4-Bromo-5-methoxyisatin

Base Information

• Chemical Name: 4-Bromo-5-methoxyisatin
• CAS No.: 130420-75-6
• Molecular Formula: C₉H₆BrNO₃
• Molecular Weight: 256.056
• DSSTox Substance ID: DTXSID20433851
• Wikidata: Q82248103
• Mol file: 130420-75-6.mol

Synonyms:4-bromo-5-methoxyisatin;130420-75-6;4-bromo-5-methoxy-1H-indole-2,3-dione;4-BROMO-5-METHOXYINDOLINE-2,3-DIONE;SCHEMBL7815590;DTXSID20433851;ZGBUBQYGLBBQEI-UHFFFAOYSA-N;FT-0696831;EN300-218558;4-bromo-5-methoxy-2,3-dihydro-1H-indole-2,3-dione;Z1726058190

Chemical Property of 4-Bromo-5-methoxyisatin

Chemical Property:

• PSA: 55.40000
• LogP: 1.73050
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 254.95311
• Heavy Atom Count: 14
• Complexity: 281

Purity/Quality:

98% ^*data from raw suppliers

4-Bromo-5-methoxyisatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(C=C1)NC(=O)C2=O)Br

Technology Process of 4-Bromo-5-methoxyisatin

There total 4 articles about 4-Bromo-5-methoxyisatin 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: 27.0%

N-(3-Bromo-4-methoxy-phenyl)-2-[(Z)-hydroxyimino]-acetamide (130420-84-7) → 6-bromo-5-methoxy-indoline-2,3-dione (130420-78-9) + 4-bromo-5-methoxyisatin (130420-75-6)

Guidance literature:

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

Reference yield: 25.0%

(2E)-N-(3-bromo-4-methoxy-phenyl)-2-hydroxyiminoacetamide → 6-bromo-5-methoxy-indoline-2,3-dione (130420-78-9) + 4-bromo-5-methoxyisatin (130420-75-6)

Guidance literature:

With sulfuric acid; at 65 - 70 ℃;

DOI:10.1021/jm00058a010

Reference yield:

3-bromo-p-anisidine (19056-41-8) → 4-bromo-5-methoxyisatin (130420-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / sodium sulfate, conc. HCl, hydroxylamine hydrochloride / H₂O / Heating

2: 25 percent / conc. H₂SO₄ / 65 - 70 °C

With hydrogenchloride; sulfuric acid; hydroxylamine hydrochloride; sodium sulfate; In water;

DOI:10.1021/jm00058a010

upstream raw materials:

N-(3-Bromo-4-methoxy-phenyl)-2-[(Z)-hydroxyimino]-acetamide

3-bromo-p-anisidine

3-bromo-4-methoxy-phenylamine hydrochloride

Downstream raw materials:

6-amino-2-bromo-3-methoxybenzoic acid

4-bromo-5-methoxy-1-morpholinomethylisatin

Refernces

• 1、 Webber,Bleckman,Attard,Deal,Kathardekar,Welsh,Webber,Janson,Matthews,Smith,Freer,Jordan,Bacquet,Howland,Booth,Ward,Hermann,White,Morse,et al.. "Design of thymidylate synthase inhibitors using protein crystal structures: The synthesis and biological evaluation of a novel class of 5- substituted quinazolinones". . p. 733 - 746. Retrieved 2007/10/02.