77545-45-0

Basic information

• Product Name: 3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide
• Synonyms: 3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide;3',6'-Dichlorospiro[3H-2,1-benzoxathiol-3,9'-[9H]xanthene]-1,1-dioxide
• CAS NO: 77545-45-0
• Molecular Formula: C₁₉H₁₀Cl₂O₄S
• Molecular Weight: 405.2513
• Mol File: 77545-45-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 546.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.67±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide(77545-45-0)
• EPA Substance Registry System: 3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide(77545-45-0)

Safety Data

• Hazardous Substances Data: 77545-45-0(Hazardous Substances Data)

Usage

General Description

3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide is a chemical compound with a complex and unique molecular structure. It contains two chlorine atoms attached to a spiro compound consisting of benzene, oxathiole, and xanthene moieties. The presence of the 1,1-dioxide group adds further complexity to the molecule. 3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide may have potential applications in various fields such as pharmaceuticals, materials science, or organic synthesis due to its intricate structure and functional groups, although further research is necessary to fully understand its properties and potential uses. Additionally, due to its unique molecular structure, it may have specific reactivity and properties that make it of interest to researchers and scientists.

Synthetic route

sulfonefluorescein (4424-03-7) → 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0)

Conditions	Yield
With trichlorophosphate at 105℃; for 18h;	56%
With trichlorophosphate at 90℃; for 2h;	53.4 g
With trichlorophosphate at 90℃; for 2h;	53.4 g

sulfonfluorescein → 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0)

Conditions	Yield
With phosphorus pentachloride at 125 - 130℃;

benzoyl chloride (98-88-4) + sulfonfluorescein → 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0)

Conditions	Yield
at 200℃;

o-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzenesulphonic acid → 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere;
With thionyl chloride

2-sulfobenzoic acid cyclic anhydride (81-08-3) → 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h / 140 °C 2: trichlorophosphate / 2 h / 90 °C View Scheme

recorcinol (108-46-3) → 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h / 140 °C 2: trichlorophosphate / 2 h / 90 °C View Scheme

saccharin (81-07-2) → 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / sulfolane / 20 h / 120 - 140 °C 2: trichlorophosphate / 18 h / 105 °C View Scheme

3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt + C10H15NO2 + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C39H37N2O8S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt; 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 120℃; for 2h; Stage #2: C10H15NO2 In ethylene glycol at 150℃; for 5h;	95%

C12H18N2O + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C43H44N4O6S

Conditions	Yield
With zinc(II) chloride In sulfolane at 180℃; for 6h; Solvent; Temperature;	94%

C11H16NO3S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 2,6-dimethylaniline (87-62-7) → C38H35N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: C11H16NO3S(1-)*Na(1+); 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium triflate In ethylene glycol at 120℃; for 2h; Stage #2: 2,6-dimethylaniline In ethylene glycol at 150℃; for 5h;	94%

3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 2-(2-aminophenyl)propionitrile (88975-17-1) → C37H30N3O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt; 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 120℃; for 2h; Stage #2: 2-(2-aminophenyl)propionitrile In ethylene glycol at 150℃; for 5h;	94%

C10H14NO3S(1-)*Na(1+) (1047719-94-7) + C10H12N2 + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C39H36N3O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: C10H14NO3S(1-)*Na(1+); 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 120℃; for 2h; Stage #2: C10H12N2 In ethylene glycol at 150℃; for 5h;	93%

C10H14NO5S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 2,4,6-trimethylaniline (88-05-1) → C39H37N2O9S2(1-)*Na(1+)

Conditions	Yield
Stage #1: C10H14NO5S(1-)*Na(1+); 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 120℃; for 2h; Stage #2: 2,4,6-trimethylaniline In ethylene glycol at 150℃; for 8h;	92%

C10H14NO5S(1-)*Na(1+) + C13H21NO3 + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C42H43N2O12S2(1-)*Na(1+)

Conditions	Yield
Stage #1: C10H14NO5S(1-)*Na(1+); 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 120℃; for 2h; Stage #2: C13H21NO3 In ethylene glycol at 150℃; for 5h;	92%

3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 2,4,6-trimethylaniline (88-05-1) → C37H33N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt; 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 120℃; for 2h; Stage #2: 2,4,6-trimethylaniline In ethylene glycol at 150℃; for 5h;	92%

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 3,5-dimethylsulphanilic acid, sodium salt → C36H31N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide; 3,5-dimethylsulphanilic acid, sodium salt With magnesium(II) chloride hexahydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethylene glycol at 120℃; Stage #2: 3,5-dimethylsulphanilic acid, sodium salt In ethylene glycol at 150℃; for 8h;	92%

C9H12NO3S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C37H32N2O10S3(2-)*2Na(1+)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 150℃; for 10h;	91%

4-trifluoromethylphenylamine (455-14-1) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 3,5-dimethylsulphanilic acid, sodium salt → C34H24F3N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide; 3,5-dimethylsulphanilic acid, sodium salt With magnesium oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethylene glycol at 120℃; for 2h; Stage #2: 4-trifluoromethylphenylamine In ethylene glycol at 150℃; for 8h;	91%

p-toluidine (106-49-0) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C33H26N2O4S

Conditions	Yield
In ethylene glycol at 120℃; for 18h;	90.96%
In 1-methyl-pyrrolidin-2-one at 120℃; for 6h;

C14H20N2O + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C47H48N4O6S

Conditions	Yield
With zinc(II) chloride In sulfolane at 150℃; for 8h;	90%

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 2,4,6-trimethylaniline (88-05-1) → C37H34N2O4S

Conditions	Yield
With zinc(II) chloride In sulfolane at 200℃; for 3h;	90%
In 1-methyl-pyrrolidin-2-one at 150℃; for 4h;	39%
Stage #1: 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide; 2,4,6-trimethylaniline With zinc(II) chloride In sulfolane at 200℃; for 3h; Stage #2: With hydrogenchloride In water; acetonitrile at 45℃; for 0.5h;	80.4 g
With zinc(II) chloride In sulfolane at 200℃; for 3h;	80 g
With zinc(II) chloride In sulfolane at 200℃; for 3h;	80 g

C10H14NO4S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C39H36N2O12S3(2-)*2Na(1+)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 150℃; for 10h;	90%

3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C37H32N2O10S3(2-)*2Na(1+)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 150℃; for 10h;	90%

3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt + 2-methyl-6-pentafluoroethylaniline (273735-58-3) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C37H28F5N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt; 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 120℃; for 2h; Stage #2: 2-methyl-6-pentafluoroethylaniline In ethylene glycol at 180℃; for 18h;	90%

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 3,5-dimethylsulphanilic acid, sodium salt → C35H28N2O10S3(2-)*2Na(1+)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 150℃; for 10h;	90%

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + diethylamine (109-89-7) → C31H40N3O3S(1+)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 120℃; for 5h;	90%

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + o-toluidine (95-53-4) → C33H26N2O4S

Conditions	Yield
With 1-methyl-2-pyridone at 120℃; for 8h;	89%
In 1-methyl-pyrrolidin-2-one at 150℃; for 4h;	45%

C10H14NO4S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C39H36N2O12S3(2-)*2Na(1+)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In ethylene glycol at 150℃; for 10h;	89%

2,6-diisopropylbenzenamine (24544-04-5) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C43H46N2O4S

Conditions	Yield
With zinc(II) chloride In sulfolane at 200℃; for 4h;	88%
With magnesium chloride In sulfolane at 80 - 125℃; for 53h;	70.8%

2,6-diethyl-4-methylaniline (24544-08-9) + C11H16NO3S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C41H41N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: C11H16NO3S(1-)*Na(1+); 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In ethylene glycol at 120℃; for 2h; Stage #2: 2,6-diethyl-4-methylaniline In ethylene glycol at 180℃; for 18h; Reagent/catalyst;	88%

3-Amino-2,4,6-trimethyl-phenol (114960-27-9) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C37H34N2O6S

Conditions	Yield
With sulfolane; zinc(II) chloride at 200℃; for 6h;	87%

C10H14NO5S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C39H36N2O14S3(2-)*2Na(1+)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In ethylene glycol at 150℃; for 14h;	87%

C11H16NO3S(1-)*Na(1+) + C10H14NO4S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C40H38N2O11S3(2-)*2Na(1+)

Conditions	Yield
Stage #1: C11H16NO3S(1-)*Na(1+); 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In ethylene glycol at 120℃; for 3h; Stage #2: C10H14NO4S(1-)*Na(1+) In ethylene glycol at 180℃; for 18h;	86%

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 2,6-dimethylaniline (87-62-7) → C35H30N2O4S

Conditions	Yield
With 1-methyl-2-pyridone at 150℃; for 8h; Darkness;	85%
With 1-methyl-2-pyridone In 1-methyl-pyrrolidin-2-one at 150℃; for 8h;	85%
With zinc(II) chloride In sulfolane at 200℃; for 4h;	65.6%

2,6-diethyl-4-methylaniline (24544-08-9) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 3,5-diisopropyl sulfanilic acid sodium salt → C42H43N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide; 3,5-diisopropyl sulfanilic acid sodium salt With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In ethylene glycol at 120℃; for 2h; Stage #2: 2,6-diethyl-4-methylaniline In ethylene glycol at 180℃; for 18h;	85%

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + diethylamine (109-89-7) → C27H30N2O4S

Conditions	Yield
In isopropyl alcohol at 80℃; for 8h;	84%
In isopropyl alcohol at 80℃; for 8h;	84%
In isopropyl alcohol at 80℃; for 8h;	84%

3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 3,5-diisopropyl sulfanilic acid sodium salt → C40H38N2O10S3(2-)*2Na(1+)

Conditions	Yield
Stage #1: 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide; 3,5-diisopropyl sulfanilic acid sodium salt With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium chloride In ethylene glycol at 120℃; for 3h; Stage #2: 3-amino-2,4,6-trimethylbenzenesulfonic acid sodium salt In ethylene glycol at 180℃; for 18h;	84%

Upstream product

• 81-08-3 2-sulfobenzoic acid cyclic anhydride 
• 108-46-3 recorcinol 
• 4424-03-7 sulfonefluorescein 
• 81-07-2 saccharin 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1201223-18-8 C₄₁H₃₆N₃O₅S⁽¹⁺⁾ 
• 1412432-09-7 C₄₅H₃₉N₄O₇S⁽¹⁺⁾*C₂F₃O₂^(1-) 
• 1412432-11-1 C₄₁H₃₇N₃O₅S 
• 1412432-08-6 C₃₅H₂₇N₂O₄S⁽¹⁺⁾*Cl^(1-) 

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