2039-76-1

Usage

Uses

Used in Chemical Synthesis:
3-Acetylphenanthrene is used as a key intermediate in the synthesis of various organic compounds, particularly those with pharmaceutical and industrial applications. Its unique structure allows for further functionalization and modification, making it a versatile building block in organic chemistry.
Used in Environmental Research:
As a derivative of phenanthrene, 3-acetylphenanthrene is utilized in environmental research to study the behavior, distribution, and impact of PAHs in the environment. Understanding the properties and effects of such compounds can help in developing strategies for pollution control and mitigation.
Used in Analytical Chemistry:
3-Acetylphenanthrene can be employed as a reference compound in analytical chemistry for the calibration of instruments and methods used in the detection and quantification of PAHs. Its distinct chemical properties make it suitable for validating the accuracy and precision of analytical techniques.
Used in Material Science:
The unique structure of 3-acetylphenanthrene may also find applications in material science, particularly in the development of novel materials with specific properties. Its potential use in the synthesis of advanced materials, such as conductive polymers or optoelectronic devices, is an area of ongoing research and development.

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

Synthetic route

6-Acetyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one → 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
palladium on activated charcoal at 300℃; for 4.5h;	73%

4-acetylstilbene (3112-03-6) → 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
With potassium iodide In cyclohexane for 3.75h; Irradiation;	43%

1-(5-bromo-2-iodophenyl)ethanone (1261648-81-0) → 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; potassium carbonate; palladium dichloride In N,N-dimethyl-formamide at 150℃; for 3h; Inert atmosphere; Sealed tube;	30%

phenanthrene (85-01-8) + acetic anhydride (108-24-7) → 1-(phenanthren-3-yl)ethanone (2039-76-1) + 1-Phenanthren-1-yl-ethanone (5968-48-9)

Conditions	Yield
With hydrogen fluoride at 50 - 60℃;

phenanthrene (85-01-8) + acetyl chloride (75-36-5) → 1-(phenanthren-3-yl)ethanone (2039-76-1) + 1-Phenanthren-1-yl-ethanone (5968-48-9)

Conditions	Yield
With aluminium trichloride; nitrobenzene

phenanthrene (85-01-8) + acetyl chloride (75-36-5) → 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
With aluminium trichloride

phenanthrene (85-01-8) + acetyl chloride (75-36-5) → 9-acetylphenanthrene (2039-77-2) + 2-acetylphenanthrene (5960-69-0) + 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
With aluminium trichloride for 30h; Ambient temperature; Further byproducts given;	A 70.6 % Chromat. B 4.0 % Chromat. C 25.0 % Chromat.
With aluminium trichloride Product distribution; Ambient temperature; various time and molar ratio AlCl3/1a;	A 26.5 % Chromat. B 17.1 % Chromat. C 55.1 % Chromat.
With aluminium trichloride for 52h; Ambient temperature;	A 26.5 % Chromat. B 17.1 % Chromat. C 55.1 % Chromat.

phenanthrene (85-01-8) + hydrogen fluoride (7664-39-3) + acetic anhydride (108-24-7) → 2-acetylphenanthrene (5960-69-0) + 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
at 50 - 55℃;

carbon disulfide (75-15-0) + aluminium trichloride (7446-70-0) + phenanthrene (85-01-8) + acetyl chloride (75-36-5) → 2-acetylphenanthrene (5960-69-0) + 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
hoehere Temperaturen;

aluminium trichloride (7446-70-0) + phenanthrene (85-01-8) + nitrobenzene (98-95-3) + acetyl chloride (75-36-5) → 2-acetylphenanthrene (5960-69-0) + 1-(phenanthren-3-yl)ethanone (2039-76-1)

acetophenone (98-86-2) + 4-methyl-2-nitro-benzeneselen(o)ylsulfanyl cyanate → 1-(phenanthren-3-yl)ethanone (2039-76-1) + barium oxide containing copper oxide-chromium oxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 45 percent / H2SO4 / 6.5 h / Ambient temperature 2: 73 percent / 10percent Pd/C / 4.5 h / 300 °C View Scheme

phenanthrene (85-01-8) + acetyl chloride (75-36-5) → 2-acetylphenanthrene (5960-69-0) + 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
With aluminum (III) chloride In nitrobenzene Friedel Crafts acylation;

1-(2-amino-5-bromophenyl)ethanone (29124-56-9) → 1-(phenanthren-3-yl)ethanone (2039-76-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / acetonitrile; water / 4.5 h / 10 - 20 °C / Inert atmosphere; Sealed tube 2: palladium dichloride; 1,3-bis-(diphenylphosphino)propane; potassium carbonate / N,N-dimethyl-formamide / 3 h / 150 °C / Inert atmosphere; Sealed tube View Scheme

1-(phenanthren-3-yl)ethanone (2039-76-1) → 2-bromo-3'-acetophenanthrone (34585-56-3)

Conditions	Yield
With copper(ll) bromide In chloroform; ethyl acetate for 6h; Reflux;	100%
With bromine In 1,4-dioxane; diethyl ether at 20℃; for 3h;	56%
With copper(ll) bromide In chloroform; ethyl acetate for 3.5h; Heating;

1-(phenanthren-3-yl)ethanone (2039-76-1) → phenanthrene-3-carboxylic acid (7470-14-6)

Conditions	Yield
With sodium hydroxide; sodium hypochlorite In 1,4-dioxane at 65℃; for 3h;	100%
With sodium hypochlorite; sodium hydroxide In 1,4-dioxane at 65℃; for 6h;	97%
With sodium hypochlorite solution In 1,4-dioxane; water at 120℃; for 24h;	92%

1-(phenanthren-3-yl)ethanone (2039-76-1) → phenanthren-2-yl-oxoacetaldehyde (1710-28-7)

Conditions	Yield
With selenium (IV) oxide In 1,4-dioxane; water Heating;	99%
With selenium(IV) oxide In toluene
With selenium(IV) oxide

1-(phenanthren-3-yl)ethanone (2039-76-1) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 4-methyl-N′-(1-(phenanthren-3-yl)ethylidene)benzenesulfonohydrazide

Conditions	Yield
In methanol at 60℃;	98%

1-(phenanthren-3-yl)ethanone (2039-76-1) → 1-(3-phenanthryl)ethanol (7494-58-8)

Conditions	Yield
With sodium tetrahydroborate In ethanol for 12h; Ambient temperature;	97%
With ethanol; platinum Hydrogenation;
With copper oxide-chromium oxide; barium(II) oxide; decalin at 100℃; under 97822.5 Torr; Hydrogenation;
With aluminum isopropoxide; isopropyl alcohol
With lithium aluminium tetrahydride; diethyl ether

1-(phenanthren-3-yl)ethanone (2039-76-1) + benzaldehyde (100-52-7) → 1-[3]phenanthryl-3-phenyl-propenone (62953-48-4)

Conditions	Yield
With FeCl3-bentonite for 0.0666667h; Microwave irradiation;	96%
With sodium hydroxide In ethanol for 48h; Ambient temperature;	68.1%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 4-methoxy-benzaldehyde (123-11-5) → C24H18O2

Conditions	Yield
With FeCl3-bentonite for 0.0666667h; Microwave irradiation;	95%

1-(phenanthren-3-yl)ethanone (2039-76-1) + m-tolyl aldehyde (620-23-5) → (Z)-1-Phenanthren-3-yl-3-m-tolyl-propenone (63681-63-0)

Conditions	Yield
With FeCl3-bentonite for 0.0666667h; Microwave irradiation;	95%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 4-nitrobenzaldehdye (555-16-8) → 3-(4-nitro-phenyl)-1-[3]phenanthryl-propenone (31907-28-5)

Conditions	Yield
With FeCl3-bentonite for 0.1h; Microwave irradiation;	94%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 4-bromo-benzaldehyde (1122-91-4) → (E)-3-(4-Bromo-phenyl)-1-phenanthren-3-yl-propenone (38374-12-8)

Conditions	Yield
With FeCl3-bentonite for 0.075h; Microwave irradiation;	93%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 4-methoxy-benzylamine (2393-23-9) → 1-(4-methoxybenzyl)-5-(3-phenanthryl)-1H-1,2,3-triazole

Conditions	Yield
With 4-nitrophenyl azide; acetic acid In toluene at 100℃; for 12h; Molecular sieve;	91%

m-bromobenzoic aldehyde (3132-99-8) + 1-(phenanthren-3-yl)ethanone (2039-76-1) → C23H15BrO

Conditions	Yield
With FeCl3-bentonite for 0.075h; Microwave irradiation;	91%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 2-nitro-benzaldehyde (552-89-6) → (Z)-3-(2-Nitro-phenyl)-1-phenanthren-3-yl-propenone (63646-43-5)

Conditions	Yield
With FeCl3-bentonite for 0.1h; Microwave irradiation;	91%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 2-chloro-benzaldehyde (89-98-5) → (E)-3-(2-Chloro-phenyl)-1-phenanthren-3-yl-propenone (31919-49-0)

Conditions	Yield
With FeCl3-bentonite for 0.0666667h; Microwave irradiation;	90%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 3-Chlorobenzaldehyde (587-04-2) → C23H15ClO

Conditions	Yield
With FeCl3-bentonite for 0.0666667h; Microwave irradiation;	90%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 4-fluorobenzaldehyde (459-57-4) → C23H15FO

Conditions	Yield
With FeCl3-bentonite for 0.0833333h; Microwave irradiation;	90%

1-(phenanthren-3-yl)ethanone (2039-76-1) + 1,5-bis-(morpholino)-pentadienylium triflate → 7-(morpholin-4-yl)-1-(phenanthren-2-yl)hepta-2,4,6-trien-1-one

Conditions	Yield
Stage #1: 1-(phenanthren-3-yl)ethanone With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 1,5-bis-(morpholino)-pentadienylium triflate In tetrahydrofuran; hexane at -78 - 20℃; for 3.25h; Further stages.;	86%

1-(phenanthren-3-yl)ethanone (2039-76-1) → 2-chloro-1-(phenanthren-3-yl)ethanone

Conditions	Yield
With hydrogenchloride; ammonium nitrate; iodine; oxygen In water; acetonitrile at 60℃; for 22h; Green chemistry; chemoselective reaction;	85%

morpholine (110-91-8) + 1-(phenanthren-3-yl)ethanone (2039-76-1) → 3-Phenanthrylacetothiomorpholide (117752-99-5)

Conditions	Yield
With sulfur for 16h; Heating;	82%
With sulfur

1-(phenanthren-3-yl)ethanone (2039-76-1) + methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate (3490-92-4) → 4-methylsulfanyl-2-oxo-6-(phenanthren-3-yl)-2H-pyran-3-carbonitrile (681449-07-0)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 10h;	82%

1-(phenanthren-3-yl)ethanone (2039-76-1) → 3-aminophenanthrene (1892-54-2)

Conditions	Yield
With pyridine; hydroxylamine hydrochloride In ethanol at 75℃; for 1h;	81%
Multi-step reaction with 2 steps 1.1: pyridine; hydroxylamine hydrochloride / ethanol / 3 h / Heating / reflux 2.1: PPA / 2.5 h / 100 °C 2.2: Heating / reflux View Scheme

1-(phenanthren-3-yl)ethanone (2039-76-1) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (S,E)-2-methyl-N-(1-(phenanthren-3-yl)ethylidene)propane-2-sulfinamide

Conditions	Yield
With titanium(IV) tetraethanolate In tetrahydrofuran for 96h; Inert atmosphere; Reflux;	78%

1-(phenanthren-3-yl)ethanone (2039-76-1) → 1-(phenanthren-3-yl)ethanone oxime (5968-50-3)

Conditions	Yield
With pyridine; hydroxylamine hydrochloride In ethanol at 100℃; for 2h; Inert atmosphere;	75.1%
With pyridine; hydroxylamine hydrochloride In ethanol for 3h; Heating / reflux;
With pyridine; hydroxylamine hydrochloride In ethanol for 3h; Heating / reflux;

2-phenyl-indole (948-65-2) + 1-(phenanthren-3-yl)ethanone (2039-76-1) → 6-(phenanthren-3-yl)-11H-benzo[a]carbazole

Conditions	Yield
With iodine(I) bromide In chlorobenzene at 130℃; for 4h; Sealed tube;	75%

1-(phenanthren-3-yl)ethanone (2039-76-1) → 3-(1-chloroethenyl)phenanthrene (228266-66-8)

Conditions	Yield
With phosphorus pentachloride; phosphorus trichloride for 24h; Ambient temperature;	69%

1-(phenanthren-3-yl)ethanone (2039-76-1) + (trifluoromethyl)trimethylsilane (81290-20-2) → 1,1,1-Trifluoro-2-phenanthren-2-yl-propan-2-ol + 1,1,1-Trifluoro-2-phenanthren-3-yl-propan-2-ol

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 2.25h; Ambient temperature; Title compound not separated from byproducts;	A 25% B 66%

1-methyl-2-phenyl-1H-indole (3558-24-5) + 1-(phenanthren-3-yl)ethanone (2039-76-1) → 1-methyl-3-(phenanthro[4,3-b]selenophen-3-yl)-2-phenyl-1H-indole

Conditions	Yield
With selenium; oxygen; iodine(I) bromide In 1-methyl-pyrrolidin-2-one at 140℃; Sealed tube;	63%
With selenium; [bis(acetoxy)iodo]benzene; Iodine monochloride In 1-methyl-pyrrolidin-2-one at 140℃; for 18h;	29%

formaldehyd (50-00-0) + 1-(phenanthren-3-yl)ethanone (2039-76-1) + morpholin hydrochloride (10024-89-2) → 3-morpholino-1-(phenanthren-3-yl)propan-1-one hydrochloride (7470-64-6)

Conditions	Yield
In i-Amyl alcohol Reflux;	60%
Mannich reaction;

1-(phenanthren-3-yl)ethanone (2039-76-1) → (E)-3-Acetylphenanthrene oxime

Conditions	Yield
With hydroxylamine hydrochloride In ethanol Heating;	59%
With pyridine; hydroxylamine hydrochloride In ethanol for 3h; Substitution; Heating;

Upstream product

• 85-01-8 phenanthrene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 7664-39-3 hydrogen fluoride 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 3112-03-6 4-acetylstilbene 
• 1261648-81-0 1-(5-bromo-2-iodophenyl)ethanone 
• 29124-56-9 1-(2-amino-5-bromophenyl)ethanone 
• 98-86-2 acetophenone 

Downstream Products

• 5751-37-1 trans-<3>Phenanthryl-styryl-keton 
• 38374-13-9 2',6'-Dichloro-2-phenanthrylchalcon 
• 50512-27-1 4'-Dimethylamino-3-phenanthrylchalcon 
• 38374-15-1 2',4'-Dihydroxy-2-phenanthrylchalcon 
• 7470-14-6 phenanthrene-3-carboxylic acid 
• 4120-78-9 N-(phenanthren-3-yl)acetamide 
• 144266-80-8 N-Methyl-3-phenanthrenecarboxamide 
• 32155-34-3 phenanthrenequinone-3-carboxylic acid 
• 7470-64-6 3-morpholino-1-(phenanthren-3-yl)propan-1-one hydrochloride 
• 84306-76-3 3-Phenanthrylacetic acid 
• 7470-59-9 3-dimethylamino-1-(phenanthren-3-yl)propan-1-one hydrochloride 
• 7470-69-1 1-(phenanthren-3-yl)-3-piperidinopropan-1-one hydrochloride 
• 31907-28-5 3-(4-nitro-phenyl)-1-[3]phenanthryl-propenone 
• 63646-43-5 (Z)-3-(2-Nitro-phenyl)-1-phenanthren-3-yl-propenone 

Relevant academic research and scientific papers

Air-Driven Potassium Iodide-Mediated Oxidative Photocyclization of Stilbene Derivatives

A new method has been developed for the potassium iodide-mediated oxidative photocyclization of stilbene derivatives. Compared with conventional iodine-mediated oxidative photocyclization reactions, this new method requires shorter reaction times and affords cyclized products in yields of 45-97%. This reaction proceeds with a catalytic amount of potassium iodide and works in an air-driven manner without the addition of an external scavenger. The radical-mediated oxidative photocyclization of stilbene derivatives using TEMPO was also investigated.

Pd-catalyzed tandem homocoupling-aldol-dehydration of ortho-acylphenyl iodides

A Pd-catalyzed cascade Ullmann coupling-aldol-dehydration reaction of ortho-acylphenyl iodides has been explored. This transformation provides a concise access to colchino analogues in moderate to good yields with wide functional group tolerance.

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.

A New and Simple Synthesis of Phenanthrenes

Cyclohexene-1-acetic acid (1) undergoes reaction with various aromatic substrates (2a-k) in the presence of concentrated sulfuric acid to give 1,2,3,4,4a,10a-hexahydro-9-(10H)-phenanthrenones (3a-k) which on dehydrogenation with Pd-C afford the corresponding phenanthrenes (4a-k) in high yields.

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.