Indoxole

Base Information

• Chemical Name: Indoxole
• CAS No.: 5034-76-4
• Molecular Formula: C22H19 N O2
• Molecular Weight: 329.398
• Hs Code.: 2933990090
• NSC Number: 82959
• UNII: Q0CKS2CL3G
• DSSTox Substance ID: DTXSID70198382
• Nikkaji Number: J8.799H
• Wikidata: Q27286852
• NCI Thesaurus Code: C174859
• ChEMBL ID: CHEMBL2104332
• Mol file: 5034-76-4.mol

Synonyms:2,3-bis(4-methoxyphenyl)indole;indoxole

Chemical Property of Indoxole

Chemical Property:

• Vapor Pressure: 4.92E-10mmHg at 25°C
• Melting Point: 151-152 °C
• Boiling Point: 510.5°C at 760 mmHg
• PKA: 16.81±0.30(Predicted)
• Flash Point: 180.8°C
• PSA: 34.25000
• Density: 1.174g/cm³
• LogP: 5.51910
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 329.141578849
• Heavy Atom Count: 25
• Complexity: 412

Purity/Quality:

99% ^*data from raw suppliers

INDOXOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=C(NC3=CC=CC=C32)C4=CC=C(C=C4)OC
• Uses: Antipyretic; anti-inflammatory.

Technology Process of Indoxole

There total 32 articles about Indoxole 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: 95.0%

2,3-bis(4-methoxyphenyl)-1-(phenylsulfonyl)indole (321896-79-1) → indoxole (5034-76-4)

Guidance literature:

With magnesium; In methanol;

DOI:10.1016/S0040-4039(00)01564-1

Reference yield: 91.0%

4,4'-dimethoxydiphenylacetylene (2132-62-9) + 1-acetyl-2-phenylhydrazine (114-83-0) → indoxole (5034-76-4)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; acetic acid; In 1,2-dichloro-ethane; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201306098

Reference yield: 90.0%

4,4'-dimethoxydiphenylacetylene (2132-62-9) + phenylhydrazine hydrochloride (59-88-1) → indoxole (5034-76-4)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate; isobutyraldehyde; In methanol; at 80 ℃; for 12h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201304302

upstream raw materials:

2,3-bis(4-methoxyphenyl)-1-(phenylsulfonyl)indole

4-methoxyphenylboronic acid

trimethylsilylacetylene

4-chloromethoxybenzene

Downstream raw materials:

2,3-bis-(4-acetoxy-phenyl)-indole

2,3-bis(4-methoxyphenyl)-1-methyl-1H-indole

4,4'-(1H-indole-2,3-diyl)diphenol

1-ethyl-2,3-bis(4-methoxyphenyl)-1H-indole

Refernces

• 1、 Wang, Jiwei,Wang, Gendi,Cheng, Xiang,Liu, Ye,Zhang, Jun. "Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles". supporting information. p. 1329 - 1333. Retrieved 2021/02/26.
• 2、 Bzeih, Tourin,Zhang, Kena,Khalaf, Ali,Hachem, Ali,Alami, Mouad,Hamze, Abdallah. "One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles". . p. 228 - 238. Retrieved 2019/01/04.