Pentabromopseudilin

Base Information

• Chemical Name: Pentabromopseudilin
• CAS No.: 10245-81-5
• Molecular Formula: C10H4 Br5 N O
• Molecular Weight: 553.668
• Hs Code.: 2933990090
• NSC Number: 641543,288032
• UNII: BUV7D4FJ9V
• DSSTox Substance ID: DTXSID90314744
• Nikkaji Number: J83.298G
• Wikipedia: Pentabromopseudilin
• Wikidata: Q27138952
• Metabolomics Workbench ID: 122980
• ChEMBL ID: CHEMBL1235156
• Mol file: 10245-81-5.mol

Synonyms:2,3,4-tribromo-5-(3,5-dibromo-2-hydroxyphenyl)-1H-pyrrole;pentabromopseudilin

Chemical Property of Pentabromopseudilin

Chemical Property:

• Vapor Pressure: 3.07E-09mmHg at 25°C
• Boiling Point: 464.2°C at 760 mmHg
• Flash Point: 234.5°C
• PSA: 36.02000
• Density: 2.606g/cm³
• LogP: 6.19980
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 552.61688
• Heavy Atom Count: 17
• Complexity: 281

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pentabromopseudilin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1C2=C(C(=C(N2)Br)Br)Br)O)Br)Br
• Uses: Pentabromopseudilin, is a metabolite produced by Chromobacterium, isolated from a seawater sample from the North Pacific Gyre. The compound as shown to be responsible for autoinhibition in the Chromobacterium itself, as well as for antibiotic action against other kinds of bacteria.

Technology Process of Pentabromopseudilin

There total 36 articles about Pentabromopseudilin 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: 86.0%

3,4,5-Tribrom-2-(3',5'-dibrom-2'-methoxyphenyl)-1H-pyrrol (10245-83-7) → 2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol (10245-81-5)

Guidance literature:

With boron tribromide; In dichloromethane; at -20 ℃; for 12h;

Reference yield: 68.0%

2-(2-hydroxyphenyl)-1H-pyrrole (42041-50-9) → 2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol (10245-81-5)

Guidance literature:

With pyridinium hydrobromide perbromide; In ethanol; for 65h; Ambient temperature;

DOI:10.1021/jo9723063

Reference yield:

allyl-[1-(2-benzyloxy-phenyl)-prop-2-ynyl]-carbamic acid methyl ester (856438-49-8) → 2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol (10245-81-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: quinoline; H₂ / Pd/BaSO₄ / ethyl acetate / 0.33 h

1.2: 81 percent / Grubbs second generation ruthenium catalyst / CH₂Cl₂ / 18 h / 20 °C

2.1: 63 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / toluene / 48 h / 110 °C

3.1: 95 percent / NaOH / ethanol / 0.58 h / 20 °C

4.1: 80 percent / liquid ammonia; Na / tetrahydrofuran / -78 °C

5.1: 52 percent / pyridinium tribromide / ethanol / 55 h / 20 °C

With quinoline; sodium hydroxide; ammonia; hydrogen; sodium; pyridinium hydrobromide perbromide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Pd-BaSO₄; In tetrahydrofuran; ethanol; ethyl acetate; toluene;

DOI:10.1021/ol050897a

upstream raw materials:

3,4,5-Tribrom-2-(3',5'-dibrom-2'-methoxyphenyl)-1H-pyrrol

2-(2-hydroxyphenyl)-1H-pyrrole

2-(2-benzyloxyphenyl)-1H-pyrrole

4-(2-(benzyloxy)phenyl)-4-oxobutanal

Downstream raw materials:

3,4,5-Tribrom-2-(3',5'-dibrom-2'-methoxyphenyl)-1H-pyrrol

diphenyldisulfane

Refernces

• 1、 Kumar, Mukesh,Sharma, Shweta,Sil, Parijat,Kushwaha, Manoj,Mayor, Satyajit,Vishwakarma, Ram A.,Singh, Parvinder Pal. "C–H Arylation of N-Heteroarenes under Metal-Free Conditions and its Application towards the Synthesis of Pentabromo- and Pentachloropseudilins". supporting information. p. 3591 - 3598. Retrieved 2019/06/20.
• 2、 Schwalm, Cristiane S.,De Castro, Ilton B.D.,Ferrari, Jailton,De Oliveira, Fábio L.,Aparicio, Ricardo,Correia, Carlos Roque D.. "Synthesis of pentabromopseudilin and other arylpyrrole derivatives via Heck arylations". supporting information; experimental part. p. 1660 - 1663. Retrieved 2012/04/10.