10215-25-5

Basic information

• Product Name: 3,6-THIOXANTHENEDIAMINE-10,10-DIOXIDE
• Synonyms: 3,7-THIAXANTHENEDIAMINE-5,5-DIOXIDE;3,6-THIOXANTHENEDIAMINE-10,10-DIOXIDE;9h-thioxanthene-3,6-diamine,10,10-dioxide;9h-thioxanthene-3,7-diamine,5,5-dioxide;3,6-Diamino-9H-thioxanthene 10,10-dioxide;3,6-Thioxanthenediamine-10,10-dioxide,97%;3,6-ThioxanthenediaMine-10,10-dioxide, 97% 25GR;3,6-DiaMinothioxanthene 10,10-Dioxide
• CAS NO: 10215-25-5
• Molecular Formula: C₁₃H₁₂N₂O₂S
• Molecular Weight: 260.31
• EINECS: 233-527-1
• Product Categories: Aromatics Compounds;Aromatics
• Mol File: 10215-25-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 213-215 °C
• Boiling Point: 570.3°Cat760mmHg
• Flash Point: 298.7°C
• Appearance: Beige to yellow-green/Powder
• Density: 1.2693 (rough estimate)
• Vapor Pressure: 5.09E-13mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly, Heated)
• PKA: 3.62±0.20(Predicted)
• Stability: Store under Argon
• CAS DataBase Reference: 3,6-THIOXANTHENEDIAMINE-10,10-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-THIOXANTHENEDIAMINE-10,10-DIOXIDE(10215-25-5)
• EPA Substance Registry System: 3,6-THIOXANTHENEDIAMINE-10,10-DIOXIDE(10215-25-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 10215-25-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow-Green Crystals

Uses

3,6-Thioxanthenediamine-10,10-dioxide (cas# 10215-25-5) is a compound useful in organic synthesis.

InChI:InChI=1/C13H12N2O2S/c14-10-3-1-8-5-9-2-4-11(15)7-13(9)18(16,17)12(8)6-10/h1-4,6-7H,5,14-15H2

Synthetic route

4,4'-diamino diphenyl methane (101-77-9) → 3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5)

Conditions	Yield
With fuming sulfuric acid at 80℃; for 17h;	83%
With sulfuric acid

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) + allyl bromide (106-95-6) → C25H28N2O2S

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	81%

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) + N-Cyanoguanidine (127099-85-8, 780722-26-1) + acetone (67-64-1) → C23H28N10O2S*2ClH (96615-92-8)

Conditions	Yield
With hydrogenchloride In methanol for 16.8h; Heating;	28%

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) → 3,6-diaminoxanthone

Conditions	Yield
With sodium persulfate In water; N,N-dimethyl-formamide at 80℃; for 9h; Reagent/catalyst;	4%

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) → sulfone pyronin + sulfone

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium persulfate / water; N,N-dimethyl-formamide / 9 h / 80 °C 2: sodium tetrahydroborate / tetrahydrofuran / 72 h / 4 - 40 °C View Scheme

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) → sulfone

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium persulfate / water; N,N-dimethyl-formamide / 9 h / 80 °C 2: sodium tetrahydroborate / tetrahydrofuran / 72 h / 4 - 40 °C 3: acetonitrile; water View Scheme

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) → C25H26N2O3S

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 80 °C 2: chloranil / 1,2-dichloro-ethane / Reflux View Scheme

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) → C32H33N2O2S(1+)*C2F3O2(1-)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 80 °C 2.1: chloranil / 1,2-dichloro-ethane / Reflux 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere 4.1: dichloromethane / 0.5 h / 20 °C View Scheme

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) → C32H34N2O2S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 80 °C 2.1: chloranil / 1,2-dichloro-ethane / Reflux 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere View Scheme

3,6-diamino-thioxanthene-10,10-dioxide (10215-25-5) → sulfone rosamine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 80 °C 2.1: chloranil / 1,2-dichloro-ethane / Reflux 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere 4.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / 5 h / 20 °C View Scheme

Upstream product

• 101-77-9 4,4'-diamino diphenyl methane 

Relevant articles and documents

Synthesis, stability and spectral behavior of fluorogenic sulfone-pyronin and sulfone-rosamine dyes

The first synthesis of sulfone-pyronin and sulfone-rosamine dyes bearing optically tunable primary amino groups (acting as fluorogenic centers) is presented. Sulfone analogs of xanthene-based fluorophores have recently been highlighted as a new class of near-infrared (NIR) fluorescent dyes (Liu et al. ACS Appl Mater Interfaces 2016; 8(35):22953-62), and the availability of fluorogenic derivatives is essential for the rapid construction of “turn-on” reactive probes for chemoselective bioimaging. However, these fluorescent anilines have been found to be unstable in aqueous physiological conditions due to the marked electrophilicity of their meso-position and hence its propensity to undergo nucleophilic attack by a water molecule or a hydroxyde anion. Further investigations have helped us to determine the acidic pH range at which the sulfone-rosamine 2 is fully-stable and a complete assessment of the photophysical properties could be performed. Its pro-fluorescent character and utility were then proved by the preparation and in vitro enzymatic activation of a penicillin G acylase (PGA) sensitive fluorogenic probe.