5960-69-0

Basic information

• Product Name: 2-ACETYLPHENANTHRENE
• Synonyms: 2-ACETYLPHENANTHRENE;1-(2-Phenanthryl)ethanone;Ethanone, 1-(2-phenanthrenyl)-;methyl 2-phenanthryl ketone;1-(phenanthren-2-yl)ethan-1-one;1-(phenanthren-2-yl)ethanone
• CAS NO: 5960-69-0
• Molecular Formula: C₁₆H₁₂O
• Molecular Weight: 220.27
• EINECS: 227-730-4
• Product Categories: C15 to C38;Carbonyl Compounds;Ketones
• Mol File: 5960-69-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 144-145 °C(lit.)
• Boiling Point: 405.9 °C at 760 mmHg
• Flash Point: 180.7 °C
• Appearance: solid
• Density: 1.164 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 2-ACETYLPHENANTHRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETYLPHENANTHRENE(5960-69-0)
• EPA Substance Registry System: 2-ACETYLPHENANTHRENE(5960-69-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5960-69-0(Hazardous Substances Data)

Usage

Description

2-Acetylphenanthrene is an organic compound with the molecular formula C14H10O. It is a derivative of phenanthrene, featuring an acetyl group attached to the second carbon atom. 2-ACETYLPHENANTHRENE is known for its distinct chemical properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
2-Acetylphenanthrene is used as a reagent for the synthetic preparation of anti-staphylococcal Celecoxib (C251000) derivatives. Celecoxib is a nonsteroidal anti-inflammatory drug (NSAID) that is effective in treating various conditions, such as pain, inflammation, and fever. 2-ACETYLPHENANTHRENE plays a crucial role in the development of these pharmaceutical products by facilitating the synthesis of the active ingredients.
Chemical Properties:
2-Acetylphenanthrene exhibits a melting point of 144-145°C, which is an important physical property that can be used to characterize and identify the compound. This information is valuable for researchers and chemists working with 2-acetylphenanthrene in various applications, including synthesis, purification, and quality control processes.

InChI:InChI=1S/C16H12O/c1-11(17)13-8-9-16-14(10-13)7-6-12-4-2-3-5-15(12)16/h2-10H,1H3

Upstream product

• 5329-89-5 2-acetyl-9,10-dihydrophenanthrene 
• 85-01-8 phenanthrene 
• 75-36-5 acetyl chloride 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 108-24-7 acetic anhydride 
• 7664-39-3 hydrogen fluoride 
• 98-95-3 nitrobenzene 
• 5960-77-0 1-[2]phenanthryl-ethanone oxime 

Downstream Products

• 3674-74-6 2-ethylphenanthrene 
• 5756-23-0 (E)-1-(phenanthren-2-yl)-3-phenylprop-2-en-1-one 
• 40452-20-8 phenanthrene-2-carboxylic acid 
• 50558-54-8 1-[2]phenanthryl-3-phenyl-propenone 
• 40452-15-1 2-(2-phenanthryl)propanal 
• 50558-60-6 15-Phenyl-15,16-dihydro-cyclopenta[a]phenanthren-17-one 
• 50512-24-8 4'-Dimethylamino-2-phenanthrylchalcon 
• 32060-67-6 9,10-dioxo-9,10-dihydro-phenanthrene-2-carboxylic acid 
• 79161-76-5 4-Phenanthren-2-yl-2-phenyl-2,3-dihydro-benzo[b][1,4]thiazepine 
• 79161-81-2 3-(2-Amino-phenylsulfanyl)-1-phenanthren-2-yl-3-phenyl-propan-1-one 
• 2606-54-4 2-phenanthrylmethanol 
• 25308-63-8 methyl phenanthrene-2-carboxylate 
• 104931-61-5 (4-Methoxy-phenyl)-[1-phenanthren-2-yl-meth-(E)-ylidene]-amine 
• 104931-62-6 (4-Ethoxy-phenyl)-[1-phenanthren-2-yl-meth-(E)-ylidene]-amine 

Relevant articles and documents

A combined experimental and computational study on the cycloisomerization of 2-ethynylbiaryls catalyzed by dicationic arene ruthenium complexes

Ruthenium-catalyzed cycloisomerization of 2-ethynylbiaryls was investigated to identify an optimal ruthenium catalyst system. A combination of [η6-(p-cymene)RuCl2(PR3)] and two equivalents of AgPF6 effectively converted 2-ethynylbiphenyls into phenanthrenes in chlorobenzene at 120 °C over 20 h. Moreover, 2-ethynylheterobiaryls were found to be favorable substrates for this ruthenium catalysis, thus achieving the cycloisomerization of previously unused heterocyclic substrates. Moreover, several control experiments and DFT calculations of model complexes were performed to propose a plausible reaction mechanism.

Is the Hoveyda-Grubbs complex a vinylogous fischer-type carbene? Aromaticity-controlled activity of ruthenium metathesis catalysts

Three naphthalene-based analogues (4a-c) of the Hoveyda-Grubbs metathesis catalyst exhibited immense differences in reactivity. Systematic structural and spectroscopic studies revealed that the ruthenafurane ring present in all 2-isopropoxyarylidene chelates possesses some aromatic character, which inhibits catalyst activity. This aromatic stabilization within the chelate ring may be controlled by variation of the polycyclic core topology as was demonstrated for tetraline and phenanthrene derivatives (4d,e). General conclusions about a new mode of ligand-structure tuning in catalytic systems are presented.

On the Acetylation of Phenanthrene and 9-Chlorphenanthrene

Friedel-Crafts acetylation of phenanthrene (1a) in sym-tetrachlorethane yields mixtures of 2-,3- and 9-acetylphenanthrenes (2a,3a,4).The distribution of isomers is found to depend strongly upon the method of mixing the reagents.Acetylation of 9-chlorophenanthrene (1b), perfomed by a variety of methods and solvents, led mainly to 3-acetyl-9-chlorophenanthrene (3b) (>/=85percent).Previously unreported 2-acetyl-9-chlorophenanthrene (2b) was found to form up to a maximum 11percent in nitrobenzene.