479-50-5

Basic information

• Product Name: lucanthone
• Synonyms: 1-(2-diethylaminoethylamino)-4-(methyl)thioxanthen-9-one;lucanthone;1-[[2-(Diethylamino)ethyl]amino]-4-methyl-9H-thioxanthen-9-one;Lycanthone
• CAS NO: 479-50-5
• Molecular Formula: C₂₀H₂₄N₂OS
• Molecular Weight: 340.48236
• EINECS: 207-532-4
• Mol File: 479-50-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 64.5°C
• Boiling Point: 512.4°C at 760 mmHg
• Flash Point: 263.7°C
• Appearance: /
• Density: 1.0915 (rough estimate)
• Vapor Pressure: 1.3E-10mmHg at 25°C
• Refractive Index: 1.5950 (estimate)
• PKA: 10.00±0.25(Predicted)
• CAS DataBase Reference: lucanthone(CAS DataBase Reference)
• NIST Chemistry Reference: lucanthone(479-50-5)
• EPA Substance Registry System: lucanthone(479-50-5)

Safety Data

• Hazardous Substances Data: 479-50-5(Hazardous Substances Data)

Usage

Safety Profile

Poison by intravenous route. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.

InChI:InChI=1/C20H24N2OS/c1-4-22(5-2)13-12-21-16-11-10-14(3)20-18(16)19(23)15-8-6-7-9-17(15)24-20/h6-11,21H,4-5,12-13H2,1-3H3

Synthetic route

1-amino-4-methyl-thioxanthen-9-one (54236-49-6) + 2-(diethylamino)ethyl chloride (100-35-6) → lucanthone (479-50-5)

Conditions	Yield
at 150℃;

1-amino-4-methyl-thioxanthen-9-one (54236-49-6) + 2-(Diethylamino)ethanol (100-37-8) → lucanthone (479-50-5)

Conditions	Yield
With phosphorus pentoxide at 190℃;

1-chloro-4-methyl-9H-thioxanthen-9-one (57450-55-2) + N,N-diethylethylenediamine (100-36-7) → lucanthone (479-50-5)

Conditions	Yield
With pyridine at 180℃;

1-(2-chloro-ethylamino)-4-methyl-thioxanthen-9-one (19057-92-2) + diethylamine (109-89-7) → lucanthone (479-50-5)

o-Carboxybenzenediazonium (17333-86-7) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: water 2: sulfuric acid 3: pyridine / 180 °C View Scheme

5-chloro-2-methylthiophenol (18858-06-5) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: water 2: sulfuric acid 3: pyridine / 180 °C View Scheme
Multi-step reaction with 3 steps 1: K2CO3; copper-powder; KI / weiteres Reagens: Benzylalkohol 2: sulfuric acid 3: pyridine / 180 °C View Scheme

2-iodo-1-methyl-4-nitrobenzene (7745-92-8) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: copper-powder; xylene 2: aq.-ethanolic NaOH 3: thionyl chloride / anschliesend mit Eisen(III)-chlorid in Benzol erwaermen 4: ethanol; aqueous ammonia; iron (II)-sulfate 5: 150 °C View Scheme
Multi-step reaction with 5 steps 1: copper-powder; xylene 2: aq.-ethanolic NaOH 3: FeSO4 4: polyphosphoric acid / 175 °C 5: 150 °C View Scheme

1-chloro-4-methyl-9H-thioxanthen-9-one (57450-55-2) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; copper-powder / 170 °C 2: phosphoryl chloride View Scheme

5-chloro-2-methyl-benzene-sulfonyl chloride (34981-38-9) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: zinc-powder; aqueous H2SO4 2: water 3: sulfuric acid 4: pyridine / 180 °C View Scheme
Multi-step reaction with 4 steps 1: zinc-powder; aqueous H2SO4 2: K2CO3; copper-powder; KI / weiteres Reagens: Benzylalkohol 3: sulfuric acid 4: pyridine / 180 °C View Scheme

4-methyl-1-nitrothioxanthen-9-one (412339-60-7) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol; aqueous ammonia; iron (II)-sulfate 2: 150 °C View Scheme

1-(2-hydroxy-ethylamino)-4-methyl-thioxanthen-9-one (500360-45-2) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride View Scheme

2-(5-amino-2-methyl-phenylsulfanyl)-benzoic acid (860694-12-8) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: polyphosphoric acid / 175 °C 2: 150 °C View Scheme

2-(5-chloro-2-methyl-phenylsulfanyl)-benzoic acid (408351-36-0) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid 2: pyridine / 180 °C View Scheme

2-(2-methyl-5-nitro-phenylsulfanyl)benzoic acid (412339-71-0) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / anschliesend mit Eisen(III)-chlorid in Benzol erwaermen 2: ethanol; aqueous ammonia; iron (II)-sulfate 3: 150 °C View Scheme
Multi-step reaction with 3 steps 1: FeSO4 2: polyphosphoric acid / 175 °C 3: 150 °C View Scheme

2'-carbomethoxy-2-methyl-5-nitro-diphenyl sulfide (108620-60-6) → lucanthone (479-50-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq.-ethanolic NaOH 2: thionyl chloride / anschliesend mit Eisen(III)-chlorid in Benzol erwaermen 3: ethanol; aqueous ammonia; iron (II)-sulfate 4: 150 °C View Scheme
Multi-step reaction with 4 steps 1: aq.-ethanolic NaOH 2: FeSO4 3: polyphosphoric acid / 175 °C 4: 150 °C View Scheme

lucanthone (479-50-5) → N,N-diethyl-N'-(4-methyl-thioxanthen-1-yl)-ethylenediamine

Conditions	Yield
With ethanol; sodium

lucanthone (479-50-5) → diethyl-methyl-[2-(4-methyl-9-oxo-thioxanthen-1-ylamino)-ethyl]-ammonium; iodide

lucanthone (479-50-5) → triethyl-[2-(4-methyl-9-oxo-thioxanthen-1-ylamino)-ethyl]-ammonium; iodide

Upstream product

• 54236-49-6 1-amino-4-methyl-thioxanthen-9-one 
• 100-35-6 2-(diethylamino)ethyl chloride 
• 100-37-8 2-(Diethylamino)ethanol 
• 57450-55-2 1-chloro-4-methyl-9H-thioxanthen-9-one 
• 100-36-7 N,N-diethylethylenediamine 
• 19057-92-2 1-(2-chloro-ethylamino)-4-methyl-thioxanthen-9-one 
• 109-89-7 diethylamine 
• 17333-86-7 o-Carboxybenzenediazonium 
• 18858-06-5 5-chloro-2-methylthiophenol 
• 7745-92-8 2-iodo-1-methyl-4-nitrobenzene 
• 34981-38-9 5-chloro-2-methyl-benzene-sulfonyl chloride 
• 412339-60-7 4-methyl-1-nitrothioxanthen-9-one 
• 500360-45-2 1-(2-hydroxy-ethylamino)-4-methyl-thioxanthen-9-one 
• 860694-12-8 2-(5-amino-2-methyl-phenylsulfanyl)-benzoic acid