| Identification | More | [Name]
4-Acetoxyindole | [CAS]
5585-96-6 | [Synonyms]
4-ACETOXYINDOLE
4-INDOLYL ACETATE
4-INDOXYL ACETATE
4-INDOLYL ACETATE 99%
ACETOXYINDOLE
4-Acetoxy-1H-indole
Acetic acid 1H-indol-4-yl ester | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C10H9NO2 | [MDL Number]
MFCD00010678 | [Molecular Weight]
175.18 | [MOL File]
5585-96-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
100-102°C | [Boiling point ]
339.1±15.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
16.38±0.30(Predicted) | [color ]
Off-White to Beige | [InChI]
InChI=1S/C10H9NO2/c1-7(12)13-10-4-2-3-9-8(10)5-6-11-9/h2-6,11H,1H3 | [InChIKey]
ZXDMUHFTJWEDEF-UHFFFAOYSA-N | [SMILES]
N1C2=C(C(OC(=O)C)=CC=C2)C=C1 | [CAS DataBase Reference]
5585-96-6(CAS DataBase Reference) |
| Questions and Answers (Q&A) | Back Directory | [Description]
4-acetoxylindole is also known as 4-Indolyl acetate. It can be used as standards of the reverse phase HPLC during separation of small molecules. It can also be used as reactant during the preparation of inhibitors of HIV-attachment, prostanoid EP3 antagonist, indolyl-nitroalkanes and psilocybin.
| [References]
http://www.sigmaaldrich.com/catalog/product/aldrich/259047?lang=en®ion=US
https://pubchem.ncbi.nlm.nih.gov/compound/4-Acetoxyindole
|
| Hazard Information | Back Directory | [Uses]
Reactant for preparation of:• ;Inhibitors of HIV-1 attachment1• ;Prostanoid EP3 receptor antagonist, as a novel antiplatelet agent2• ;Indolyl-nitroalkanes via N-bromosuccinimide catalyzed synthesis3• ;Psilocybin as a medicinal agent4 | [Application]
In addition to its pharmaceutical applications, 4-Acetoxyindole is also employed in the synthesis of functional materials and organic electronics. Its distinctive properties enable it to be used in the development of dyes and pigments, enhancing the performance of various industrial products. | [General Description]
4-Acetoxyindole is a chromophore that belongs to the pyrrole family of compounds. It has been shown to react with an ionic liquid under acidic conditions to form a protonated intermediate, which can be deprotonated by a nucleophile. This reaction yields an acetate anion and a fluorescing product. 4-Acetoxyindole also reacts with deuterium gas, yielding an acetate, a deuterium atom, and fluorescing product. The reaction is reversible and the yield of the product depends on the concentration of the reactants. 4-Acetoxyindole has strong carbonyl groups that make it reactive towards other functional groups. These reactions are useful for synthesizing heterocycles such as indoles and isoquinolines.
| [Synthesis]
4-Hydroxyindole (1 eq. of limiting reagent) was loaded into the vessel under N2, followed by DCM (dichloromethane; based on the loading of 4-hydroxyindole, 6 v/v). The reaction was cooled to 0-5 °C and pyridine (1.2 eq.) was added dropwise at 0-5 °C. Acet |
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Wuxi Pengruilai Trading Co.,Ltd Gold
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15370273536 18761559979 |
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Energy Chemical
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400-0056266 |
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www.energy-chemical.com |
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China Langchem Inc.
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0086-21-58956006 |
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