3-Indolylacetone

Base Information

• Chemical Name: 3-Indolylacetone
• CAS No.: 1201-26-9
• Molecular Formula: C11H11NO
• Molecular Weight: 173.214
• European Community (EC) Number: 214-855-4
• NSC Number: 100751
• UNII: 0YSP0BPC6X
• DSSTox Substance ID: DTXSID20152676
• Nikkaji Number: J7.453E
• Wikidata: Q27237357
• ChEMBL ID: CHEMBL1597141
• Mol file: 1201-26-9.mol

Synonyms:3-Indolylacetone;Indole-3-acetone;1201-26-9;1-(1H-indol-3-yl)propan-2-one;3-(2-Oxopropyl)indole;2-Propanone, 1-(1H-indol-3-yl)-;Indol-3-yl-2-propanone;2-Propanone, 1-indol-3-yl-;3-acetonylindole;1-(1H-Indol-3-yl)acetone;1-(1H-indol-3-yl)-2-propanone;UNII-0YSP0BPC6X;MFCD00047187;0YSP0BPC6X;MLS001030037;EINECS 214-855-4;1-(1H-Indol-3-yl)-propan-2-one;NSC 100751;NSC-100751;SMR000427279;cid_70989;SCHEMBL468399;3-INDOLYLACETONE [MI];CHEMBL1597141;(1H-INDOL-3-YL)ACETON;BDBM63801;1-(1H-Indol-3-yl)acetone #;DTXSID20152676;AMY33433;BCP26730;NSC100751;STL297877;AKOS005203354;FS-4192;NCGC00182591-01;SY269712;CS-0075666;FT-0615870;I-1190;EN300-1697979;Q27237357;F2167-4308;Z277541166

Chemical Property of 3-Indolylacetone

Chemical Property:

• Appearance/Colour: off-white to light brown crystalline powder
• Vapor Pressure: 7.93E-05mmHg at 25°C
• Melting Point: 115oC ± 2oC
• Refractive Index: 1.629
• Boiling Point: 341.7 °C at 760 mmHg
• Flash Point: 168.4 °C
• PSA: 32.86000
• Density: 1.167 g/cm³
• LogP: 2.29940
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 173.084063974
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

3-Indolylacetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC1=CNC2=CC=CC=C21
• Uses: 3-Indolylacetone is an indole derivative that may act as a benzodiazepine receptor inhibitor.

Technology Process of 3-Indolylacetone

There total 13 articles about 3-Indolylacetone 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: 87.0%

methylmagnesium chloride (676-58-4) + 2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide (132922-37-3) → 3-(1H-indolyl)acetone (1201-26-9)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2004.05.053

Reference yield: 85.0%

α-methyl-β-(3-indolyl)-1-nitroethane (4771-72-6) → 3-(1H-indolyl)acetone (1201-26-9)

Guidance literature:

With hydrogenchloride; iron; In methanol; water; for 0.5h; Heating;

DOI:10.1081/SCC-200051681

Reference yield: 78.0%

3-(2-nitro-propenyl)-1H-indole (84584-89-4) → 3-(1H-indolyl)acetone (1201-26-9)

Guidance literature:

With hydrogenchloride; iron; In methanol; water; for 0.5h; Heating;

DOI:10.1081/SCC-200051681

upstream raw materials:

indole

diazoacetone

cyclohexane

(1-acetyl-indol-3-yl)-acetone

Downstream raw materials:

1-(1H-indol-3-yl)propan-2-amine

(S,S)-N-α-phenetyl-1-indol-3-yl-2-aminopropane

(R)-1-(1H-indol-3-yl)-N-((R)-1-phenylethyl)propan-2-amine

Refernces

• 1、 Banerjee, Ankush,Maji, Modhu Sudan. "A Br?nsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes". . p. 11521 - 11527. Retrieved 2019/08/16.
• 2、 -. "SUBSTITUTED PYRIDO[3,4-B]INDOLES FOR THE TREATMENT OF CARTILAGE DISORDERS". Paragraph 0155. . Retrieved 2018/05/24.