505-29-3

Basic information

• Product Name: 1,4-Dithiane
• Synonyms: P-DITHIANE;1,4-Dithiacyclohexane;1,4-Dithiin, tetrahydro-;diethylenedisulfide;para-Dithiane;p-Dithiin, tetrahydro-;FEMA 3831;1,4-DITHIANE
• CAS NO: 505-29-3
• Molecular Formula: C₄H₈S₂
• Molecular Weight: 120.24
• EINECS: 208-007-2
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Alphabetical Listings;C-D;Flavors and Fragrances;Heterocyclic Building Blocks;Others;S-Containing
• Mol File: 505-29-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 107-113 °C(lit.)
• Boiling Point: 200 °C(lit.)
• Flash Point: 82.1 °C
• Appearance: /solid
• Density: 1.062 (estimate)
• Vapor Pressure: 0.459mmHg at 25°C
• Refractive Index: 1.5981 (estimate)
• Storage Temp.: 2-8°C
• Stability: Stable. Incompatible with strong oxidizing agents. Probably combustible.
• CAS DataBase Reference: 1,4-Dithiane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dithiane(505-29-3)
• EPA Substance Registry System: 1,4-Dithiane(505-29-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3335
• WGK Germany: 2
• RTECS: JO5069000
• Hazardous Substances Data: 505-29-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 505-29-3 differently. You can refer to the following data:
1. solid with an extremely unpleasant smell
2. 1,4-Dithiane has a seafood-like odor and a garlic/onion taste.

Uses

1,4-Dithiane has been studied to be used as a way for more efficient rechargeable iron-?air and nickel-?iron batteries through small addition of organo-sulur compounds to metal electrodes.

Definition

ChEBI: A dithiane that is cyclohexane in which the -CH2- units at positions 1 and 2 have been replaced by sulfur atoms.

InChI:InChI=1/C4H8S2/c1-2-6-4-3-5-1/h1-4H2

Synthetic route

ethane-1,2-dithiol (540-63-6) + ethylene dibromide (106-93-4) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With 1-pentyl-3-methylimidazolium bromide at 60℃; for 5.5h;	92%
With sodium ethanolate In ethanol for 2.5h; Cyclization; Heating;	64%

ethane-1,2-dithiol (540-63-6) + 1,2-dichloro-ethane (107-06-2) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With 25percent soude; tetrabutylammomium bromide In benzene at 80℃; for 4h; Product distribution; other concentration of catalyst and soude, time;	87.5%
With 1-pentyl-3-methylimidazolium bromide at 60℃; for 0.133333h; Irradiation; microwave;	81%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 150℃; for 0.333333h; microwave irradiation;	81%

3,6-dithiaoctan-1,8-dithiol (25423-55-6) + 1,2-bis(2-chloroethylthio)ethane (3563-36-8) → 1,4-Dithiane (505-29-3) + 1,4,7,10,13,16-hexathiacyclooctadecan (296-41-3) + 1,4,7,10-tetrathiacyclododecane (25423-56-7)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃;	A n/a B 70% C 5%

2,2,4,4,6,6-hexamethyl-1,3,5,2,4,6-trithiatristanninane (16892-64-1) + ethylene dibromide (106-93-4) → 1,4-Dithiane (505-29-3) + dimethyltin dibromide 1,4-dithiane 2:1 complex + dimethyltin dibromide (2767-47-7)

Conditions	Yield
In further solvent(s) soln. of (Me2SnS)3 in BrCH2CH2Br was heated at 140°C for 35 h; excess C2H4Br2 was removed in vac. at room temp., products were sepd. by sublimation at 70°C; dithiane was identified by chromy., elem. anal. for 2Me2SnBr2*S(CH2CH2)2S;	A n/a B 58% C 18%

{(C5H5)Ru(P(C6H5)3)2(SC2H4)}(1+)*CF3SO3(1-)*0.5CH2Cl2={(C5H5)Ru(P(C6H5)3)2(SC2H4)}(OSO2CF3)*0.5CH2Cl2 (113322-95-5) + tetraphenyl phosphonium chloride (2001-45-8) → 1,4-Dithiane (505-29-3) + chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) (32993-05-8)

Conditions	Yield
In dichloromethane-d2 byproducts: (C2H4S)n; PPh4Cl added to CD2Cl2-soln. of Ru-thiiran complex at 0°C; decompn. by warming to room temp.;	A n/a B 50%

formaldehyd (50-00-0) + ethane-1,2-dithiol (540-63-6) → 1,3-dithiolane (4829-04-3) + 1,4-Dithiane (505-29-3) + 3-methylideneamino-1,5,3-dithiazepane (1449678-80-1) + 1,3,6,8-tetrathiecane (154729-78-9)

Conditions	Yield
With hydrogenchloride; hydrazine hydrate In water at 20℃; pH=0.45 - 0.5;	A 30% B 9% C 49% D 12%

trans-2,3-dichloro-1,4-dithiane (2040-67-7, 89124-15-2) → 1,4-Dithiane (505-29-3) + 2,2'-bi-1,3-dithiolanyl (6784-47-0) + 2,3-dihydro-1,4-dithiin (23230-01-5) + 2,3-dihydro-5,6-dichloro-1,4-dithiin (106691-43-4)

Conditions	Yield
With disodium 1,2-ethanedithiolate In ethanol for 12h;	A 2% B n/a C 15% D 6%

ethylene dibromide (106-93-4) → thirane (420-12-2) + 1,4-Dithiane (505-29-3)

Conditions	Yield
With aluminum oxide; sulfide ion In toluene at 140℃; for 20h;	A 1.5% B 1.8%

thirane (420-12-2) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With aluminum oxide; hydrogen sulfide at 220℃;

2,2'-thiobis-ethanol (111-48-8) → 1,4-Oxathiane (15980-15-1) + 1,4-Dithiane (505-29-3)

Conditions	Yield
With potassium pyrosulfate at 160 - 210℃;
With aluminium silicate at 240℃;
With cation exchanger at 180℃;
With toluene-4-sulfonic acid; acetaldehyde; benzene Unter Entfernen des entstehenden Wassers und Erhitzen des Reaktionsprodukts auf 200grad;
at 180℃; in Gegenwart eines sauren Kationen-Austauschers;

2,2'-thiobis-ethanol (111-48-8) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With aluminum oxide at 225℃;
With hydrogen bromide; phenol

2-(2-benzothiazolylthio)ethanol (4665-63-8) → 1,4-Dithiane (505-29-3) + 2(3H)-Benzothiazolone (934-34-9)

Conditions	Yield
at 125 - 200℃;

1-(2-chloro-ethylsulfanyl)-2-propylsulfanyl-ethane (856365-85-0) → 1,4-Dithiane (505-29-3) + 1-Chloropropane (540-54-5)

Conditions	Yield
beim Erhitzen;

1-butylsulfanyl-2-(2-chloro-ethylsulfanyl)-ethane (159859-35-5) → 1,4-Dithiane (505-29-3) + n-Butyl chloride (109-69-3)

Conditions	Yield
beim Erhitzen;

3,6,9-trithia-1,11-undecanediol (14440-77-8) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With hydrogen bromide; phenol

ethanol (64-17-5) + bis (2-chloroethyl) sulphide (505-60-2) + 3-mercaptopropionitrile (1001-58-7) → 1,4-Dithiane (505-29-3) + 3,3'-thiobis-propanenitrile (111-97-7)

Conditions	Yield
Reagiert des Natriumsalzes;

bis (2-chloroethyl) sulphide (505-60-2) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With sulfur dichloride at 0℃;
With sodium sulfide
With phenol at 180℃; im Rohr;
With sulfur at 200℃;

bis (2-chloroethyl) sulphide (505-60-2) → 1,4-Dithiane (505-29-3) + 1,2-dichloro-ethane (107-06-2)

Conditions	Yield
at 180℃;
at 180℃; Gleichgewicht;

bis (2-chloroethyl) sulphide (505-60-2) → 1,4-Dithiane (505-29-3) + ethene (74-85-1) + 1,2-dichloro-ethane (107-06-2)

Conditions	Yield
at 220℃; Prod.5:HCl;
at 180℃; Prod.5:HCl;

2-(2-mercapto-ethylsulfanyl)-ethanol (98026-19-8) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With hydrogenchloride Erhitzen des Reaktionsprodukts in Phenol bis auf 180grad;

1-Chloro-2-<2-(methylthio)ethylthio>ethane (125787-98-6) → 1,4-Dithiane (505-29-3) + methylene chloride (74-87-3)

Conditions	Yield
beim Erhitzen;

bis(2-hydroxyethyl) disulfide (1892-29-1) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With potassium pyrosulfate under 20 Torr;
With potassium pyrosulfate; phosphoric acid; zinc(II) chloride at 200℃;

2,5,8-trithianonane (37460-04-1) → 1,4-Dithiane (505-29-3) + methylthiol (74-93-1) + 2-methylsulfanyl-ethanethiol (22322-43-6) + methyl vinyl sulfide (1822-74-8)

Conditions	Yield
bei der trockener Destillation;Produkt5:1.2-Bis-<2-methylmercapto-aethylmercapto>-aethan;

1-chloro-3,6-dithiaoctane (92569-22-7) → 1,4-Dithiane (505-29-3) + chloroethane (75-00-3)

Conditions	Yield
Destillation;
beim Erhitzen;

2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol (5244-34-8) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With hydrogen bromide; phenol

2-ethoxy-1,3,2-dithiaphospholane (70164-20-4) + ethyl iodide (75-03-6) → 1,4-Dithiane (505-29-3)

Conditions	Yield
at 90℃;

ethane-1,2-dithiol (540-63-6) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With aluminum oxide at 300℃;

1,2-dichloro-ethane (107-06-2) → 1,4-Dithiane (505-29-3)

Conditions	Yield
With sodium sulfide; ethanol

Dibutyl sulfide (544-40-1) + ethylene dibromide (106-93-4) → 1,4-Dithiane (505-29-3) + 1-bromo-butane (109-65-9)

5,8-dithiadodecane (13362-39-5) + ethylene dibromide (106-93-4) → 1,4-Dithiane (505-29-3)

1,4-Dithiane (505-29-3) + cyclopentadienyldicarbonyl(tetrahydrofuran)iron(II) tetrafluoroborate → {C5H5Fe(CO)2(1,4-dithiane)}BF4

Conditions	Yield
In dichloromethane byproducts: THF; (Ar), organic compound added to soln. of Fe-complex, stirred for 3h (room temp.); filtered, concd. (vacuum), filtered into ether/petroleum ether (2/1), ppt. washed with ether and petroleum ether, dried (vacuum), elem. anal.;	99%

1,4-Dithiane (505-29-3) + cyclopentadienyldicarbonyl(tetrahydrofuran)iron(II) tetrafluoroborate → {(C5H5Fe(CO)2)2(μ-1,4-dithiane)}(BF4)2

Conditions	Yield
In dichloromethane byproducts: THF; (Ar), organic compound added to soln. of Fe-complex (molar ratio: 1/2), stirred for 12h (room temp.); pptd., filtered, washed with ether and petroleum ether, dried (vacuum), elem. anal.;	98%

1,4-Dithiane (505-29-3) + di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium (12092-47-6) + silver(I) hexafluorophosphate (26042-63-7) → [Rh(cyclo-octa-1,5-diene)(dithian)]PF6 (68264-13-1)

Conditions	Yield
In dichloromethane N2-atmosphere; addn. of AgPF6 to suspn. of Rh-complex contg. excess of dithian, stirring for 10 min; filtration, evapn. of filtrate (vac.), crystn. (Me2CO/Et2O); elem. anal.;	98%

1,4-Dithiane (505-29-3) + tris(acetonitrile)pentamethylcyclopentadienylrhodium hexafluorophosphate → [Rh(η5-pentamethylcyclopentadienyl)(acetonitrile)(dithian)](PF6)2

Conditions	Yield
In acetone N2-atmosphere; stirring for 15 min; evapn. (reduced pressure), crystn. (Me2CO/Et2O); elem. anal.;	95%

1,4-Dithiane (505-29-3) + bromoacetic acid (79-08-3) → 1,4-Dithianium-essigsaeure-betain-hydrobromid (30843-64-2)

Conditions	Yield
In nitromethane at 40℃;	93%

1,4-Dithiane (505-29-3) → 1,4-dithiane 1-oxide (19087-70-8)

Conditions	Yield
With nitric acid; Bu4(1+)*AuCl4(1-) In nitromethane; water for 2h; Ambient temperature;	93%
With N-(tert-butyl)-N-chloro-cyanamide In water; acetonitrile at 25℃;	90%
With sodium periodate In water; acetone at 20℃; for 24h;	38.3%

1,4-Dithiane (505-29-3) + silver(I) hexafluorophosphate (26042-63-7) + bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] → [Pd(η3-1-phenylallyl)(dithian)]PF6 (68246-34-4)

Conditions	Yield
In acetone N2-atmosphere; addn. of AgPF6 to suspn. of Pd-complex contg. excess of dithian, stirring for 10 min; filtration, evapn. of filtrate (vac.), crystn. (Me2CO/Et2O); elem. anal.;	92%

1,4-Dithiane (505-29-3) + dimethyltin dichloride (753-73-1) → dimethyltin dichloride 1,4-dithiane 2:1 complex

Conditions	Yield
In neat (no solvent) Me2SnCl2 and 1,4-dithiane were heated at 140°C in a sealed tube under vac. for 12 h; sublimation at 70°C/0.5 mm Hg; elem. anal.;	90%

1,4-Dithiane (505-29-3) + 2CH3(1-)*2Co(3+)*4(HONC(CH3)C(CH3)NO)(1-)=(CH3Co(HONC(CH3)C(CH3)NO)2)2 → CH3Co(HONC(CH3)C(CH3)NO)2(C4H8S2)Co(HONC(CH3)C(CH3)NO)2CH3 (100203-27-8)

Conditions	Yield
In dichloromethane (CH3Co(dmgH)2)2 and dithiane are stirred under N2 in CH2Cl2 at room temp. until all dissolved; ether added, ppt. collected by filtration, washed with ether and dried in vacuo at room temp.; elem. anal.;	90%

1,4-Dithiane (505-29-3) + silver trifluoromethanesulfonate (2923-28-6) → 2Ag(1+)*3(CH2)4S2*2CF3SO3(1-)=[Ag2((CH2)4S2)3][CF3SO3]2

Conditions	Yield
In methanol; dichloromethane addn. of a soln. of 3 equivs. of 1,4-dithiane in CH2Cl2 to a soln. of 2 equivs. of silver salt in methanol, stirring at room temp. for 1 h; filtration, washing with CH2Cl2, drying in vac.; elem. anal.;	90%

1,4-Dithiane (505-29-3) + silver(I) hexafluorophosphate (26042-63-7) + [(norbornadiene)rhodium(I)chloride]2 (12257-42-0) → [Rh(norbornadiene)(dithian)]PF6 (68264-15-3)

Conditions	Yield
In dichloromethane N2-atmosphere; addn. of AgPF6 to suspn. of Rh-complex contg. excess of dithian, stirring for 10 min; filtration, evapn. of filtrate (vac.), crystn. (Me2CO/Et2O); elem. anal.;	90%

1,4-Dithiane (505-29-3) + tert-butyl 4-bromobenzoperoxoate (2123-95-7) → 1,4-dithian-2-yl 4-bromobenzoate

Conditions	Yield
With copper-iron mixed oxide In dichloromethane; acetonitrile at 140℃; for 24h; Sealed tube;	90%

1,4-Dithiane (505-29-3) + tert-butyl 4-methylbenzoperoxoate (22313-60-6) → 1,4-dithian-2-yl 4-methylbenzoate

Conditions	Yield
With copper-iron mixed oxide In dichloromethane; acetonitrile at 140℃; for 24h; Sealed tube;	89%

1,4-Dithiane (505-29-3) + pentacarbonyl(tetrafluoroborato)rhenium (78670-75-4) → {((CO)5Re)(C4H8S2)}(1+)*BF4(1-)={((CO)5Re)(C4H8S2)}BF4 (118504-51-1)

Conditions	Yield
In dichloromethane (Ar); addn. of 1,4-dithiane to a suspn. of one equiv. of (CO)5ReFBF3 and stirring at room temp. for 24 h;; sepn. of the residue; washing with CH2Cl2; vacuum drying; elem. anal.;	87%

1,4-Dithiane (505-29-3) + silver(I) nitrite (7783-99-5) → Ag(1+)*(CH2)4S2*NO2(1-)=[Ag((CH2)4S2)]NO2

Conditions	Yield
In water; acetone addn. of a soln. of 1,4-dithiane in acetone to a soln. of silver salt inwater; elem. anal.;	87%

1,4-Dithiane (505-29-3) + pentacarbonyl(tetrafluoroborato)rhenium (78670-75-4) → {((CO)5Re)2(C4H8S2)}(2+)*2BF4(1-)={((CO)5Re)2(C4H8S2)}(BF4)2

Conditions	Yield
In dichloromethane (Ar); addn. of 1,4-dithiane to a suspn. of two equiv. of (CO)5ReFBF3 and stirring at room temp. for 24 h;; sepn. of the residue; washing with CH2Cl2; vacuum drying; elem. anal.;	85%

1,4-Dithiane (505-29-3) + silver nitrate → AgNO3*{1,4}dithiane (23739-38-0)

Conditions	Yield
In methanol; dichloromethane addn. of a soln. of 1,4-dithiane in CH2Cl2 to a soln. of silver salt in methanol; elem. anal.;	85%
In ethanol
In ethanol

1,4-Dithiane (505-29-3) + mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)] (243643-58-5) → mer-[RuCl3(1,4-bis(diphenylphosphino)butane)(1,4-dithiane)] (890526-28-0)

Conditions	Yield
In dichloromethane all manipulations under Ar atm.; Ru and S compds. dissolved in CH2Cl2 with stirring at room temp. for 12 h; concd.; pptd. with Et2O,filtered, washed with Et2O, dried in vac.; elem.anal.;	85%

1,4-Dithiane (505-29-3) + tert-butyl p-chloroperoxybenzoate (2203-13-6) → 1,4-dithian-2-yl 4-chlorobenzoate

Conditions	Yield
With copper-iron mixed oxide In dichloromethane; acetonitrile at 140℃; for 24h; Sealed tube;	85%

1,4-Dithiane (505-29-3) + [N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ3-bromane (957188-75-9) → C5H8F3NO2S3 (1251955-12-0)

Conditions	Yield
In dichloromethane at -78 - 0℃; for 2h; Inert atmosphere;	84%

1,4-Dithiane (505-29-3) + tert-butyl perester of 4-methoxybenzoic acid (43084-97-5) → 1,4-dithian-2-yl 4-methoxybenzoate

Conditions	Yield
With copper-iron mixed oxide In dichloromethane; acetonitrile at 140℃; for 24h; Sealed tube;	83%

1,4-Dithiane (505-29-3) + palladium(II) hexafluoroacetylacetonate → (C4H8S2)2Pd(2+)*2CF3COCHCOCF3(1-)=(C4H8S2)2Pd(CF3COCHCOCF3)2

Conditions	Yield
In pentane a pentane solution of Pd(F6acac)2 was added to a solution of 1,4-C4H8S2 in pentane with stirring; filtrated and vac. dried;	82%

1,4-Dithiane (505-29-3) + silver(I) hexafluorophosphate (26042-63-7) + (2-methylallyl)palladium-chloride dimer → [Pd(η3-2-methylallyl)(dithian)]PF6 (68246-32-2)

Conditions	Yield
In acetone N2-atmosphere; addn. of AgPF6 to suspn. of Pd-complex contg. excess of dithian, stirring for 10 min; filtration, evapn. of filtrate (vac.), crystn. (Me2CO/Et2O); elem. anal.;	82%

1,4-Dithiane (505-29-3) + RuCl2(1,4-bis(diphenylphosphino)butane)(PPh3) (88496-72-4) → trans-[RuCl2(1,4-bis(diphenylphosphino)butane)(1,4-dithiane)] (890526-27-9)

Conditions	Yield
In dichloromethane all manipulations under Ar atm.; mixt. of Ru and S compds. stirred in CH2Cl2 at room temp. for 30 min; concd.; pptd. with Et2O,filtered, washed with Et2O, dried in vac.; elem.anal.;	80%

1,4-Dithiane (505-29-3) + bis(benzonitrile)palladium(II) dichloride (15617-18-2, 39958-10-6, 14220-64-5) → [PdCl2(dithian)(0.1Me2CO)]n

Conditions	Yield
With acetone In acetone N2-atmosphere; stirring for 16 h (pptn.); filtration, washing (Me2CO, Et2O), drying (vac., 56°C); elem. anal.;	80%

1,4-Dithiane (505-29-3) + potassium hexacyanoruthenate(II) trihydrate → K3[Ru(CN)5(1,4-dithiane)]*3H2O

Conditions	Yield
With bromine In ethanol; water to soln. Ru complex in aq. EtOH Br2 was added and stirred for 20 min, 3-fold excess ligand was added dropwise under Ar and allowed to stand for 1 day; react. mixt. was cooled in ice bath and acetone was added, ppt. was filtered, washed with acetone and Et2O, and dried; elem. anal.;	80%

1,4-Dithiane (505-29-3) + tert-Butyl peroxybenzoate (614-45-9) → 2-(benzoyloxy)-1,4-dithiane (81146-36-3)

Conditions	Yield
With copper-iron mixed oxide In dichloromethane; acetonitrile at 140℃; for 24h; Sealed tube;	80%

1,4-Dithiane (505-29-3) + tetracarbonyldi-μ-chlorodirhodium(I) + silver perchlorate → Rh(1+)*2CO*C4H8S2*[ClO4](1-)=[Rh(CO)2(C4H8S2)][ClO4]

Conditions	Yield
In acetone byproducts: silver chloride; (N2); stoich. amt. of AgClO4 added to complex soln., stirred in dark for 5 min, slight excess of ligand added; filtered (Kieselguhr), collected over Et2O under N2, ppt. filtered off,washed with Et2O, dried in vac.; elem. anal.;	79%

Upstream product

• 64-17-5 ethanol 
• 505-60-2 bis (2-chloroethyl) sulphide 
• 1001-58-7 3-mercaptopropionitrile 
• 1892-29-1 bis(2-hydroxyethyl) disulfide 
• 106-93-4 ethylene dibromide 
• 4755-81-1 methyl 2-chloroacetoacetate 
• 60-24-2 2-hydroxyethanethiol 
• 107-06-2 1,2-dichloro-ethane 
• 7647-01-0 hydrogenchloride 
• 98026-19-8 2-(2-mercapto-ethylsulfanyl)-ethanol 
• 14440-77-8 3,6,9-trithiaundecane-1,11-diol 
• 10035-10-6 hydrogen bromide 
• 108-95-2 phenol 
• 5244-34-8 2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol 

Downstream Products

• 81146-36-3 2-(benzoyloxy)-1,4-dithiane 
• 89124-42-5 1,4-dithiane 1,1,4-trioxide 
• 33976-40-8 1,4-dithiane 1,1,4,4-tetraoxide 
• 57983-04-7 1,4-dithiane 1,4-dioxide 

Relevant articles and documents

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REACTION OF DIHALOALKANES WITH INORGANIC SULFIDES

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Enhanced thermal degradation of 2,2′-dichlorodiethyl sulfide (sulfur mustard, HD) with the presence of metal oxides

Thermal degradation of sulfur mustard (2,2′-dichlorodiethyl sulfide, HD) in the presence of metal oxide adsorbents was investigated by thermal desorption in conjunction with gas chromatography–mass spectrometry (GC-MS). Zr(OH)4, Al2O3, Al2CoO4, MgO, CeO2, and V2O5were used as metal oxide adsorbents. Neat HD was spiked onto the metal oxides packed in glass tubes, which were kept at room temperature and then heated at moderately elevated temperatures of 100°C by a thermal desorption system. The products of thermal degradation were directly transferred and analyzed by GC-MS. 1,4-Dithiane and 1,4-oxathiane were characterized as the major products of the thermal degradation of HD in the presence of Zr(OH)4, Al2O3, Al2CoO4, and CeO2adsorbents. No effective degradation was observed with MgO and V2O5. Of particular note is Zr(OH)4, which extremely enhanced the thermal degradation of HD.

A highly efficient carbon-sulfur bond formation reaction via microwave-assisted nucleophilic substitution of thiols to polychloroalkanes without a transition-metal catalyst

An efficient carbon-sulfur bond formation reaction has been developed under microwave irradiation. This reaction affords a novel and rapid synthesis of thioacetals and sulfides under mild conditions. This method is particularly noteworthy given its experimental simplicity and high generality, and no transition-metal catalysts were needed under our conditions.

Synthetic potentialities of sulfonylsulfonium salts: A new approach to the preparation of disulfonium dications

A new efficient method for the generation of disulfonium dications whose subsequent hydrolysis selectively affords monosulfoxides was developed based on the oxidation of bis-sulfides by trifluoromethanesulfonic anhydride.