification | More | [Name]
Ethyl 3-indoleacetate | [CAS]
778-82-5 | [Synonyms]
1h-indole-3-acetic acid ethyl ester
3-INDOLYL-ACETIC ACID-ETHYL ESTER
ETHYL 3-INDOLACETATE
ETHYL 3-INDOLEACETATE
ethyl indol-3-ylacetate
ETHYL INDOLE-3-ACETATE
IAA ETHYL ESTER
INDOLE-3-ACETIC ACID ETHYL ESTER
Ethyl 1H-indol-3-ylacetate
Ethyl 3-indolylacetate
Ethyl beta-indolylacetate
Ethylindole-3-acetate,98+%
3-INDOLEACETICACIDETHYLESTER
IAA-OEt
(1H-Indole-3-yl)acetic acid ethyl
1H-Indole-3-acetic acid ethyl | [EINECS(EC#)]
212-296-0 | [Molecular Formula]
C12H13NO2 | [MDL Number]
MFCD00005635 | [Molecular Weight]
203.24 | [MOL File]
778-82-5.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R21/22:Harmful in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, 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
| [RTECS ]
NL3528000
| [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
white crystalline powder | [Uses]
Reactant for preparation of:
- Pesticides
- Anti-inflammatory agents
- Antibacterial and antifungal agents
- Anticonvulsant agents
- Hypotensive agents
- Analgesic agents
| [Uses]
Ethyl Indole-3-acetate is a compound used in the synthesis of 9H-Pyrrolo[1,2-α]Indoles via Michael Addition-Condensation with α,β-Unsaturated Ketimines. | [Uses]
Reactant for preparation of:• ;Pesticides1• ;Anti-inflammatory agents2• ;Antibacterial and antifungal agents• ;Anticonvulsant agents • ;Hypotensive agents3• ;Analgesic agents4 | [Definition]
ChEBI: Ethyl 3-indoleacetate is a member of indole-3-acetic acids. | [Synthesis]
Indol-3-ylacetic acid (1.00 g, 5.71 mmol) was dissolved in 25 mL of ethanol and concentrated sulfuric acid (1.0 mL, 18.4 mmol) was added. The reaction mixture was stirred under reflux conditions for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C in an ice bath and subsequently neutralized with 2 N sodium hydroxide solution. The organic solvent was removed by evaporation under reduced pressure and the residue was partitioned between dichloromethane and water. The aqueous phase was extracted twice with dichloromethane, and the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 1.02 g (5.02 mmol, 88% yield) of ethyl indole-3-acetate as a brown oil. The product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 300 MHz, CDCl3): δ 8.09 (br.s, 1H), 7.63 (d, J = 7.69 Hz, 1H), 7.35 (d, J = 7.69 Hz, 1H), 7.04-7.25 (m, 3H), 4.17 (q, J = 7.14 Hz, 2H), 3.77 (s, 2H), 1.26 (t, J = 7.14 Hz, 3H). Ultra performance liquid chromatography-mass spectrometry (UPLC/MS) analysis showed a retention time of 1.58 min, and low resolution mass spectrometry (LRMS) measured m/z 204 ([M+1]+). | [References]
[1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1777 - 1779
[2] Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 10, p. 814 - 824
[3] Patent: EP2548863, 2013, A1. Location in patent: Paragraph 0247
[4] Patent: WO2013/10881, 2013, A1. Location in patent: Page/Page column 95-96
[5] Chinese Chemical Letters, 2013, vol. 24, # 2, p. 127 - 130 |
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