86456-22-6

Basic information

• Product Name: 8-{[2-(dimethylamino)ethyl]amino}-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate
• Synonyms: 9H-Xanthen-9-one, 1-((2-(dimethylamino)ethyl)amino)-4-(hydroxymethyl)-7-(((4-methylphenyl)sulfonyl)oxy)-; 9H-Xanthen-9-one, 1-[[2-(dimethylamino)ethyl]amino]-4-(hydroxymethyl)-7-[[(4-methylphenyl)sulfonyl]oxy]-
• CAS NO: 86456-22-6
• Molecular Formula: C₂₅H₂₆N₂O₆S
• Molecular Weight: 482.5487
• Mol File: 86456-22-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 705.7°C at 760 mmHg
• Flash Point: 380.6°C
• Density: 1.364g/cm³
• Vapor Pressure: 6.67E-21mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 8-{[2-(dimethylamino)ethyl]amino}-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 8-{[2-(dimethylamino)ethyl]amino}-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate(86456-22-6)
• EPA Substance Registry System: 8-{[2-(dimethylamino)ethyl]amino}-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate(86456-22-6)

Safety Data

• Hazardous Substances Data: 86456-22-6(Hazardous Substances Data)

Usage

General Description

The chemical "8-{[2-(dimethylamino)ethyl]amino}-5-(hydroxymethyl)-9-oxo-9H-xanthen-2-yl 4-methylbenzenesulfonate" is a complex compound used in the field of chemistry and pharmaceuticals. It is a xanthen compound with a sulfonate group attached to a 4-methylbenzene ring. The compound contains a xanthene core with an aminoethylamine group and a hydroxymethyl group attached to it. The sulfonate group is often used as a counterion in pharmaceutical formulations and has applications in various drug delivery systems. The compound's specific properties and potential uses in different industries still require further research.

Synthetic route

formaldehyd (50-00-0) + 1-<<2-(dimethylamino)ethyl>amino>-7-(toluenesulfonyloxy)-9H-xanthen-9-one (86456-20-4) → NSC 354677 (86456-22-6)

Conditions	Yield
With acetic acid at 70℃; for 72h;	46%

3-iodochlorobenzene (625-99-0) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) K2CO3, 2.) Cu, CuI / 1.) DMF, 120 deg C, 10 min, 2.) DMF, reflux, 50 h 2: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 3: 87 percent / 56percent HI / 4 h / Heating 4: 92 percent / pyridine / 1.5 h / 50 °C 5: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

5-methoxysalicylic acid (2612-02-4) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) K2CO3, 2.) Cu, CuI / 1.) DMF, 120 deg C, 10 min, 2.) DMF, reflux, 50 h 2: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 3: 87 percent / 56percent HI / 4 h / Heating 4: 92 percent / pyridine / 1.5 h / 50 °C 5: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

2-(3-chlorophenoxy)-5-methoxybenzoic acid (86456-12-4) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 2: 87 percent / 56percent HI / 4 h / Heating 3: 92 percent / pyridine / 1.5 h / 50 °C 4: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

1-<<2-(dimethylamino)ethyl>amino>-7-hydroxy-9H-xanthen-9-one (86456-18-0) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / pyridine / 1.5 h / 50 °C 2: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

1-<<2-(dimethylamino)ethyl>amino>-7-methoxy-9H-xanthen-9-one (86456-16-8) → NSC 354677 (86456-22-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / 56percent HI / 4 h / Heating 2: 92 percent / pyridine / 1.5 h / 50 °C 3: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C View Scheme

NSC 354677 (86456-22-6) → 1-[[2-(Dimethylamino)ethyl]amino]-7-hydroxy-4-(hydroxymethyl)-9H-xanthen-9-one (86455-98-3)

Conditions	Yield
With potassium hydroxide In ethanol for 0.5h; Heating;	88%

Upstream product

• 86456-16-8 1-<<2-(dimethylamino)ethyl>amino>-7-methoxy-9H-xanthen-9-one 
• 86456-18-0 1-<<2-(dimethylamino)ethyl>amino>-7-hydroxy-9H-xanthen-9-one 
• 86456-12-4 2-(3-chlorophenoxy)-5-methoxybenzoic acid 
• 2612-02-4 5-methoxysalicylic acid 
• 625-99-0 3-iodochlorobenzene 
• 50-00-0 formaldehyd 
• 86456-20-4 1-<<2-(dimethylamino)ethyl>amino>-7-(toluenesulfonyloxy)-9H-xanthen-9-one 

Downstream Products

• 86455-98-3 1-[[2-(Dimethylamino)ethyl]amino]-7-hydroxy-4-(hydroxymethyl)-9H-xanthen-9-one 

Relevant articles and documents

7-Hydroxylucanthone, 7-hydroxhycanthone and their analogs

7-Hydroxylucanthone and 7-hydroxyhycanthone derivatives have been found to have significant antitumor effect. The derivatives are of the general formula: STR1 wherein the radicals R1 and R2 are lower alkyl groups or other simple groups and R3 is OH where X=O, and H or OH where X=S.