4-Acetoxyindole

Base Information

• Chemical Name: 4-Acetoxyindole
• CAS No.: 5585-96-6
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 2933990090
• Mol file: 5585-96-6.mol

Synonyms:1H-Indol-4-ol,acetate (ester) (9CI);Indol-4-ol, acetate (7CI);Indol-4-ol, acetate (ester)(8CI);4-Indolylacetate;

Chemical Property of 4-Acetoxyindole

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 9.41E-05mmHg at 25°C
• Melting Point: 100-102 °C
• Refractive Index: 1.633
• Boiling Point: 339.1 °C at 760 mmHg
• PKA: 16.38±0.30(Predicted)
• Flash Point: 158.9 °C
• PSA: 42.09000
• Density: 1.255 g/cm³
• LogP: 2.09320
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

4-Acetoxyindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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.
• Uses: Reactant for preparation of:Inhibitors of HIV-1 attachmentProstanoid EP3 receptor antagonist, as a novel antiplatelet agentIndolyl-nitroalkanes via N-bromosuccinimide catalyzed synthesisPsilocybin as a medicinal agent 4-Acetoxyindole is a useful intermediate for organic synthesis of Psilocine and Psilocine analogs. 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

Technology Process of 4-Acetoxyindole

There total 5 articles about 4-Acetoxyindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

1H-indol-4-ol (2380-94-1) + acetic anhydride (108-24-7) → acetic acid 1H-indol-4-yl ester (5585-96-6)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 25 ℃; Inert atmosphere; Large scale;

Reference yield: 69.0%

trans-6-benzyloxy-2-nitro-β-pyrrolindino -styrene + 3-nitro-o-cresol (5460-31-1) → acetic acid 1H-indol-4-yl ester (5585-96-6)

Guidance literature:

With 2-(Dimethylamino)pyridine; acetic anhydride; triethylamine; palladium-carbon; In ethyl acetate;

Reference yield:

→ acetic acid 1H-indol-4-yl ester (5585-96-6)

Guidance literature:

With ethanol; iron; acetic acid;

upstream raw materials:

ethanol

acetic acid

1H-indol-4-ol

acetic anhydride

Downstream raw materials:

3-(2-nitro-1-phenylethyl)-1H-indol-4-yl acetate

4-acetoxy-3-(N,N-diisopropylaminoethyl)indole

[3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate

3-(2-(dibenzylamino)ethyl)-1H-indol-4-ol

Refernces

• 1、 Singh, Jasbir,Zeller, Wayne,Zhou, Nian,Hategan, Georgeta,Mishra, Rama K.,Polozov, Alex,Yu, Peng,Onua, Emmanuel,Zhang, Jun,Ramírez, José L.,Sigthorsson, Gudmundur,Thorsteinnsdottir, Margret,Kiselyov, Alex S.,Zembower, David E.,Andrésson, Thorkell,Gurney, Mark E.. "Structure - activity relationship studies leading to the identification of (2E)-3-[l-[(2,4-dichlorophenyl)methyl]-5-fluoro-3-methyl-lH-indol-7-yl]-N-[(4, 5-dichloro-2-thienyl)sulfonyl]-2-propenamide (DG-041), a potent and selective prostanoid EP3 receptor antagonist, as a novel antiplatelet agent that does not prolong bleeding". experimental part. p. 18 - 36. Retrieved 2010/04/26.
• 2、 -. "Process for the preparation of 5,6-diacetoxyindole". . . Retrieved 2008/06/13.