9,10-Dihydrophenanthrene

Base Information

• Chemical Name: 9,10-Dihydrophenanthrene
• CAS No.: 776-35-2
• Molecular Formula: C14H12
• Molecular Weight: 180.249
• Hs Code.: 2902909090
• European Community (EC) Number: 212-278-2
• NSC Number: 60018
• UNII: BRM9TU2F34
• DSSTox Substance ID: DTXSID20228264
• Nikkaji Number: J12.473G
• Wikidata: Q27274840
• Metabolomics Workbench ID: 128851
• ChEMBL ID: CHEMBL2407181
• Mol file: 776-35-2.mol

Synonyms:9,10-DIHYDROPHENANTHRENE;776-35-2;Phenanthrene, 9,10-dihydro-;9,10-dihydro-phenanthrene;UNII-BRM9TU2F34;BRM9TU2F34;EINECS 212-278-2;NSC 60018;NSC-60018;NSC60018;CHEMBL2407181;DTXSID20228264;9,10-Dihydrophenanthrene, 94%;MFCD00001164;AKOS004904703;SB66447;AM20041165;D0554;FT-0600670;D89679;A839150;W-203782;Q27274840

Chemical Property of 9,10-Dihydrophenanthrene

Chemical Property:

• Appearance/Colour: dark brown crystals
• Vapor Pressure: 0.00129mmHg at 25°C
• Melting Point: 30-35 °C(lit.)
• Refractive Index: 1.642-1.644
• Boiling Point: 307.8 °C at 760 mmHg
• Flash Point: 144.1 °C
• PSA: 0.00000
• Density: 1.085 g/cm³
• LogP: 3.45220
• Storage Temp.: Refrigerator
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 180.093900383
• Heavy Atom Count: 14
• Complexity: 174

Purity/Quality:

99% ^*data from raw suppliers

9,10-Dihydrophenanthrene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1CC2=CC=CC=C2C3=CC=CC=C31

Technology Process of 9,10-Dihydrophenanthrene

There total 154 articles about 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: 77.0%

phenylacetylene (536-74-3) + 2-bromobenzylzinc(II) bromide (307496-27-1) → 9,10-dihydroanthracene (613-31-0) + 9,10-dihydrophenanthrene (776-35-2) + 2-phenylindene (4505-48-0)

Guidance literature:

bis(triphenylphosphine)nickel(II) diiodide; In dichloromethane; at 40 ℃; for 6h;

DOI:10.1021/ol702167t

Reference yield: 51.0%

1-Bromo-2-bromomethyl-benzene (3433-80-5) → 2-methylphenyl bromide (95-46-5) + phenanthrene (85-01-8) + 9,10-dihydrophenanthrene (776-35-2) + 1,2-bis(2-bromophenyl)ethane (59485-34-6)

Guidance literature:

With magnesium; at 600 ℃;

Reference yield: 40.0%

2-(chloromethyl)iodobenzene (59473-45-9) → ortho-methylphenyl iodide (615-37-2) + phenanthrene (85-01-8) + 9,10-dihydrophenanthrene (776-35-2) + 1,1'-(1,2-Ethylenediyl)bis(2-iodobenzene) (2582-56-1)

Guidance literature:

With magnesium; at 600 ℃;

upstream raw materials:

phenanthrene

2,2'-bis-(bromomethyl)-1,1'-biphenyl

2-(2-phenylethyl)aniline

1,1'-(1,2-Ethylenediyl)bis(2-iodobenzene)

Downstream raw materials:

4-(9,10-dihydro-[2]phenanthryl)-4-oxo-butyric acid

1-(9,10-dihydro-[2]phenanthryl)-propan-1-one

phenanthrene

2-acetyl-9,10-dihydrophenanthrene

Refernces

Thermal decomposition of O-benzyl ketoximes; role of reverse radical disproportionation

10.1039/b313491a

The research examines the thermal decomposition of various O-benzyl ketoxime ethers (R1R2C(NOCH2Ph)) in three hydrogen donor solvents: tetralin, 9,10-dihydrophenanthrene (DHP), and 9,10-dihydroanthracene (DHA). The study aims to understand the dominant homolytic cleavage modes and the effects of substituents and solvents on the dissociation processes. The results show that the yields of products like imines and benzyl alcohol varied with the solvent, indicating significant involvement of reverse radical disproportionation (RRD) in DHP and DHA, where hydrogen atoms from the solvent transfer to the oxime ethers, followed by β-scission of the resultant radicals. In tetralin, an additional product, benzaldehyde, was observed, suggesting an alternative decomposition mode involving benzylic hydrogen abstraction. The study concludes that the RRD process plays a crucial role in the thermal decomposition of these oxime ethers in certain solvents, and the rates of decomposition and product yields are influenced by both the nature of the substituents and the solvent used.

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