5-Bromoisatin

Base Information

• Chemical Name: 5-Bromoisatin
• CAS No.: 87-48-9
• Molecular Formula: C8H4BrNO2
• Molecular Weight: 226.029
• Hs Code.: 29337900
• European Community (EC) Number: 201-747-7
• NSC Number: 4980
• DSSTox Substance ID: DTXSID30236037
• Nikkaji Number: J3.901B
• Wikidata: Q72445783
• ChEMBL ID: CHEMBL115897
• Mol file: 87-48-9.mol

Synonyms:5-bromisatin;5-bromoisatin

Chemical Property of 5-Bromoisatin

Chemical Property:

• Appearance/Colour: Orange crystalline powder
• Melting Point: 251-253 °C
• Refractive Index: 1.649
• Boiling Point: 136ºC
• PKA: 8.74±0.20(Predicted)
• PSA: 46.17000
• Density: 1.826 g/cm³
• LogP: 1.72190
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in N,N dimethylformamide.
• 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

5-Bromoisatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36/39-37/39-36

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=O)C(=O)N2
• Uses: Indole derivative 5-Bromoisatin is used in the synthesis of N-derivatives of 5-bromoisatin, N-substituted pyrroles, linear polyaryleneoxindoles, 5-bromodioxindole, cinchoninic acid derivatives, 3-hydroxyoxindole, S-benzyldithiocarbazate Schiff Bases, 5-bromooxindole and Morita-Baylis-Hillman adducts of isatin derivatives. It is an indole derivative.

Technology Process of 5-Bromoisatin

There total 51 articles about 5-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: 96.0%

5-bromo-2-indolin-2-one (20870-78-4) → 5-Bromo-1H-indole-2,3-dione (87-48-9)

Guidance literature:

With oxygen; copper(II) acetate monohydrate; potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 0.5h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2015.02.019

Reference yield: 96.0%

N-(4-bromophenyl)-2-(hydroxyimino) acetamide (66475-83-0) → 5-Bromo-1H-indole-2,3-dione (87-48-9)

Guidance literature:

With sulfuric acid; at 60 - 80 ℃; for 0.166667h;

DOI:10.1016/j.bmcl.2017.06.065

Reference yield: 94.0%

5-bromo-3-iodo-1H-indole (868694-19-3) → 5-Bromo-1H-indole-2,3-dione (87-48-9)

Guidance literature:

With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 25 - 35 ℃; for 7h;

DOI:10.1016/j.tet.2019.02.033

upstream raw materials:

ethanol

N-(4-bromophenyl)-2-(hydroxyimino) acetamide

N-(4-bromo-2-(2,2-dibromoacetyl)phenyl)acetamide

indole-2,3-dione

Downstream raw materials:

6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid

6-bromo-2-(4-chloro-phenyl)-3-methyl-quinoline-4-carboxylic acid

2-biphenyl-4-yl-6-bromo-quinoline-4-carboxylic acid

6-bromo-2-(4-fluorophenyl)-3-methylquinoline-4-carboxylic acid

Refernces

• 1、 Tri, Nguyen Minh,Thanh, Nguyen Dinh,Ha, Luong Ngoc,Anh, Dang Thi Tuyet,Toan, Vu Ngoc,Giang, Nguyen Thi Kim. "Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions". . p. 4793 - 4801. Retrieved 2021/05/31.
• 2、 Burke, Anthony J.,Erxleben, Andrea,Marques, Carolina S.,McArdle, Patrick. "Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction". supporting information. . Retrieved 2020/06/30.