15679-03-5

Basic information

• Product Name: 6-chlorophenanthridine
• Synonyms: 6-chlorophenanthridine;MFCD01628084
• CAS NO: 15679-03-5
• Molecular Formula: C₁₃H₈ClN
• Molecular Weight: 213.67
• Mol File: 15679-03-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 117-118 °C
• Boiling Point: 377.7 °C at 760 mmHg
• Flash Point: 214.1 °C
• Appearance: /
• Density: 1.312 g/cm³
• Vapor Pressure: 1.44E-05mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.36±0.40(Predicted)
• CAS DataBase Reference: 6-chlorophenanthridine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chlorophenanthridine(15679-03-5)
• EPA Substance Registry System: 6-chlorophenanthridine(15679-03-5)

Safety Data

• Hazardous Substances Data: 15679-03-5(Hazardous Substances Data)

Usage

General Description

6-chlorophenanthridine is a chemical compound with the molecular formula C14H9ClN. It is a heterocyclic aromatic compound and a derivative of phenanthridine. This yellowish crystalline solid is mainly used as a building block in the synthesis of various pharmaceuticals and organic compounds. It is known for its potential antimicrobial, anticancer, and anti-inflammatory properties, making it a valuable compound in drug discovery and development. 6-chlorophenanthridine is also widely studied for its potential use as an antifungal agent and in the treatment of various diseases. Due to its structural and biological properties, this chemical has attracted significant research interest in the fields of medicinal chemistry and pharmacology.

InChI:InChI=1/C13H8ClN/c14-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)15-13/h1-8H

Upstream product

• 1015-89-0 6(5H)-phenanthridinone 
• 229-87-8 phenanthridine 
• 6747-35-9 2-carboxy-2'-(aminocarboxyl)-1,1'-biphenyl 
• 90-41-5 2-phenylaniline 
• 115293-14-6 1,3-di(biphenyl-2-yl)urea 
• 138344-50-0 tert-butyl [1,1′-biphenyl]-2-ylcarbamate 
• 17337-13-2 [1,1'-biphenyl]-2-yl-isocyanate 
• 1015-89-0 phenanthridin-6-ol 
• 79-37-8 oxalyl dichloride 
• 2157-52-0 9-fluorenone oxime 
• 486-25-9 9-fluorenone 
• 173379-08-3 1,1'-biphenyl-2-yl isocyanide dibromide 
• 3128-77-6 2-isocyanobiphenyl 
• 15999-44-7 1,1'-biphenyl-2-yl isocyanide dichloride 

Downstream Products

• 23165-19-7 4,4-dimethylmorpholinium chloride 
• 3340-87-2 6-phenoxyphenanthridine 
• 832-68-8 6-aminophenanthridine 
• 130137-90-5 Phenanthridin-6-yl-(4-phenyl-furazan-3-yl)-amine 
• 82937-37-9 2-nitro-N-(phenanthridin-6-yl)aniline 
• 846-62-8 6-anilinophenanthridine 
• 66151-98-2 Phenanthridin-6-yl-m-tolyl-amine 
• 142138-63-4 Phenanthridin-6-yl-o-tolyl-amine 
• 78256-30-1 2-nitrophenanthridin-6(5H)-one 
• 23818-43-1 4-nitro-6(5H)-phenanthridinone 
• 144402-92-6 6-hydrazinophenanthridine 
• 23441-13-6 6-(4-methyl-piperazyl)-phenanthridine 
• 130137-92-7 2-benzoyl-1,2,4-triazolo<1,5-f>phenanthridine Z-oxime 
• 130137-93-8 2-benzoyl-1,2,4-triazolo<1,5-f>phenanthridine E-oxime 

Relevant articles and documents

Novel phenanthridine amide analogs as potential anti-leishmanial agents: In vitro and in silico insights

In the current work, sixteen novel amide derivatives of phenanthridine were designed and synthesized using 9-fluorenone, 4-Methoxy benzyl amine, and alkyl/aryl acids. The characterization of the title compounds was performed using LCMS, elemental analysis, 1HNMR, 13CNMR and single crystal XRD pattern was also developed for compounds A8. All the final analogs were screened in vitro for anti-leishmanial activity against promastigote form of L. infantum strain. Among the tested analogs, four compounds (A-06, A-11, A-12, and A-15) exhibited significant anti-leishmanial activity with EC50 value ranges from 8.9 to 21.96 μM against amastigote forms of tested L. infantum strain with SI ranges of 1.0 to 4.3. From the activity results it was found that A-11 was the most active compound in both promastigote and amastigotes forms with EC50 values 8.53 and 8.90 μM respectively. In-silico ADME prediction studies depicted that the titled compounds obeyed Lipinski's rule of five as that of the approved marketed drugs. The predicted in-silico toxicity profile also confirmed that the tested compounds were non-toxic. Finally, molecular docking and molecular dynamics study was also performed for significantly active compound (A-11) in order to study it's putative binding pattern at the active site of the selected leishmanial trypanothione reductase target as well as to understand the stability pattern of target-ligand complex for 100 ns. Single crystal XRD of compound A-08 revealed that the compound crystallizes in monoclinic C2/c space group and showed interesting packing arrangements.

Application of phenanthridine compounds to pesticides

The invention relates to an application of phenanthridine compounds shown in general formula (1) to pesticides. Part of the compounds is used as a plant virus agent and can well inhibit the tobacco mosaic virus; when used as a bactericide, the compounds have good inhibitory activity on tomato early blight, wheat scab, potato late blight, phytophthora capsici, rape sclerotinia rot, cucumber gray mould, rice sheath blight disease, cucumber fusarium wilt, cercospora brown spot of peanut, apple ring rot, wheat sharp eyespot, corn southern leaf blight, watermelon anthracnose and rice bakanae disease; when used as an insecticide, the compounds have poisonous activity on armyworms, mosquito larvae, cotton bollworms, ostrinia nubilalis, aphids, adult mites and plutella xylostella. In the formula,when molecular nitrogen is not imine, R can represent hydrogen atoms, methyl, acetyl and benzoyl; R and R represent a hydrogen atom or an oxygen atom simultaneously; R and R can represent hydroxyl, acetoxyl, methoxyl, methyleneoxy, a fluorine atom and the hydrogen atom; R is a bromine atom or the fluorine atom; R is the hydrogen atom or vinyl. When nitrogen is imine, R doesnot represent any group; one of R and R does not represent any group, and the other can represent the hydrogen atom, methoxyl, ethyoxyl, benzyloxy and a chlorine atom; R, R, R and Rrepresent the hydrogen atom.

Synthesis method of 6-chlorophenanthridine

The invention belongs to the fields of synthesis of medicines and materials and in particular relates to a synthesis method of 6-chlorophenanthridine. The synthesis method comprises the following two steps: firstly, carrying out reaction on formic acid and acetic anhydride, then reacting with 2-aminobiphenyl to generate an intermediate I; and secondly, reacting the obtained intermediate I with chloride and lewis acid to obtain 6-chlorophenanthridine. The synthesis method provided by the invention has the advantages that operation for preparing 6-chlorophenanthridine is easier, and safety factor is high, so that the synthesis method is especially applicable to industrial production.