9-Phenanthrol

Base Information

• Chemical Name: 9-Phenanthrol
• CAS No.: 484-17-3
• Molecular Formula: C14H10 O
• Molecular Weight: 194.233
• Hs Code.: 2906299090
• European Community (EC) Number: 207-602-4
• NSC Number: 50554
• UNII: 9FYU45OV9H
• DSSTox Substance ID: DTXSID9047592
• Nikkaji Number: J69.853I
• Wikipedia: 9-Phenanthrol
• Wikidata: Q24063303
• Metabolomics Workbench ID: 51859
• ChEMBL ID: CHEMBL2407182
• Mol file: 484-17-3.mol

Synonyms:9-hydroxyphenanthrene;9-phenanthrol

Chemical Property of 9-Phenanthrol

Chemical Property:

• Vapor Pressure: 4.02E-07mmHg at 25°C
• Melting Point: 139-143oC
• Refractive Index: 1.5920 (estimate)
• Boiling Point: 404.5°C at 760 mmHg
• PKA: 9.40±0.30(Predicted)
• Flash Point: 197.7°C
• PSA: 20.23000
• Density: 1.244g/cm³
• LogP: 3.69860
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 194.073164938
• Heavy Atom Count: 15
• Complexity: 225

Purity/Quality:

97% ^*data from raw suppliers

9-Phenanthrol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C=C(C3=CC=CC=C23)O
• General Description: 9-PHENANTHROL (also known as 9-Hydroxyphenanthrene) is involved in oxygen transfer reactions with flavin hydroperoxide intermediates, leading to the formation of products such as 9,10-phenanthrenequinone. The study highlights its reactivity as a phenolate anion, demonstrating efficient dioxygen transfer from 4a-FlEtO2-, suggesting its role in biomimetic flavoenzyme-like processes. The findings indicate that 9-PHENANTHROL participates in unique oxygen insertion mechanisms, forming dihydrodiol or quinone derivatives under the studied conditions.

Technology Process of 9-Phenanthrol

There total 95 articles about 9-Phenanthrol 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: 98.0%

N,N-diisopropyl-2'-methyl-[1,1'-biphenyl]-2-carboxamide (120270-41-9) → 9-Phenanthrol (484-17-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 0 deg C to rt, 3 h;

DOI:10.1016/S0040-4039(00)80786-8

Reference yield: 97.5%

9-methoxyphenanthrene (5085-74-5) → 9-Phenanthrol (484-17-3)

Guidance literature:

With hydrogenchloride; acetic acid; In water; for 6h; Reagent/catalyst; Reflux;

Reference yield: 95.0%

2-ethynyl-1,1'-biphenyl (52889-62-0) → 9-Phenanthrol (484-17-3)

Guidance literature:

With 2,6-dichloropyridine N-oxide; C₃₃H₅₄AuClP; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; In 1,2-dichloro-ethane; at 50 ℃; for 11h;

DOI:10.1021/acs.joc.7b01244

upstream raw materials:

10-chloro-[9]phenanthrol

cis-9,10-dihydroxy-9,10-dihydrophenanthrene

2'-carboxybiphenyl-2-acetic acid

9-bromo-10-hydroxyphenanthrene

Downstream raw materials:

N,N-diethyl 10-(4'-nitrophenyl)phenanthren-9-yl-O-carbamate

(CO)5W(C₁₇H₉OC₆H₅)

9-methylphenanthrene

9-cyanophenanthrene

Refernces

Dioxygen Transfer from 4a-Hydroperoxyflavin Anion. 2. Oxygen Transfer to the 10 Position of 9-Hydroxyphenanthrene Anions and to 3,5-Di-tert-butylcatechol Anion

10.1021/ja00533a028

The research investigates the reaction mechanisms of oxygen transfer from the peroxy anion of N5-ethyl-4a-hydroperoxy-3-methyllumiflavin (4a-FlEtO2-) to various phenolate anions, aiming to understand the underlying processes and provide insights into biomimetic reactions of flavoenzyme dioxygenase. The study found that 4a-FlEtO2- can transfer both oxygen atoms to phenolate anions, leading to the formation of specific products and regeneration of reduced flavin. Key chemicals involved include 4a-FlEtO2-, phenolate anions such as 3,5-di-tert-butylcatechol (VIII), 10-methyl-9-phenanthrol (Ib), and 10-ethoxy-9-phenanthrol (Ia), and their respective products like 3,5-di-tert-butyl-o-quinone (IX), 10-hydroxy-10-methyl-9,10-dihydro-9-phenanthrone (IIIb), and 9,10-phenanthrenequinone (V). The research concludes that the oxygen-donating intermediate formed from 4a-FlEtO2- is likely a dioxetane or an oxygen molecule loosely associated with the flavin, and the reaction efficiency of 4a-FlEtO2- exceeds that of molecular oxygen by a significant margin, indicating a unique and efficient oxygen transfer mechanism.