105-65-7

Basic information

• Product Name: Thioperoxydicarbonicacid ([(HO)C(S)]2S2), C,C'-bis(1-methylethyl) ester
• Synonyms: Formicacid, dithiobis[thio-, O,O-diisopropyl ester (6CI,8CI);Thioperoxydicarbonicacid ([(HO)C(S)]2S2), bis(1-methylethyl) ester (9CI);Bis(2-propyl)dixanthogen;Bis(O-isopropylxanthyl) disulfide;Diisopropyltetrathioperoxydicarbonate;Diisopropylxanthogen disulfide;Diproxide;NSC 402565;SanbitDIX
• CAS NO: 105-65-7
• Molecular Formula: C₈H₁₄O₂S₄
• Molecular Weight: 238.3244
• EINECS: 203-319-5
• Mol File: 105-65-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 54-56℃
• Boiling Point: 316.5 °C at 760 mmHg
• Flash Point: 145.2 °C
• Appearance: /
• Density: 1.275 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.509
• Water Solubility: 6.7μg/L at 20℃
• CAS DataBase Reference: Thioperoxydicarbonicacid ([(HO)C(S)]2S2), C,C'-bis(1-methylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: Thioperoxydicarbonicacid ([(HO)C(S)]2S2), C,C'-bis(1-methylethyl) ester(105-65-7)
• EPA Substance Registry System: Thioperoxydicarbonicacid ([(HO)C(S)]2S2), C,C'-bis(1-methylethyl) ester(105-65-7)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R31:; R36/37/38:
• Safety Statements: S26:; S36:
• WGK Germany: 3
• RTECS: XM6844300
• Hazardous Substances Data: 105-65-7(Hazardous Substances Data)

Usage

Hazard

Moderately toxic by ingestion.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H14O4S2/c1-5(2)11-7(9)13-14-8(10)12-6(3)4/h5-6H,1-4H3

Synthetic route

carbon disulfide (75-15-0) + isopropyl alcohol (67-63-0) → diisopropyl xanthogen disulfide (105-65-7)

Conditions	Yield
Stage #1: carbon disulfide; isopropyl alcohol With sodium hydroxide at 35 - 40℃; for 1.16667h; Stage #2: With chlorine for 1.83333h; Time;	95.2%

carbon disulfide (75-15-0) + sodium isopropylate (683-60-3) → diisopropyl xanthogen disulfide (105-65-7)

Conditions	Yield
With carbon tetrabromide at 20℃; for 1h; Cooling with ice;	51%

potassium isopropylxanthate (140-92-1) → diisopropyl xanthogen disulfide (105-65-7)

Conditions	Yield
With iodine; potassium iodide In water for 24h;	40%
With iodine In water; isopropyl alcohol Yield given;
With iron(III) perchlorate In acetonitrile Ambient temperature; determination of amount by potentiometric or spectrophotometric titration;

C15H15NO4S2 (115029-09-9) → 3-phthalimidopropanoic acid (3339-73-9) + diisopropyl xanthogen disulfide (105-65-7) + thioanhydride of phthalylalanine

Conditions	Yield
In benzene for 1h; Irradiation;

alkali salt of/the/ isopropylxanthogenic acid → diisopropyl xanthogen disulfide (105-65-7)

Conditions	Yield
With water; iodine in der Kaelte;
With sodium hypochlorite; water at 15 - 20℃;
With water; chloroamine-T
With bromocyane; water
With sodium hypochlorite; water at 15 - 20℃;

alkali salts of/the/ isopropylxanthogenic acid → diisopropyl xanthogen disulfide (105-65-7)

Conditions	Yield
With chloroform; water; nitrosylchloride

C4H7OS2 → diisopropyl xanthogen disulfide (105-65-7)

Conditions	Yield
In acetonitrile Kinetics; recombination;

sodium isopropylxanthate (140-93-2) → diisopropyl xanthogen disulfide (105-65-7)

Conditions	Yield
With sodium hypochlorite In water; isopropyl alcohol at 0℃; for 0.5h;	81.5 g

bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] + diisopropyl xanthogen disulfide (105-65-7) → [(η5-C5Me5)RuCl2(S2CO(i)Pr)] (918828-87-2)

Conditions	Yield
In acetonitrile (N2); isopropylxanthic disulfide added to a soln. of Ru complex; filtered (silica gel), concd. (vac.), ether added, cooled to -30°C; elem. anal.;	89%

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3) + diisopropyl xanthogen disulfide (105-65-7) → C18H26O10S2

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃;	87%

diisopropyl xanthogen disulfide (105-65-7) + 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (14131-84-1) → O-isopropyl S-(2,3:-4,5-di-O-isopropylidene-α-D-mannofuranos-1-yl) dithiocarbonate

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃; for 5h;	87%

diisopropyl xanthogen disulfide (105-65-7) + 2-(2-methoxyphenyl)-4-chloro-α-azidostyrene → S-((9-chloro-1-methoxyphenanthridin-6-yl)methyl) O-isopropyl carbonodithioate

Conditions	Yield
With dimethyl 2,2'-azobis(isobutyrate) In tetrahydrofuran at 100℃; for 12h; Solvent;	87%

diisopropyl xanthogen disulfide (105-65-7) + 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucopyranose (18464-08-9, 66073-13-0, 71623-44-4, 101981-29-7, 109922-72-7, 109922-73-8, 132287-75-3, 132287-76-4, 132287-78-6, 132303-63-0, 134311-82-3, 134333-39-4) → C30H42O18S2

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃;	86%

diisopropyl xanthogen disulfide (105-65-7) + methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5) → C25H32O6S2

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃;	86%

diisopropyl xanthogen disulfide (105-65-7) + methyl 2,3-di-O-benzyl-β-D-galactopyranoside (6988-40-5, 17791-36-5, 29388-46-3, 31873-34-4, 33164-03-3, 51842-19-4, 52526-60-0, 61117-12-2, 87392-25-4, 117605-35-3) → C25H32O6S2

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃;	83%

(E)-2-penten-4-yn-1-ol (35042-52-5) + diisopropyl xanthogen disulfide (105-65-7) → (E)-4-(3-hydroxyprop-1-enyl)-1,3-dithiol-2-one

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 80℃;	82%
With 2,2'-azobis(isobutyronitrile) In benzene for 20h; Heating;	82%
With 2,2'-azobis(isobutyronitrile) In benzene for 12h; Heating;	82%

diisopropyl xanthogen disulfide (105-65-7) + (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → C20H28O6S2

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃;	82%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4, 6386-24-9, 6564-72-3, 59531-24-7, 69257-52-9, 78184-89-1, 78609-16-2, 78609-17-3, 78609-18-4, 96553-53-6, 104111-61-7, 131347-08-5, 4132-28-9) + diisopropyl xanthogen disulfide (105-65-7) → C38H42O6S2

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃;	82%

diisopropyl xanthogen disulfide (105-65-7) + 2-phenyl-α-azido-styrene → O-isopropyl S-(phenanthridin-6-ylmethyl) carbonodithioate

Conditions	Yield
With dimethyl 2,2'-azobis(isobutyrate) In tetrahydrofuran at 80℃; for 12h; Reagent/catalyst;	82%

diisopropyl xanthogen disulfide (105-65-7) + 2-ethynyl-benzoic acid methyl ester (33577-99-0) → 2-(2-oxo-1,3-dithiol-4-yl)benzoic acid methyl ester

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 80℃;	81%
With 2,2'-azobis(isobutyronitrile) In benzene for 20h; Heating;	81%
With 2,2'-azobis(isobutyronitrile) In benzene for 12h; Heating;	81%

diisopropyl xanthogen disulfide (105-65-7) + phenylacetylene (536-74-3) → 4-phenyl-1,3-dithiol-2-one (939-11-7)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 80℃;	80%

C13H20O6 + diisopropyl xanthogen disulfide (105-65-7) → C17H26O6S2

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃;	80%

bis(cyclopentadienylchromium tricarbonyl) + diisopropyl xanthogen disulfide (105-65-7) → [(η5-C5H5)Cr(CO)2(η2-S2COCH(CH3)2)] (853731-99-4)

Conditions	Yield
In toluene (N2 or Ar); stirring a mixt. of chromium complex and ligand in toluene at room temp. for 2 h; concn., addn. of n-hexane, cooling overnight at -30°C; elem. anal.;	80%

diisopropyl xanthogen disulfide (105-65-7) + 1-ethynyl-3-methoxybenzene (768-70-7) → 4-(3-methoxyphenyl)-1,3-dithiol-2-one

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 80℃;	78%
With 2,2'-azobis(isobutyronitrile) In benzene for 20h; Heating;	78%

diisopropyl xanthogen disulfide (105-65-7) + 2-ethynylquinoxaline (98813-70-8) → 4-(Quinoxalin-2-yl)-1,3-dithiol-2-one (117927-03-4)

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) In toluene for 7h; Heating;	77%

3-ethynylquinoline (78593-40-5) + diisopropyl xanthogen disulfide (105-65-7) → 4-(3-quinolinyl)-1,3-dithiol-2-one

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene for 18h; Heating;	77%

diisopropyl xanthogen disulfide (105-65-7) + 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-(quinoxalin-2-yl)ethyne → 4-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(quinoxalin-2-yl)-1,3-dithiol-2-one (418764-59-7)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene for 3h; Heating;	77%

diisopropyl xanthogen disulfide (105-65-7) + 1,2-O-isopropylidene-α-D-xylose (20031-21-4) → C12H20O5S2

Conditions	Yield
With tributylphosphine; 4 A molecular sieve In toluene at 20℃;	77%

1-ethenylcyclohexene (931-49-7) + diisopropyl xanthogen disulfide (105-65-7) → 4-(cyclohex-1-enyl)-1,3-dithiol-2-one

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene at 80℃;	76%
With 2,2'-azobis(isobutyronitrile) In benzene for 20h; Heating;	76%
With 2,2'-azobis(isobutyronitrile) In benzene for 10h; Heating;	76%

diisopropyl xanthogen disulfide (105-65-7) + 4-ethynylbenzoic acid methyl ester (3034-86-4) → 4-(2-oxo-1,3-dithiol-4-yl)benzoic acid methyl ester

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene for 12h; Heating;	76%

1-Phenylprop-1-yne (673-32-5) + diisopropyl xanthogen disulfide (105-65-7) → 4-methyl-5-phenyl-2-oxo-1,3-dithiole (49675-89-0)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene for 17h; Heating;	75%

norborn-2-ene (498-66-8) + diisopropyl xanthogen disulfide (105-65-7) → exo-3,5-dithia-4-oxotricyclo<5.2.1.02,6>decane (125226-02-0)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene for 15h; Heating;	74%

diisopropyl xanthogen disulfide (105-65-7) + (4-ethynylphenyl)methanol (10602-04-7) → 4-(4-hydroxymethylphenyl)-1,3-dithiol-2-one

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene for 15h; Heating;	74%

diisopropyl xanthogen disulfide (105-65-7) + 2-(1-azidovinyl)-4'-chloro-1,1'-biphenyl → S-((3-chlorophenanthridin-6-yl)methyl) O-isopropyl carbonodithioate

Conditions	Yield
With dimethyl 2,2'-azobis(isobutyrate) In acetonitrile at 100℃; for 12h; Temperature; Solvent;	74%

diisopropyl xanthogen disulfide (105-65-7) + 2-(2-methoxyphenyl)-α-azidostyrene → O-isopropyl S-((1-methoxyphenanthridin-6-yl)methyl) carbonodithioate

Conditions	Yield
With dimethyl 2,2'-azobis(isobutyrate) In tetrahydrofuran at 80℃; for 12h; Reagent/catalyst;	72%

5-(1-methylindolyl)acetylene (61640-21-9) + diisopropyl xanthogen disulfide (105-65-7) → 4-(1-methyl-1H-indol-5-yl)-[1,3]dithiol-2-one (1338778-09-8)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In benzene for 24h; Inert atmosphere; Reflux;	68%
With 2,2'-azobis(isobutyronitrile) In benzene for 24h; Reflux; Inert atmosphere;	68%

3,9-bis(acetoxy)-1,11-bis(quinoxalin-2-yl)undeca-1,10-diyne (871036-27-0) + diisopropyl xanthogen disulfide (105-65-7) → 1,7-bis(acetoxy)-1,7-bis(4-(quinoxalin-2-yl)-1,3-dithiol-2-on-5-yl)heptane

Conditions	Yield
With 1,1'-azobis(1-cyanocyclohexanenitrile) In toluene for 2h; Heating;	62%

Upstream product

• 140-92-1 potassium isopropylxanthate 
• 140-93-2 sodium isopropylxanthate 
• 75-15-0 carbon disulfide 
• 67-63-0 isopropyl alcohol 
• 683-60-3 sodium isopropylate 
• 115029-09-9 C₁₅H₁₅NO₄S₂ 

Downstream Products

• 26564-33-0 Diphenylmethylen-bis-isopropylxanthogenat 
• 19615-06-6 Diisopropyldithiocarbonat 
• 141-98-0 O-isopropyl-N-ethylthionocarbamate 
• 1342805-69-9 methyl 4-(2-oxo-5-phenyl-1,3-dithiol-4-yl)benzoate 
• 1022217-11-3 (1S,2R)-O-isopropyl-S-(2-hydroxycyclohexyl)dithiocarbonate 
• 42574-02-7 4,5-diphenyl-1,3-dithio-4-cyclopenten-2-one 
• 49675-89-0 4-methyl-5-phenyl-2-oxo-1,3-dithiole 
• 939-11-7 4-phenyl-1,3-dithiol-2-one 

Relevant articles and documents

Redox-active proligands from the direct connection of 1,3-dithiol-2-one to tetrathiafulvalene (TTF): Syntheses, characterizations and metal complexation

In the search for novel tetrathiafulvalene-substituted dithiolene ligands, two tetrathiafulvalene (TTF) molecules directly connected to 1,3-dithiol-2-one fragments have been synthesized and characterized by single crystal X-ray diffraction, electrochemical and spectroscopic analyses. TTF1 was obtained, in moderate yield, by the cross-coupling of 4,5-bis(methylthio)-1,3-dithiole-2-one with 4,4′-bis(1,3-dithiole-2-one) in triethylphosphite, whereas for TTF2, the 1,3-dithiol-2-one fragment was introduced, in high yield, by an original reaction of the alkyne group of an ethynyl TTF (Me3TTF-CCH) with xanthogen in the presence of a radical initiator. Opening of the 1,3-dithiol-2-one fragments with sodium methanolate leads to the formation of two new 1,2-dithiolate ligands functionalized with redox-active TTF moieties, which can efficiently coordinate metals. As an illustration, two original heteroleptic bis(cyclopentadienyl)dithiolene titanium complexes were isolated and characterized.

A two-trisulfide isopropyl xanthate preparation method (by machine translation)

The present invention discloses a two-trisulfide isopropyl xanthate preparation method, in order to isopropanol, solid alkali, carbon bisulfide and chlorine as raw materials, the materials are added into the reactor, and then each raw material in shear dispersion under reaction, make the disulfide isopropyl xanthate. The invention oxidant chlorine, thereby avoiding the introduction of water, meets the isopropyl alcohol with carbon disulfide reaction needs anhydrous conditions, will be isopropyl xanthate and oxidation of the generation of the two-step reaction "combined", the "one-step" process for preparing disulfide isopropyl xanthate. At the same time, through the isopropanol is used as the dispersion medium, controls the oxidant chlorine access time, access time and other reaction conditions, the product of the invention yield and purity are higher, with the use of sodium hypochlorite as oxidizing agent compared with the "two-step" process, simplifying the process, the amount of raw material is reduced, thereby reducing the waste of the emissions, ensuring the product yield. (by machine translation)

Photochemical and Thermal Transformations of O-Alkyl-S-phthalylalanyl Xanthates

The reaction of phthalylalanyl chloride with different potassium O-alkylxanthates (R = Et, n-pr, iso-pr, n-Bu, iso-Bu) around 0 deg C in ether solution gave rise to the corresponding O-alkyl-S-phthalylalanyl xanthates.Irradiation of the latter in benzene solution gave xanthic acid disulphide, phthalylalanine and thioanhydride of phthalylalanine in addition to some other products.Thermal decomposition of these acylxanthates around 150 - 60 deg C for 15 - 20 min yielded the corresponding esters and carbon disulphide.