Category: 1002-41-1

Williams, A. H. published the artcileThermal decomposition of bis(2-chloroethyl) sulfide, COA of Formula: C4H8Cl2S2, the publication is Journal of the Chemical Society (1947), 318-20, database is CAplus and MEDLINE.

The decomposition of (ClCH₂CH₂)₂S (I) was studied at 180°, the b.p (about 220°), 350°, and 450° (the last 2 by dropping I into a heated column packed with quartz rings). The products of decomposition at the above temperatures (in percentages of the initial weight of I) are: HCl 8.0, 21.2, 25.8, 31.5; C₂H₄ 4.2 11.2, 7.9, 10.4; C₂H₄Cl₂ 6.9, 11.1, -, -; H₂S -, -, 3.9, 5.2; CH₂:CHCl -, -, 14.6, 19.4; dithiane 1.3, 3.3, trace, trace; (ClC₂H₄)₂S₂ 5.8, 8.5, 2.0, -; I recovered 56.0, 14.2, 13.0, -; residue 12.2, 25.7, 31, 32; CS₂ -, -, 1, l. The residue of the 1st 2 experiments (after heating at 120°/4 mm.) contained 43-4% S and 17-17.5% Cl; that of the last 2 experiments was distributed over the interior of the column and could not be analyzed. The introduction of SiO₂ in the 2nd experiment did not produce any CH₂:CHCl but gave a small quantity of H₂S and some acceleration of the normal reaction; the decomposition of I in glass at the b.p. is not a surface reaction.

Journal of the Chemical Society 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 C19H14Cl2, COA of Formula: C4H8Cl2S2.

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

Strzelczyk, Marek published the artcileSynthesis of perhydro-1,2,5-dithiazepine derivatives of potential pharmacological activity, Application In Synthesis of 1002-41-1, the publication is Polish Journal of Pharmacology and Pharmacy (1984), 36(5), 473-84, database is CAplus and MEDLINE.

Perhydro-1,2,5-dithiazepines, e.g., I [R = H (II), Ph₂CH (III)] were prepared via cyclocondensation of ClCH₂CH₂SSCH₂CH₂Cl with amines. II and III showed spasmolytic, antihistaminic, and anticholinergic activities stronger than their analogs containing a perhydro-1,4-thiazepine system, but weaker than diphenhydramine.

Polish Journal of Pharmacology and Pharmacy 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 C15H14O3, Application In Synthesis of 1002-41-1.

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

Strzelczyk, Marek published the artcileSynthesis of 7-9-membered heterocyclic systems containing nitrogen and sulfur with expected pharmacological activity. I. Synthesis of perhydro-1,4,5-thiadiazocine, -1,4,6-thiadiazonine, and -1,2,5,7-dithiadiazonine derivatives, Name: 1,2-Bis(2-chloroethyl)disulfane, the publication is Acta Poloniae Pharmaceutica (1985), 42(4), 337-44, database is CAplus.

RCONHNHCOR (R = Me, Et, Ph, 2,4-Cl₂C₆H₃) were converted with NaNH₂ in C₆H₆ into the di-Na salts, which, condensed with Cl(CH₂)₂S(CH₂)₃Cl (I) in DMF, yielded 4,5-diacylperhydro-1,4,5-thiadiazocines II. 4,5-Bis(phenylsulfonyl)perhydro-1,4,5-thiadiazocine was prepared analogously from PhSO₂NHNHSO₂Ph. An analogous reaction with (MeNH)₂CO (III) gave thiadiazonine IV (X = CH₂), which was also obtained directly from I and III, refluxed in hexanol containing some Na₂CO₃. The latter method was also used to obtain the dimer IV (X = S) from III and (ClCH₂CH₂S)₂ (V), whereas meso-2,3-diaminobutane-2HCl, condensed under similar conditions with V, yielded VI.

Acta Poloniae Pharmaceutica 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 C8H11NO, Name: 1,2-Bis(2-chloroethyl)disulfane.

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

Pernot, Robert published the artcileThe reaction of ethylene with sulfur monochloride (S₂Cl₂) and with sulfur dichloride (S₂Cl₂ + Cl₂) in the preparation of bis(2-chloroethyl) sulfide (mustard gas), Safety of 1,2-Bis(2-chloroethyl)disulfane, the publication is Ann. chim. [12] (1946), 626-57, database is CAplus.

Crude mustard gas (I) as obtained in the Levinstein process is a clear yellow liquid, m. 10.5°, which does not deposit a trace of S when kept for over a year. On distillation in vacuo I gives 70% pure (ClCH₂CH₂)₂S.(II), m. 13.5°. I is only partially soluble in EtOH or ether. The m.p. is only slightly affected when byproducts are present. When 500 g. I is extracted with 500 cc. EtOH, 208 g. remains undissolved. On cooling the alc. solution, 130 g. II, m. 13.3°, crystallizes. When 500 g. I is cooled with ice-NaCl, 245 g. II, m. 12.5°, crystallizes. Distillation of 323 g. I gives 2 fractions, (a) 185 g., b₁₈ 110-15°, m. 13.3°, and (b) 40 g., b₁₈ 115-55°, m. 3.8°, the residue decomposing Redistillation of 40 g. of fraction a gives a fraction (c) 25 g., b₁₈ 110-15°, and 12 g., b₁₈ 120-35°, the latter being chiefly (ClCH₂CH₂)₂S₂ (III). Distillation of the EtOH solution gives II, but no III or (ClCH₂CH₂)₂S₃ (IV) is present. From the EtOH-insoluble part no definite product can be isolated even on distillation at 1 mm. It still contains a small amount of II which is removed by careful oxidation with H₂O₂, whereby II is oxidized to the H₂O-soluble sulfoxide while III and IV remain unchanged. The elementary composition of the residue after treatment with H₂O₂ corresponds to (ClCH₂CH₂)₂S₈ (V) which may be formed according to the following equation: 7S₂Cl₂ + 14C₂H₄ → 6 II + V. Treatment of 86 g. EtOH-insoluble product with moist NH₃ according to Felsing and Arenson (C.A. 15, 54) causes the separation of 16.5 g. S. The recovered product, now soluble in ether and C₆H₆, is free of N and has a composition corresponding to (ClCH₂CH₂)₂S₄ (VI). VI does not deposit S even after standing 6 mo. When VI is heated with S, the latter dissolves and seps. again on cooling. In an attempt to hydrolyze VI with alc. KOH no definite compound is formed. When VI is treated with Me₂CO, S is deposited with the formation of IV, m. 27°. IV is also formed when VI is treated with steam at 100 mm. An attempt to oxidize IV with BzO₂H, to transfer it into the iodine compound by heating it with NaI in a sealed tube, or to condense IV with PhONa or BzONa failed. Distillation of 50 g. IV at 1 mm. gives 40 g. yellow liquid, b₁ 120-35°. Redistillation of the latter gives 2 fractions, (d) 10 g., b₁ up to 120°, and (e) 28 g., b₁ 120-6°, containing chiefly IV, m. 26.5°. IV prepared according to Mann, et al. (C.A. 15, 2413), m. 25°; the mixed m.p. of the 2 preparations is 26°. When IV is heated with the theor. amount of S to form VI, the S dissolves but seps. again on cooling. IV when distilled at 40 mm. gives a small amount of III, b. 160-5°, which is not attacked by H₂O₂. When distilled at atm. pressure III gives a very small amount of II. These results show that III has the structure (ClCH₂CH₂S)₂ and not (ClCH₂CH₂)₂S:S, while IV has the structure ClCH₂CH₂S(:S)SCH₂CH₂Cl. When 220 g. EtOH-insoluble product is extracted 5 times with 200 cc. pure and dry Me₂CO and the Me₂CO is evaporated, 80 g. of yellow oil is obtained from which some (ClCH₂CH₂)₂SO crystallizes. The residual oil has a composition corresponding to (ClCH₂CH₂)₂S₅ (VII) and is insoluble in EtOH, petr. ether, and AcOH. Pyridine precipitates 8.5 g. S from 43 g. VII. Evaporation of the pyridine leaves an oil which on distillation at 3 mm. gives a mixture of III and IV. The Me₂CO-insoluble part (140 g.), when cooled, deposits 16 g. S. The filtrate consists of a polysulfide or a mixture of polysulfides high in S content (75.7-6.7%). The hypothesis that II is formed according to the equation S₂Cl₂ + 2C₂H₄ → II + S is not substantiated by the action of C₂H₄ upon S₅Cl₂. When 580 g. S₅Cl₂ is treated with C₂H₄, 733 g. reaction product is obtained from which 207 g. S deposits, giving 526 g. reaction product. From 342 g. S₂Cl₂, which equals 580 g. S₅Cl₂, and 142 g. C₂H₄, 484 g. reaction product is calculated while 526 g. is obtained. These results indicate that S₅Cl₂ reacts in the same way as S₂Cl₂. The following reaction mechanism is proposed: S₂Cl₂ + 3C₂H₄ gives a sesquimustard gas, (CH₂SCH₂CH₂Cl)₂ (VIII). VIII reacts with S₂Cl₂ to give 1 mol. II and ClSS₂CH₂CH₂Cl (IX); IX + C₂H₄ → IV. IV + S₂Cl₂ → Cl.S.CH₂CH₂Cl (X) + ClS₄CH₂CH₂Cl (XI); XI + C₂H₄ → II + VI, etc. SCl₂ + C₂H₄ gives 85% crude reaction product (XII), m. 5-8°. Distillation of 109.5 g. XII, m. 5.5°, gives 3 fractions: (f) 97.5 g., b₁₀ 93-6°, m. 10°; (g) 4.5 g., b₁₀ 96-105°; and 3.5 g. residue. Redistillation of 90 g. f gives a fraction, 76.5 g., b₁₂ 97-8°, m. 10°, which on redistillation gives 62.3 g., b₁₃ 101-2°, m. 10.2°, and 11.4 g., b₁₅ 102-4°, m. 11.8°. This indicates that with II other products come over. Because under the conditions used, SCl₂ can be considered to be a solution of Cl in a mixture of SCl₂ and S₂Cl₂, byproducts containing α-chlorinated compounds are formed which split off HCl with formation of ClCH:CHSCH₂CH₂Cl (XIII). II containing 8.8% XIII m. 9.9°. When SCl₂ in a 10% CCl₄ solution and C₂H₄ are allowed to react and the reaction product is distilled after the CCl₄ has been removed at 120°, II, b₁₀ 93.5-4°, m. 10.8°, is obtained. When 800 g. of the reaction product is extracted with EtOH only 31 g. insoluble product (XIV) is obtained. When Cl is passed into 250 g. XIV, the temperature rises to 45-50°. As soon as the temperature drops to room temperature the Cl current is stopped and the reaction product distilled in vacuo. Up to 70°/15 mm. the S-Cl compounds distill, and between 98° and 100° a few cc. of a turbid liquid distills. When C₂H₄ is passed at 30-40° into the residue, a vigorous reaction takes place. After the active Cl in the residue has disappeared, 303 g. of a clear red solution is obtained. Distillation of 238 g. of this solution gives 3 fractions: (h) 12.6 g., b₁₃ 40-97°; (i) 76.6 g., b₁₃ 97-107°; (j) 8.2 g., b₁₃ 107-25°. Redistillation of i gives a product, b₁₃ 98-101°, m. 8.6°. Oxidation of 4.3 g. of this product with H₂O₂ at 50° in AcOH gives 1.2 g. of a sulfoxide, m. 108°, which when mixed with the sulfoxide of II, m. 108°. These results indicate that the Cl splits the polysulfides, ClCH₂CH₂S(:S_x)S(:S_y)CH₂CH₂Cl, to give 2 mols. X, while the S is converted into SCl₂ which again reacts with C₂H₄ with excess formation of a certain amount of II. On the other hand, the Cl also reacts with X, giving rise to the formation of XIV.

Ann. chim. [12] 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, Safety of 1,2-Bis(2-chloroethyl)disulfane.

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

Masamba, W. R. L. published the artcileDetection of trace amounts of chemical warfare agents in paint by gas chromatography and gas chromatography-mass spectrometry, COA of Formula: C4H8Cl2S2, the publication is Malawi Journal of Science & Technology (2001), 47-55, database is CAplus.

The chem. warfare agents pinacoly methylphosphonofluoridate (soman), bis[(2-chloroethylthio)ethyl] ether (O mustard), and tris(2-chloroethyl)amine (nitrogen mustard) and low levels of bis(2-chloroethyl) sulfide (mustard gas, H), 1,2-bis(2-chloroethylthio)ethane (Sesquimustard), and bis(2-chloroethyl) disulfide were detected by gas chromatog. and gas chromatog.-mass spectrometry in a paint sample that had been prepared by spiking soman, O mustard, and nitrogen mustard to simulate a case where chem. warfare agents were absorbed into a paint matrix. The results show that gas chromatog. and gas chromatog.-mass spectrometry can be used for the detection of such chem. warfare agents in paint samples.

Malawi Journal of Science & Technology 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

Debowski, Zbigniew published the artcileTechnology of aminoiminomethanesulfinic acid preparation, Formula: C4H8Cl2S2, the publication is Przemysl Chemiczny (1965), 44(2), 82-5, database is CAplus.

Aminoiminomethanesulfinic acid N₂NC(:NH)SO₂(OH) (I), m. 112-15°, was obtained when 2400 ml. 30% H₂O₂ was dropwise added with continuous stirring to 760 g. thiourea in 500 ml. H₂O and 100 ml. N HCl at 4°. The influence of temperature and H₂O₂ concentration on the yield and purity of I was examined and results shown in tables. The drying process of I was also examined The dependence of drying efficiency upon the temperature, as well as the H₂O content upon the velocity and time of drying at 55° under reduced and atm. pressure, were evaluated and their curves plotted. The mechanism of thiourea oxidation to I based on an analysis of its decomposition products was proposed.

Przemysl Chemiczny 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, Formula: C4H8Cl2S2.

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

Dawson, Thomas P. published the artcileReactions of certain halogen-substituted aryl, alkyl and dialkyl sulfides with benzylamines, Synthetic Route of 1002-41-1, the publication is Journal of the American Chemical Society (1933), 2070-5, database is CAplus.

The following sulfides, ClCH₂CH₂SR, are liquids of penetrating odor (R is given): Et, b₄₇ 63-5°, d₄²⁵ 1.0663, η × 10³ (C. G. S. units at 25°) 9.89; Pr, b₂ 43-5°, d. 1.0349, η 12.92; Bu, b₁ 58-9°, d. 1.0122, η 15.25; iso-Am, b₁ 68°, d. 0.9899, η 18.55; Ph, b_0.637 88-9°, d. 1.1769, η 30.86, PhCH₂, b_1.01 113-5°, d. 1.1479, η 50.61; BrCH₂CH₂SEt, b₆ 57-8°, d. 1.3908, 15.55. MeCHClCH₂SEt, b₁₇ 60°, d. 1.0265, 11.15; Cl(CH₂)₃SEt, b₁₇ 72°, d. 1.0427, η 13.30. (MeCHClCH₂)₂S, b₇ 94-5°, d. 1.1569, η 33; (ClCH₂CH₂CH₂)₂S, b₇ 111-2°, d. 1.1774, η 41.87. (ClCH₂)₂S, b₁₁ 51°, d. 1.4065, η 18.09. (ClC₂H₄)₂S₂, b₁₀ 124-7°, d₄²⁰ 1.3375, η 83.06. β-Chloroethyl α,β-dichlorovinyl sulfide, b₄ 79.5-80.5°, d₄²⁰ 1.4581, η 31.98. Et allyl sulfide, b. 115-6°, d₄²⁰ 0.8676, η 5.97. These sulfides were treated with PhCH₂NH₂ and Na₂CO₃ in absolute EtOH; the b. ps. are for the free bases, the m. ps. for the HCl salts: β-benzylaminoethyl Et sulfide, b₁₃ 162-4°, m. 214-5°; Pr derivative, b₁₃ 167-9°, m. 175°; Bu derivative, b₁₃ 172-230°, m. 152-3°; iso-Am derivative, b₁₇ 190-250°, m. 161-2°; Ph derivative, m. 152-3°; β-benzylaminopropyl Et sulfide, b₁₁ 157-8°, m. 115°; γ-isomer, b₁₂ 163-5°, m. 172°; 3-benzyl-1,3-thiazetidine, b₁₆ 175-85°, m. 201-3°; bis(β-benzylaminopropyl) sulfide, m. 239-40°; bis(β-benzylaminoethyl) disulfide, m. 269°; β-benzylaminoethyl α-(and β-)chlorovinyl sulfide, m. 211-2°; β-benzylaminoethyl α,β-dichlorovinyl sulfide, m. 174-6°. The results may be regarded as further substantiating the condensation theory of vesicant action but they entirely eliminate thiazane formation as an important factor and appear to demand a new limitation-that of a reactive halogen on the β-C atom.

Journal of the American Chemical Society 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

Bennett, George Macdonald published the artcileβ,β’-Dichlorodiethyl disulfide, Related Products of chlorides-buliding-blocks, the publication is Journal of the Chemical Society, Transactions (1921), 418-25, database is CAplus.

The behavior of S₂Cl₂ and C₂H₄ has been the subject of some controversy, the issue being whether a monosulfide or a disulfide is formed. Bennett has reinvestigated the reaction at 30-35° and concludes that the liquids are two-phase systems in which the continuous phase is nearly pure S(C₂H₄Cl)₂ and the disperse phase a liquid consisting chiefly of S. The varying behavior on dilution with Et₂O, etc., may be due to different degrees of dispersion. 50 cc. S₂Cl₂ gave 111 g. of a pale amber-colored liquid, d₁₅ 1.373, m. 5-6°; the relative viscosity at 15° was 10.25. which is characteristic of liquid-liquid 2-phase systems. The product b₂₀ 110-20°. The addition of 20 cc. dry Et₂O to 30 cc. of the liquid before distillation produced no separation into 2 phases. 100 cc. Et₂O caused the separation of 4.7 g. of a S-yellow oil, which was impure S. Heating in a stream of dry air for an hr. also caused the separation of S. In each case the m. p. of the sulfide was unaffected. Attempts to prepare the emulsion from the sulfide and S were unsuccessful. SHCH₂CH₂OH (Ann. 124, 257) was prepared by melting 225 g. crystalline Na₂S on the H₂O bath, saturating with H₂S, cooling to 50° and stirring in 70 g. ClCH₂CH₂OH. It b₁₈ 58°, d₄²⁰ 1.1153, n_D²⁰ 1.4443. This was oxidized to β,β’-dichlorodiethyl disulfide C₄H₈Cl₂S₂, by H₂O₂, FeCl₃ or NaBrO, straw-colored oil, b₃₀ 155°, d₄²⁰ 1.3375, (η/η_H2O)₂₀, 6.08. It resembles the monosulfide in many of its properties. Its vesicant action was 1/3 that of the monosulfide. Boiled with PhONa, it yields β,β’-diphenoxydiethyl disulfide, small, silvery plates, m. 96-7°. Na₂S gives S(C₂H₄)₂S. On oxidation it yields C₂H₄O₃ClSNa.H₂O (Ann. 223, 213).

Journal of the Chemical Society, Transactions 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, Related Products of chlorides-buliding-blocks.

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

Gu, Huifen published the artcileSeparation and identification of mustard gas compounds in diesel fuel, Category: chlorides-buliding-blocks, the publication is Fenxi Ceshi Xuebao (1995), 14(3), 6-9, database is CAplus.

Separation and identification of mustard and mustard disulfide in diesel fuel and aromatic compound mixtures are presented. Samples were prepurified by column chromatog. using hexane as eluate, and interfering matrixes were removed. Pure compounds were obtained with thin-layer chromatog. by developing the TLC plate twice in hexane and identified with gas chromatog.-mass spectrometry and NMR spectrometry.

Fenxi Ceshi Xuebao 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

Li, Nan published the artcileAnalysis of long chain sulphur mustard and related compounds by gas chromatography-mass spectrometry, Related Products of chlorides-buliding-blocks, the publication is Fenxi Shiyanshi (2003), 22(1), 86-89, database is CAplus.

The identification of sulfur-containing mustards was studied by gas chromatog.-mass spectrometry. Under the applied conditions, the anal. species were separated effectively with the capillary columns coated with SE-54 stationary phases from the mixture solution Electron-impact pos.-ion mass spectral cleavage mechanisms of sulfur-mustards were discussed in detail. From the mass spectra, general fragmentation pathways of these compounds were derived.

Fenxi Shiyanshi 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, Related Products of chlorides-buliding-blocks.

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