Category: 1002-41-1

Sachin, L. Sai published the artcileMass spectral studies on vinylic degradation products of sulfur mustards under gas chromatography/mass spectrometry conditions, Synthetic Route of 1002-41-1, the publication is European Journal of Mass Spectrometry (2015), 21(6), 791-800, database is CAplus and MEDLINE.

Sulfur mustards are a class of vesicant chem. warfare agents that rapidly degrade in environmental samples. The most feasible degradation products of sulfur mustards are chloroethyl vinylic compounds and divinylic compounds, which are formed by the elimination of one and two HCl mols. from sulfur mustards, resp. The detection and characterization of these degradation products in environmental samples are an important proof for the verification of sulfur mustard usage. In this study, we synthesized a set of sulfur mustard degradation products, i.e., divinylic compounds (1-7) and chloroethyl vinylic compounds (8-14), and characterized using gas chromatog./mass spectrometry (GC/MS) under electron ionization (EI) and chem. ionization (CI) (methane) conditions. The EI mass spectra of the studied compounds mainly included the fragment ions that resulted from homolytic cleavages with or without hydrogen migrations. The divinylic compounds (1-7) showed [M-SH]+ ions, whereas the chloroethylvinyl compounds (8-14) showed [M-Cl]+ and [M-CH2CH2Cl]+ ions. Methane/CI mass spectra showed [M+H]+ ions and provided mol. weight information. The GC retention index (RI) values were also calculated for the studied compounds The EI and CI mass spectral data together with RI values are extremely useful for off-site anal. for the verification of the chem. weapons convention and also to participate in official Organization for the Prohibition of Chem. Weapons proficiency tests.

European Journal of Mass Spectrometry published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, Synthetic Route of 1002-41-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wils, E. R. J. published the artcileDetermination of mustard gas and related vesicants in rubber and paint by gas chromatography-mass spectrometry, Recommanded Product: 1,2-Bis(2-chloroethyl)disulfane, the publication is Journal of Chromatography (1992), 625(2), 382-6, database is CAplus.

The determination of mustard gas (2,2′-dichlorodiethyl sulfide) and some related vesicants in rubber and paint was investigated. The vesicants were isolated by extraction with CH₂Cl₂ or by dynamic headspace anal. at elevated temperatures The latter procedure had the advantage that high-boiling additives did not interfere during the anal. by capillary column gas chromatog.-mass spectrometry. The stability of the vesicants in the materials used proved to be good. No great losses were found after storage for weeks at room temperature

Journal of Chromatography published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C9H12O, Recommanded Product: 1,2-Bis(2-chloroethyl)disulfane.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Wilson, G. Edwin Jr. published the artcileHalosulfonium salts. IX. Halogen-induced ring cleavages of 1,3-oxathiolanes, Formula: C4H8Cl2S2, the publication is Journal of Organic Chemistry (1976), 41(6), 966-8, database is CAplus.

Halogenation of the 2,2-disubstituted 1,3-oxathiolanes derived from benzophenone, diisopropyl ketone, and cycloheptanone provides a route to regenerate the ketone in good yield. For diisopropyl ketone addnl. products, Me2CHCOCMe2S(CH2)2R (R = Cl, Br), are obtained.

Journal of Organic Chemistry published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C7H7BF2O3, Formula: C4H8Cl2S2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Hemstroem, P. published the artcileIdentification and toxicological evaluation of cyclic sulfonium ion degradation products of sulphur mustard, Recommanded Product: 1,2-Bis(2-chloroethyl)disulfane, the publication is Marine Environmental Research (2020), 105047, database is CAplus and MEDLINE.

In the aftermath of WWII large amount seized German chem. munitions were dumped in the Baltic Sea by Allied forces. In this work, we have compared the chem. content of the solidified blocks of dumped WWII mustard gas collected from the Baltic Sea with solid precipitate from stored mustard gas, known as heel. We have identified the same cyclic sulfonium ions in both samples. In assessing the environmental and toxicol. impact of dumped sulfur mustard munitions on the worlds oceans the potential risk posed by cyclic sulfur mustard salts have so far not been incorporated. The toxicity of 1-(2-chloroethyl)-1,4-dithiane and its hydrolysis product 1-(2-hydroxyethyl)- 1,4-dithiane was evaluated using three different cell lines. Their effect on released pro-inflammatory cytokines was also measured. The toxicity tests showed low toxicity and low pro-inflammatory response and we therefore conclude that the environmental threat posed by these compounds is low.

Marine Environmental Research published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, Recommanded Product: 1,2-Bis(2-chloroethyl)disulfane.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Haszeldine, Robert N. published the artcilePerfluoroalkyl derivatives of sulfur. Part XIX. Reaction of fluoroolefins with fluoride ion in the presence of dimethyl disulfide, and related reactions, Category: chlorides-buliding-blocks, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1976), 1178-82, database is CAplus.

F2C:CF2 reacted with CsF in the presence of MeS2Me to give 15% CF3CFRSMe (I; R = F), 77% MeSCF2CFRSMe (II; R = F), and 2% CF3CF2H, whereas F2C:CFCl gave 15% I (R = Cl), 56% II (R = Cl) and 13% of a mixture (III) of cis- and trans-MeSCF:CFR (R = Cl. Under similar conditions CF3CF:CF2 gave 38% I (R = CF3) and 12-21% III (R = CF3) together with olefin telomers. F2C:CF2 with CsF in the presence of Me2S gave only CF3CF2H. F2C:CFCl and CF3CF:CF2 reacted with NaSMe in Et2O at -196° to give 77 and 90% III, resp.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, Category: chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Kinnear, A. M. published the artcileComposition of mustard gas made by the Levinstein process, HPLC of Formula: 1002-41-1, the publication is Journal of the Society of Chemical Industry, London, Transactions and Communications (1948), 107-10, database is CAplus.

cf. Fuson, et al., C.A. 41, 689g. A sample of Levinstein mustard gas was found to contain 61.4% S(CH₂CH₂Cl)₂ (I), m. 14.45°; 4.3% S₂(CH₂CH₂Cl)₂ (II), colorless liquid, m. 0.2°, b_0.3 90-2°; 17.4% S₃(CH₂CH₂Cl)₂ (III), m. 27°, b_0.3 110-12°; 10.7% S (free and combined with III); 6.2% tars and exptl. losses. I, II, and III were synthesized as follows: HOCH₂CH₂Cl and Na₂S₄ gave S(C₂H₄OH)₂, S₂(C₂H₄OH)₂, and S₃(C₂H₄OH)₂. These products and HCl gave I, II, and III, resp. On boiling with NaI in MeOH, II gave S₂(CH₂CH₂I)₂, m. 42°. II and PhONa in alc. gave S₂(CH₂CH₂OPh)₂, m. 96°. The labile polysulfide (IV) (S combined with III), upon boiling in Me₂CO formed S and III. IV was synthesized by heating 1 g. mol. III with 3 g. atoms rhombic S at 110° for several hrs. Since I or II do not form polysulfides on heating with S, it is thought that IV has a structure of the type (ClCH₂CH₂S)₂S→S→Sâ†?or(ClCH₂CH₂S)₂Sâ†?sub>S→Sâ†?/sub>→S→Sâ†?

Journal of the Society of Chemical Industry, London, Transactions and Communications published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, HPLC of Formula: 1002-41-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Kozlov, S. A. published the artcileEstablishment of reasons for the formation of chloric-organic compounds in commodity oil, Synthetic Route of 1002-41-1, the publication is Neftepromyslovoe Delo (2019), 64-69, database is CAplus.

At present, normative documents set strict requirements to the amount of light organic-chloric compounds (LOHC) in oil intended for delivery to pipeline transportation system. LOHC high concentrations in oil and oil fractions increase the intensity of corrosion and the sedimentation amount inside the technol. equipment, on the equipment surface as well deactivation of the catalytic compositions during oil refining processes. That’s why, with account of the above-said, the problems of LOHC amount control in oil and fixing the reasons for their occurrence are very urgent oil production and oil processing enterprises. The paper analyzes the possible reasons for registering LOHC increased amounts The determination of LOHC in oils and acidic compounds, which are used to enhance oil production is exptl. studied, LOHC possible formation during oil and hydrochloric acid interaction, including in reservoir conditions, is evaluated. The results of exptl. studies have shown that acidic compositions can contain organic-chloric compounds (OCC). It has been established that oil treatment by hydrochloric acid under reservoir conditions provides formation of an addnl. organic-chloric compounds, and LOHC content increases depending on the temperature raise in the reservoir during treatment. The increase of the organic-chloric components concentration in oil also depends on the type of the rock. The use of disintegrated carbonate core, under other equal conditions, compared with the terrigenous rock, leads to a more significant increase in the organic-chloric compounds concentration in oil.

Neftepromyslovoe Delo published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, Synthetic Route of 1002-41-1.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Saeidian, Hamid published the artcileHarmony of computational quantum chemistry and experimental chemistry: Comprehensive DFT studies, microsynthesis, and characterization of mustard gas polysulfide analogues, COA of Formula: C4H8Cl2S2, the publication is Journal of Molecular Structure (2018), 57-62, database is CAplus.

After microsynthesis, structures of mustard gas polysulfide analogs were characterized using electron impact (EI) mass spectrometry. General EI fragmentation pathways for such compounds are proposed. The structure of sulfur mustard (HD) and its two other polysulfide analogs have been examined through B3LYP/6-311++G(2d, 2p) calculations Geometrical anal. of HD shows that the calculated bond distances are satisfactorily comparable with exptl. results. Calculated NMR chem. shifts for HD also were compared with exptl. data, indicating good agreement both for ¹H and ¹³C atoms. The vibrational frequencies of HD and polysulfide analogs have been precisely assigned. At the end, based on visual inspection of lowest unoccupied MOs and the relative difference in the total energies of their episulfonium ions, relative reactivity of HD and its polysulfide analogs were investigated.

Journal of Molecular Structure published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, COA of Formula: C4H8Cl2S2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Donovan, William H. published the artcileUsing theoretical descriptions in structure activity relationships: retention indexes of sulfur vesicants and related compounds, Name: 1,2-Bis(2-chloroethyl)disulfane, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1996), 83-9, database is CAplus.

The authors have conducted a theor. linear solvation energy relation (TLSER) investigation of gas chromatog. (GC) retention indexes for a series of 37 organosulfur compounds on three different columns, deriving regression equations based on descriptors obtained using the MNDO, AM1 and PM3 Hamiltonians. In all cases, satisfactory regressions based on two or three descriptors results, with mol. volume being the most important descriptor. The results are qual. similar to those of Woloszyn and Jurs who, considering the same sulfur vesicant GC retention data set, applied an objective feature selection procedure to winnow descriptors from an initial set of 100, but were not able to treat any compounds containing sulfur-sulfur bonds. The approach was free of this restriction, allowing for consideration of all 37 compounds Only relatively small differences were obtained in the statistical quality of the regressions derived from the three Hamiltonians considered, and among the three GC columns.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, Name: 1,2-Bis(2-chloroethyl)disulfane.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Brintzinger, Herbert published the artcileOrganic sulfur chlorides. VII. Syntheses with α-chloroethylsulfur chloride, Product Details of C4H8Cl2S2, the publication is Chemische Berichte (1954), 300-14, database is CAplus.

cf. C.A. 47, 7433a. Adding 68 g. SO₂Cl₂ dropwise at -20° to 61.5 g. (EtS)₂ in 150 cc. CCl₄, adding another 123 g. SO₂Cl₂ at -15°, warming the mixture to 20°, keeping it overnight, and distilling it give 90% MeCHClSCl (I), b₂₇ 38°. Passing CHCH into 13.1 g. I in 50 cc. CCl₄ 3 h. and distilling the mixture give CHCl:CHSCHClMe, b₁₄ 75°, which decompose on standing. Adding dropwise 10.5 g. cyclohexene in 40 cc. CCl₄ to 13.5 g. I at 20° gives α-chloroethyl 2-chlorocyclohexyl sulfide (II) which decompose on distillation at 2 mm. Heating II at 150° until HCl is no longer split off and distilling off the volatile part leave a thermoplastic dark brown resin. Adding 6.6 g. cyclopentadiene in 35 cc. CCl₄ to 13.1 g. I at below 30° and fractionating the mixture give 4-chlorocyclopenten-2-yl vinyl sulfide, b₇ 65°, which polymerizes readily when the solvent is distilled off at atm. pressure; on heating it 4 h. at 120° a dark thermoplastic resin is formed. Adding dropwise 10.4 g. styrene in 30 cc. CCl₄ to 13.1 g. I at below 25° and distilling the mixture give β-chlorophenethyl vinyl sulfide (III), b₈ 135°. Heating III 50 h. at 80° gives a thermoplastic styrene soft resin, soluble in chlorinated hydrocarbons. Heating III at 160° until HCl is no longer evolved (50 h.) gives a hard black resin containing 3% Cl. Adding dropwise 26.2 g. I in 10 cc. THF (THF) to 10.4 g. cycloöctatetraene in 20 cc. THF at 20° and distilling off the THF in vacuo give what may be 2,7-dichloro-5,8-bis(α-chloroethylmercapto)bicyclo[0.2.4]oct-3-ene (IV) as a viscous yellow-red oil. Heating IV 18 h. at 100° gives a hard nonthermoplastic polymer, (C₁₂H₁₄Cl₂S₂)_x. When IV is heated 10 h. at 160° a Cl-free nonthermoplastic resin of the composition (C₁₂H₁₂S₂)_x is obtained. Adding 13.1 g. I slowly at 35° to 6.6 g. CH₂(CN)₂ in 10 cc. THF causes the evolution of HCl; distilling off the THF in vacuo leaves a red oil which soon polymerizes with the evolution of heat and HCl, giving a soft resin which, on heating 24 h. at 100°, gives a dark brown thermoplastic polymer, (C₅H₅N₂ClS)_x. Refluxing 13.1 g. I and 7.4 g. THF 28 h. and distilling the mixture give δ-chlorobutyl α-chloroethanesulfenate, CH₂Cl(CH₂)₃OSCHClMe, b₁₂ 88°, decomposing to a red oil after a few days. Adding slowly CH₂N₂ [from 10 g. MeN(NO)CONH₂] to 8.5 g. I and distilling off the ether in vacuo give ClCH₂SCHClMe, b₁ 40°, mobile oil, decomposing on standing at 20°. Shaking 26 g. I 3 h. with 25 g. Hg and warming the decanted solution with fresh Hg 0.5 h. at 50° give (CH₂ClCH₂S)₂, yellow oil, b₉ 84°. Adding 15 g. I dropwise at 5° to 40 g. dry Me₂CO, warming the mixture 0.5 h. at 35°, and fractionating it give hexakis(α-chloroethylmercapto)acetone, b₂ 70°, which, heated 10 h. at 80°, polymerizes to a hard Cl-free resin. When equal parts of I and Me₂CO are mixed, heat and HCl are evolved; the mixture, heated 5 h. at 80° and fractionated, gives hexakis(ethylmercapto)acetone, light yellow oil, b₁₅ 53°. Mixing 12 g. PhAc and 13.1 g. I and distilling off the volatile parts in vacuo give a compound, MeCHClSCHBzSCHMeCHBzSCHClMe, which splits off HCl at 20°, completely after heating at 100°, giving a hard resin of the composition (C₂₂H₂₂O₂S₃)_x. Adding 13.1 g. I to 20 g. CH₂Ac₂ at below 30° and distilling the mixture give 3-(α-chloroethylmercapto)pentane-2,4-dione (V), b₁ 82°. Shaking 8 g. V with a small excess of 10% KOH 10 min. and adding 150 cc. H₂O give (3-vinylmercapto)pentane-2,4-dione, mobile oil, b_0.5 70°. Adding 39.3 g. I in 3 portions to 10 g. CH₂Ac₂, keeping the mixture several hrs., and distilling it give tris(α-chloroethylmercapto)pentane-2,4-dione, b₁₂ 104-7°. Similarly, equimolar amounts of I and AcCH₂CO₂Et give (as primary reaction product) Et α-(α’-chloroethylmercapto)acetoacetate (VI), which, heated 15 h. at 65°, gives Et α-(vinylmercapto)acetoacetate, yellow mobile oil, b₁₈ 115°. Adding 39.3 g. I slowly to 7.2 g. MeCOEt at 30° causes a strong evolution of HCl; the mixture is heated several hrs. at 100°, giving a Cl-free polymer, (C₂₀H₂₄OS₈)_x, as a nonthermoplastic black resin. Similarly, 39.3 g. I and 7 g. MeCOCH: CH₂ give MeCOCHClMe, b₂₈ 40°, and a resin which, heated 4 h. at 100°, gives a nonthermoplastic insoluble resin of the composition (C₁₄H₁₆OS₅)_x. Adding 6.5 g. I to 8 g. carbazole in 125 cc. warm xylene, heating the mixture 1.5 h. at 60°, and concentrating the filtered black solution in vacuo give (α-N-carbazolylethyl) (N-carbazolyl) sulfide, yellow crystals, m. 212° (decomposition), and a polymer which is obtained as the main product when 8 g. carbazole and 6.5 g. I are refluxed in 125 cc. xylene 2.5 h., the cooled solution is filtered, concentrated, filtered again, and evaporated, the residue extracted with CCl₄, and the residue of the CCl₄ extract heated 1 h. at 80°/12 mm. Adding dropwise 6.5 g. I in 15 cc. AcOH to 12.1 g. PhNMe₂ in 15 cc. AcOH, stirring the mixture 1 h. at 35°, adding 22.5 g. KOH in 200 cc. H₂O, extracting with ether, distilling off the PhNMe₂ from the residue of the dried ether extract, and recrystallizing the residue 3 times from EtOH give [α-(4-dimethylaminophenyl)ethyl] 4-dimethylaminophenyl sulfide, yellow needles, m. 125°. Adding in small portions with cooling 30 g. AlCl₃ to 13.1 g. I in 100 cc. C₆H₆, keeping the mixture overnight, distilling off about 50 cc. C₆H₆, pouring the residue into iced HCl, extracting with ether, and distilling the washed (NaOH) and dried organic solution at 30°/10 mm. leave Ph α-phenethyl sulfide, yellow crystals, m. 161°. Treating 11.4 g. CO(NHPh)₂ in 250 cc. CHCl₃ several hrs. with 13.1 g. I and distilling off the CHCl₃ give N,N’-diphenyl-N,N’-bis(α-chloroethylmercapto)thiourea-2HCl, m. 132°. Adding 13.1 g. I to 22.8 g. CO(NHPh)₂ in 120 cc. THF and distilling off the THF leave a viscous yellow soft resin which is heated 1 h. at 60°/12 mm. and has the composition (C₁₅H₁₆N₂Cl₂S₂)_x, soluble in CCl₄ and ether, and giving a clear solid film. Adding dropwise 13.1 g. I to 21.1 g. diphenylguanidine in 200 cc. CHCl₃ and distilling off the CHCl₃ give a polymer, (C₁₅H₁₇N₃Cl₂S)_x, as a tough thermoplastic film-forming red resin. Adding 13.1 g. I to 9.8 g. cyclohexanone in 50 cc. CCl₄ at below 40°, keeping the mixture 48 h. at 20°, and fractionating the solution give a colorless Cl-containing oil, b₈ 45°, which readily decompose, giving a Cl-containing dark red soft resin. When I and cyclohexanone are mixed without cooling, the mixture is heated 20 h. on a water bath, and the volatile portion is distilled off a red thermoplastic hard resin of the composition (C₈H₁₂OS)_x is obtained. Treating 9.4 g. PhOH in 50 cc. CHCl₃ with 13.1 g. I, distilling off the CHCl₃, and heating the residue 5 h. at 60° give a soft resin, containing 12.4% Cl, which after heating another 5 h. at 100° gives a Cl-free hard resin of the composition (C₈H₉OS)_x.

Chemische Berichte published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, Product Details of C4H8Cl2S2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics