6-Bromoisatin

Base Information

• Chemical Name: 6-Bromoisatin
• CAS No.: 6326-79-0
• Molecular Formula: C8H4BrNO2
• Molecular Weight: 226.029
• Hs Code.: 2933990090
• European Community (EC) Number: 678-162-2
• NSC Number: 30748
• UNII: UVA4QW7PH2
• DSSTox Substance ID: DTXSID50212651
• Nikkaji Number: J1.262.653C
• Wikidata: Q72445785
• ChEMBL ID: CHEMBL223335
• Mol file: 6326-79-0.mol

Synonyms:Indole-2,3-dione,6-bromo- (8CI);6-Bromo-1H-indole-2,3-dione;6-Bromoindole-2,3-dione;6-Bromoindoline-2,3-dione;6-Bromoisatin;NSC 30748;

Chemical Property of 6-Bromoisatin

Chemical Property:

• Appearance/Colour: Orange powder
• Melting Point: 274 °C
• Refractive Index: 1.649
• PKA: 8.83±0.20(Predicted)
• PSA: 46.17000
• Density: 1.826 g/cm³
• LogP: 1.72190
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 224.94254
• Heavy Atom Count: 12
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

6-BromoIsatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-41-43
• Safety Statements: 22-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)NC(=O)C2=O
• Uses: Antimicrobial

Technology Process of 6-Bromoisatin

There total 5 articles about 6-Bromoisatin 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: 85.0%

6-bromo-2,3-dihydro-1H-indole-2-one (99365-40-9) → 6-bromoisatin (6326-79-0) + 1,1'-dihydro-6,6'-dibromoisoindigo (1147124-21-7)

Guidance literature:

With oxygen; sodium iodide; In tetrahydrofuran; at 60 ℃; for 12h; chemoselective reaction; Schlenk technique;

DOI:10.1039/c8cc04471f

Reference yield: 83.0%

N-(3-bromophenyl)-2-(hydroxyimino)ethanamide (65971-74-6) → 6-bromoisatin (6326-79-0) + 4-bromoisatin (20780-72-7)

Guidance literature:

N-(3-bromophenyl)-2-(hydroxyimino)ethanamide; With sulfuric acid; at 50 - 80 ℃; for 0.333333h;

With water; at 0 ℃; for 1h;

Reference yield: 27.0%

(E)-N-(3-bromophenyl)-2-(hydroxyimino)acetamide (65971-74-6) → 6-bromoisatin (6326-79-0) + 4-bromoisatin (20780-72-7)

Guidance literature:

With sulfuric acid; at 60 - 80 ℃; for 0.75h;

upstream raw materials:

(E)-N-(3-bromophenyl)-2-(hydroxyimino)acetamide

N-(3-bromophenyl)-2-(hydroxyimino)ethanamide

chloral hydrate

m-Bromoaniline

Downstream raw materials:

2-amino-4-bromobenzoic acid

tyrian purple

6-bromo-1H-indazole-3-carboxylic acid methyl ester

6-bromo-1H-indazole-3-carboxylic acid

Refernces

• 1、 Zhang, Hong-Hua,Wang, Yong-Qiang,Huang, Long-Tao,Zhu, Long-Qing,Feng, Yi-Yue,Lu, Ying-Mei,Zhao, Quan-Yi,Wang, Xue-Qiang,Wang, Zhen. "NaI-mediated divergent synthesis of isatins and isoindigoes: A new protocol enabled by an oxidation relay strategy". supporting information. p. 8265 - 8268. Retrieved 2018/07/29.
• 2、 Lindsay-Scott, Peter J.,Barlow, Helen. "Utilizing Solubility differences to achieve regiocontrol in the synthesis of substituted quinoline-4-carboxylic acids". supporting information. p. 1516 - 1520. Retrieved 2016/06/14.