2039-76-1

Basic information

• Product Name: 3-ACETYLPHENANTHRENE
• Synonyms: 1-phenanthren-3-ylethanone;3-Acetylphenanthrene technical grade, 90%;3-ACETYLPHENANTHRENE;1-(3-Phenanthryl)ethanone;Ethanone, 1-(3-phenanthrenyl)-;Ketone, methyl 3-phenanthryl;methyl 3-phenanthryl ketone;3-ACETYLPHENANTHRENE, TECH., 90%
• CAS NO: 2039-76-1
• Molecular Formula: C₁₆H₁₂O
• Molecular Weight: 220.27
• EINECS: 218-020-5
• Product Categories: C15 to C38;Carbonyl Compounds;Ketones;API intermediates
• Mol File: 2039-76-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 67-71 °C(lit.)
• Boiling Point: 405.9 °C at 760 mmHg
• Flash Point: 180.7 °C
• Appearance: White to pale yellow/Powder
• Density: 1.164 g/cm³
• Vapor Pressure: 8.47E-07mmHg at 25°C
• Refractive Index: 1.685
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3-ACETYLPHENANTHRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETYLPHENANTHRENE(2039-76-1)
• EPA Substance Registry System: 3-ACETYLPHENANTHRENE(2039-76-1)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 2039-76-1(Hazardous Substances Data)

Usage

Uses

3-?Acetylphenanthrene is a derivative of Phenanthrene (P294800), which is a polyaromatic hydrocarbon, often viewed as a environmental pollutant.

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

• 38374-11-7 2'-Brom-2-phenanthrylchalcon 
• 32155-34-3 phenanthrenequinone-3-carboxylic acid 
• 31907-28-5 3-(4-nitro-phenyl)-1-[3]phenanthryl-propenone 
• 63646-43-5 (Z)-3-(2-Nitro-phenyl)-1-phenanthren-3-yl-propenone 
• 63681-63-0 (Z)-1-Phenanthren-3-yl-3-m-tolyl-propenone 
• 31919-49-0 (E)-3-(2-Chloro-phenyl)-1-phenanthren-3-yl-propenone 
• 38374-12-8 (E)-3-(4-Bromo-phenyl)-1-phenanthren-3-yl-propenone 
• 56961-99-0 3-chlorophenanthrene-9,10-dione 
• 1892-54-2 3-aminophenanthrene 

Relevant articles and documents

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.

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.