Pyrrolnitrin

Base Information

• Chemical Name: Pyrrolnitrin
• CAS No.: 1018-71-9
• Molecular Formula: C10H6 Cl2 N2 O2
• Molecular Weight: 257.076
• Hs Code.: 2933990090
• European Community (EC) Number: 213-812-7
• NSC Number: 637277,107654
• UNII: N0P24B6EDQ
• DSSTox Substance ID: DTXSID9046867
• Nikkaji Number: J7.221D
• Wikipedia: Pyrrolnitrin
• Wikidata: Q371817
• NCI Thesaurus Code: C81509
• Metabolomics Workbench ID: 67631
• ChEMBL ID: CHEMBL97972
• Mol file: 1018-71-9.mol

Synonyms:Pyrrolnitrin

Chemical Property of Pyrrolnitrin

Chemical Property:

• Vapor Pressure: 1.42E-06mmHg at 25°C
• Melting Point: 124.5°
• Refractive Index: 1.6100 (estimate)
• Boiling Point: 410.5°Cat760mmHg
• PKA: 14.28±0.50(Predicted)
• Flash Point: 202.1°C
• PSA: 61.61000
• Density: 1.523g/cm³
• LogP: 4.41990
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 255.9806328
• Heavy Atom Count: 16
• Complexity: 272

Purity/Quality:

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

PYRROLNITRIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)[N+](=O)[O-])C2=CNC=C2Cl
• Uses: Antifungal. Pyrrolnitrin from Pseudomonas cepacia has been used as a standard in the detection of pyrrolnitrin in Serratia marcescens cell culture extract.

Technology Process of Pyrrolnitrin

There total 4 articles about Pyrrolnitrin 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: 74.0%

3-chloro-4-(3'-chloro-2'-nitrophenyl)-N-(TIPS)pyrrole (1126425-93-1) → pyrrolnitrin (1018-71-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; Darkness;

DOI:10.1021/ol8026957

Reference yield:

4-(3'-chloro-2'-aminophenyl)-3-chloropyrrole (16386-65-5) → pyrrolnitrin (1018-71-9)

Guidance literature:

With chloroperoxidase CPO-P; NaOAc-buffer; dihydrogen peroxide; In water; at 30 ℃; for 6h;

Reference yield:

7-chloro-D/L-tryptophan (153-97-9) → pyrrolnitrin (1018-71-9)

Guidance literature:

With Na⁽³⁶⁾Cl; cells of Pseudomonas aureofaciens in glycerinic minimal medium; at 30 ℃; for 120h; measurement of radioactivity;

upstream raw materials:

7-chloro-D/L-tryptophan

4-(3'-chloro-2'-aminophenyl)-3-chloropyrrole

3-chloro-4-(3'-chloro-2'-nitrophenyl)-N-(TIPS)pyrrole

Downstream raw materials:

1-(2',3',3'-triiodoallyl)-3-chloro-4-(3-chloro-2-nitrophenyl)pyrrole

2,4-Dichloro-6-[4,5-dichloro-3-nitro-1-(2,3,3-triiodo-allyl)-1H-pyrrol-2-ylmethyl]-phenol

Refernces

• 1、 Morrison, Matthew D.,Hanthorn, Jason J.,Pratt, Derek A.. "Synthesis of pyrrolnitrin and related halogenated phenylpyrroles". supporting information; experimental part. p. 1051 - 1054. Retrieved 2009/07/18.
• 2、 Kirner, Sabine,Pee, Karl-Heinz van. "Biosynthese von Nitroverbindungen: Die enzymatische Oxidation einer Vorstufe mit Aminogruppe zu Pyrrolnitrin". . p. 346 - 347. Retrieved 2007/10/02.