9,10-Epoxy-9,10-dihydrophenanthrene

Base Information

• Chemical Name: 9,10-Epoxy-9,10-dihydrophenanthrene
• CAS No.: 585-08-0
• Deprecated CAS: 84489-06-5,146801-06-1
• Molecular Formula: C14H10 O
• Molecular Weight: 194.233
• DSSTox Substance ID: DTXSID201004762
• Nikkaji Number: J1.636E
• Wikidata: Q27109898
• ChEMBL ID: CHEMBL48158
• Mol file: 585-08-0.mol

Synonyms:9,10-dihydrophenanthrene 9,10-epoxide;9,10-EDPN;9,10-epoxy-9,10-dihydrophenanthrene;9,10-epoxy-9,10-dihydrophenanthrene, (+-)-isomer;phenanthrene 9,10-oxide;phenanthrene-9,10-oxide

Chemical Property of 9,10-Epoxy-9,10-dihydrophenanthrene

Chemical Property:

• Vapor Pressure: 0.000106mmHg at 25°C
• Melting Point: 148°C
• Refractive Index: 1.5920 (estimate)
• Boiling Point: 347.8°C at 760 mmHg
• Flash Point: 158.3°C
• PSA: 12.53000
• Density: 1.246g/cm³
• LogP: 3.47960
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 194.073164938
• Heavy Atom Count: 15
• Complexity: 236

Purity/Quality:

99% ^*data from raw suppliers

9,10-EPOXY-9,10-DIHYDROPHENANTHRENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3C(O3)C4=CC=CC=C42

Technology Process of 9,10-Epoxy-9,10-dihydrophenanthrene

There total 12 articles about 9,10-Epoxy-9,10-dihydrophenanthrene 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: 99.0%

trans-9,10-dihydroxy-3,4-dihydrophenanthrene (25061-61-4) → phenanthrene-9,10-oxide (585-08-0,84489-06-5)

Guidance literature:

With diethoxyltriphenylphosphorane; In dichloromethane; acetonitrile; at 40 ℃; for 48h;

DOI:10.1021/ja00304a030

Reference yield: 96.0%

phenanthrene (85-01-8) + methyltrifluoromethyldioxirane (115464-59-0) → phenanthrene-9,10-oxide (585-08-0,84489-06-5)

Guidance literature:

In dichloromethane; 1,1,2-Trichloro-1,2,2-trifluoroethane; at -20 ℃; for 0.133333h;

DOI:10.1016/S0040-4039(00)98039-0

Reference yield: 95.0%

(+/-)-trans-9-Bromo-10-acetoxy-9,10-dihydrophenanthrene (89523-46-6) → phenanthrene-9,10-oxide (585-08-0,84489-06-5)

Guidance literature:

DOI:10.1016/S0040-4039(01)99806-5

upstream raw materials:

phenanthrene

methyltrifluoromethyldioxirane

(-)-(S,S)-9,10-Dihydroxy-9,10-dihydrophenanthrene

trans-9,10-dihydroxy-3,4-dihydrophenanthrene

Downstream raw materials:

9-Phenanthrol

(3aR,3bS,7S,7aS,8aR)-2,2,5,5-Tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine-7-carboxylic acid 10-phenylsulfanyl-9,10-dihydro-phenanthren-9-yl ester

(R)-4-((3R,5R,8S,9S,10S,13R,14S,17R)-3-Acetoxy-10,13-dimethyl-11-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 10-phenylsulfanyl-9,10-dihydro-phenanthren-9-yl ester

(S)-2-((3S,5S,8S,9S,10S,13S,14S,17R)-3-Acetoxy-10,13-dimethyl-11-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-propionic acid 10-phenylsulfanyl-9,10-dihydro-phenanthren-9-yl ester

Refernces

A New Cyclization Reaction Leading to Epoxides of Aromatic Hydrocarbons

10.1021/ja01078a038

The study explores various chemical reactions and syntheses involving different compounds. One section focuses on the formolysis of alkyl p-nitrobenzenesulfonates, where different substrates like 6-methyl-5-heptenyl p-nitrobenzenesulfonate and 6-methyl-6-heptenyl p-nitrobenzenesulfonate are used to produce various alcohols and olefins. The yields and extents of reactions are analyzed and reported. Another part of the study describes the synthesis of epoxides of aromatic hydrocarbons, such as 9,10-dihydro-9,10-epoxyphenanthrene, 3,4-dihydro-3,4-epoxy-1,2-benzanthracene, and 3,4-dihydro-3,4-epoxy-10-methyl-1,2-benzanthracene, using trisdimethylaminophosphine and dialdehydes. These epoxides are sensitive to acid treatment and rearrange to form phenolic compounds. The study also involves the preparation of 4-bromo- and 4-iodo-2,5,7-trinitrofluorenones as reagents for forming charge-transfer complexes suitable for X-ray analysis. Various complexes are listed, and the study aims to explore the complex-forming abilities of these reagents and their potential use in X-ray crystallographic studies.