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ChemicalBook--->CAS DataBase List--->5585-96-6

5585-96-6

5585-96-6 Structure

5585-96-6 Structure
IdentificationMore
[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 PropertiesBack 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)
Safety DataBack Directory
[Hazard Codes ]

Xi
[WGK Germany ]

3
[Hazard Note ]

Irritant
[HS Code ]

2933998090
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&region=US
https://pubchem.ncbi.nlm.nih.gov/compound/4-Acetoxyindole
Hazard InformationBack 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
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

4-Acetoxyindole(5585-96-6)MS
4-Acetoxyindole(5585-96-6)1HNMR
4-Acetoxyindole(5585-96-6)13CNMR
4-Acetoxyindole(5585-96-6)IR1
4-Acetoxyindole(5585-96-6)IR2
4-Acetoxyindole(5585-96-6)Raman
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

5585-96-6(sigmaaldrich)
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