3-Acetoxyindole

Base Information

• Chemical Name: 3-Acetoxyindole
• CAS No.: 608-08-2
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 2933 99 80
• European Community (EC) Number: 210-154-2
• NSC Number: 13964
• UNII: 3AF7Z8794Q
• DSSTox Substance ID: DTXSID6060559
• Nikkaji Number: J16.834C
• Wikidata: Q72483105
• ChEMBL ID: CHEMBL2074590
• Mol file: 608-08-2.mol

Synonyms:indoxyl acetate

Chemical Property of 3-Acetoxyindole

Chemical Property:

• Appearance/Colour: Dark blue solid
• Vapor Pressure: 9.41E-05mmHg at 25°C
• Melting Point: 128-130 °C(lit.)
• Refractive Index: 1.633
• Boiling Point: 339.1 °C at 760 mmHg
• PKA: 15.89±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.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in ethanol, water, chloroform, dichloromethane and methanol.
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

98%, ^*data from raw suppliers

3-Acetoxyindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: CC(=O)OC1=CNC2=CC=CC=C21
• Uses: Useful for detection of esterases3-Indoxyl acetate acts as a colorimetric substrate used for differentiating esterases from various microbiological species. Further, it is used as a plant growth-stimulating hormone and reagent. In addition to this, it acts as a useful synthetic intermediate. INDOXYL ACETATE is a useful synthetic intermediate.

Technology Process of 3-Acetoxyindole

There total 12 articles about 3-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: 76.0%

indole (120-72-9) + [bis(acetoxy)iodo]benzene (3240-34-4) → 3-indoxyl acetate (608-08-2)

Guidance literature:

With potassium hydroxide; In acetonitrile; at 35 ℃; for 1.5h;

DOI:10.1055/s-0030-1258240

Reference yield: 74.0%

5-acetoxy-3-methoxycarbonyl-5H-1,2-benzodiazepine → 3-indoxyl acetate (608-08-2) + ethyl cyanoformate (623-49-4)

Guidance literature:

In dichloromethane; for 0.133333h; Irradiation;

DOI:10.1248/cpb.28.1842

Reference yield: 43.0%

indole (120-72-9) + thallium(III) acetate (2570-63-0) → 3-indoxyl acetate (608-08-2)

Guidance literature:

With acetic acid; at 30 ℃; for 2h;

upstream raw materials:

3-Iodo-1H-indole

silver(I) acetate

2-Acetyl-1H-indol-3-yl-acetat

phenylglycine-o-carboxylic acid

Downstream raw materials:

indole-2,3-dione

1H,1H'-2,2'-Biindolylidene-3,3'-dione

indirubin

N,O-diacetylindoxyl

Refernces

• 1、 Liu, Kexin,Wen, Ping,Liu, Jin,Huang, Guosheng. "A novel and efficient method for the synthesis of 1 H -indol-3-yl acetates". experimental part. p. 3623 - 3626. Retrieved 2010/12/20.
• 2、 Banerji, Avijit,Ray, Rita,Pal, Sudhir C.,Banerji, Debasis,Maiti, Kaustabh K.. "Metal Reagents in Organic Reactions. Part-VI 1,2. Oxidation of Indoles with Thallium(III) Acetate". . p. 698 - 704. Retrieved 2007/10/03.