cis-9,10-Dihydrophenanthrene-9,10-diol

Base Information

• Chemical Name: cis-9,10-Dihydrophenanthrene-9,10-diol
• CAS No.: 2510-71-6
• Molecular Formula: C14H12 O2
• Molecular Weight: 212.248
• DSSTox Substance ID: DTXSID301242159
• Nikkaji Number: J69.566A
• Wikidata: Q27117154
• Metabolomics Workbench ID: 55585
• Mol file: 2510-71-6.mol

Synonyms:cis-9,10-dihydrophenanthrene-9,10-diol;cis-9,10-Dihydroxy-9,10-dihydrophenanthrene;2510-71-6;(9R,10S)-9,10-dihydrophenanthrene-9,10-diol;(9S,10R)-9,10-dihydrophenanthrene-9,10-diol;cis-9,10-Dihydro-9,10-phenanthrenediol;SCHEMBL6903531;CHEBI:37471;DTXSID301242159;cis-Phenanthrene, 9,10-dihydro-9,10-diol;9,10-Dihydro-9alpha,10alpha-phenanthrenediol;9,10-Phenanthrenediol, 9,10-dihydro-, cis-;Q27117154;rel-(9R,10S)-9,10-Dihydro-9,10-phenanthrenediol

Chemical Property of cis-9,10-Dihydrophenanthrene-9,10-diol

Chemical Property:

• Vapor Pressure: 2.85E-07mmHg at 25°C
• Melting Point: >170°C (dec.)
• Boiling Point: 404.6°C at 760 mmHg
• Flash Point: 200.5°C
• PSA: 40.46000
• Density: 1.326g/cm³
• LogP: 2.43400
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 212.083729621
• Heavy Atom Count: 16
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

cis-9,10-Dihydroxy-9,10-dihydrophenanthrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C(C3=CC=CC=C32)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)[C@@H]([C@@H](C3=CC=CC=C32)O)O
• Uses: A dihydroxy metabolite of Phenanthrene with cis conformation. Produced via degradation by phenoloxidases and dioxygenases of Polyporus sp. S133.

Technology Process of cis-9,10-Dihydrophenanthrene-9,10-diol

There total 6 articles about cis-9,10-Dihydrophenanthrene-9,10-diol 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: 92.0%

ortho-bromobenzaldehyde (6630-33-7) → cis-9,10-dihydroxy-9,10-dihydrophenanthrene (2510-71-6) + Biphenyl-2,2'-dicarbaldehyde (1210-05-5)

Guidance literature:

With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,5-cis,cis-cyclooctadiene; In N,N-dimethyl-formamide; at 20 - 60 ℃; for 3.3h;

DOI:10.1021/jo9817523

Reference yield:

trans-9-bromo-10-hydroxy-9,10-dihydrophenanthrene → 9-Phenanthrol (484-17-3) + cis-9,10-dihydroxy-9,10-dihydrophenanthrene (2510-71-6) + 9,10-phenanthrenequinone (84-11-7)

Guidance literature:

at 25 ℃; pH=4.55; aq. acetate buffer;

DOI:10.1021/ol1014027

Reference yield:

cis-9-(trichloroacetoxy)-10-hydroxy-9,10-dihydrophenanthrene → 9-Phenanthrol (484-17-3) + cis-9,10-dihydroxy-9,10-dihydrophenanthrene (2510-71-6) + 9,10-phenanthrenequinone (84-11-7)

Guidance literature:

In water; acetonitrile; at 25 ℃;

DOI:10.1021/ol1014027

upstream raw materials:

ortho-bromobenzaldehyde

phenanthrene

tetrachloromethane

Downstream raw materials:

9-Phenanthrol

6H-benzo[c]chromen-6-one

diphenic acid

9,10-phenanthrenequinone