Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Disulfur dichloride: Difference between pages
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Disulfur_dichloride|oldid=476442658}} 476442658] of page [[Disulfur_dichloride]] with values updated to verified values.}} |
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{{Chembox |
{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 470454517 |
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| Watchedfields = changed |
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| ImageFile = Disulfur-dichloride-2D-dimensions.png |
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| verifiedrevid = 476993527 |
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| ImageSize = 220px |
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| ImageFile = Disulfur-dichloride-2D-dimensions.png |
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| ImageName = Wireframe model of disulfur dichloride |
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| ImageFileL1 = Disulfur-dichloride-3D-balls.png |
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| ImageFileL1 = Disulfur-dichloride-3D-balls.png |
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| ImageSizeL1 = 125px |
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| ImageNameL1 = Ball and stick model of disulfur dichloride |
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| ImageCaptionR1 = {{legend|yellow|Sulfur, S}}{{legend|lime|Chlorine, Cl}} |
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| ImageFileR1 = Disulfur-dichloride-3D-vdW.png |
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| ImageFileR1 = Disulfur-dichloride-3D-vdW.png |
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| ImageSizeR1 = 115px |
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| ImageNameR1 = Spacefill model of disulfur dichloride |
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| ImageFile2 = Дитиодихлорид.jpg |
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| IUPACName = Disulfur dichloride |
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| IUPACName = Disulfur dichloride<br>Dichlorodisulfane |
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| SystematicName = Chlorosulfanyl thiohypochlorite |
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| OtherNames = Bis[chloridosulfur](''S''–''S'')<br /> |
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Dimeric sulfenic chloride |
| OtherNames = {{ubl|Bis[chloridosulfur](''S''–''S'')|Dimeric sulfenic chloride|Sulfur monochloride (incorrect name)}} |
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| Section1 = {{Chembox Identifiers |
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Sulfur monochloride |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/Cl2S2/c1-3-4-2 |
| StdInChI = 1S/Cl2S2/c1-3-4-2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PXJJSXABGXMUSU-UHFFFAOYSA-N |
| StdInChIKey = PXJJSXABGXMUSU-UHFFFAOYSA-N |
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| CASNo = 10025-67-9 |
| CASNo = 10025-67-9 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1_Ref = {{cascite|changed|??}} |
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| CASNo1 = 85408-26-0 |
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| CASNo1_Comment = (isobutenate) |
| CASNo1 = 85408-26-0 |
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| CASNo1_Comment = (isobutenate) |
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| DrugBank = DB14647 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 24807 |
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| UNII = NJ7YR2EV0D |
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| PubChem_Ref = {{Pubchemcite}} |
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| |
| PubChem = 24807 |
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| ChemSpiderID = 23192 |
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| PubChem1_Comment = (isobutenate) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem1_Ref = {{Pubchemcite}} |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 23192 |
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| ChemSpiderID1 = 19158348 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1_Comment = (isobutenate) |
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| ChemSpiderID1 = 152167 |
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| EINECS = 233-036-2 |
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| ChemSpiderID1_Comment = (isobutenate) |
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| UNNumber = 3390 |
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| ChemSpiderID1_Ref = {{Chemspidercite}} |
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| MeSHName = Sulfur+monochloride |
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| EINECS = 233-036-2 |
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| RTECS = WS4300000 |
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| SMILES = ClSSCl |
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| MeSHName = Sulfur+monochloride |
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| InChI = 1/Cl2S2/c1-3-4-2 |
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| RTECS = WS4300000 |
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| InChIKey = PXJJSXABGXMUSU-UHFFFAOYAK |
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| SMILES = ClSSCl |
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}} |
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| InChI = 1/Cl2S2/c1-3-4-2 |
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| Section2 = {{Chembox Properties |
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| InChIKey = PXJJSXABGXMUSU-UHFFFAOYAK |
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| Formula = {{chem2|S2Cl2}} |
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}} |
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| S=2|Cl=2 |
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| Section2 = {{Chembox Properties |
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| Appearance = Light-amber to yellow-red, oily liquid<ref name=PGCH/> |
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| Formula = S<sub>2</sub>Cl<sub>2</sub> |
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| Odor = pungent, nauseating, irritating<ref name=PGCH/> |
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| MolarMass = 135.04 g/mol |
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| Density = 1.688 g/cm<sup>3</sup> |
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| Appearance = yellow liquid |
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| Solubility = Decomposes, with loss of [[hydrogen Chloride|HCl]] |
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| Density = 1.688 g/cm<sup>3</sup> |
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| SolubleOther = Soluble in [[ethanol]], [[benzene]], [[diethyl ether|ether]], [[tetrahydrofuran|THF]], [[chloroform]], [[carbon tetrachloride|{{chem2|CCl4}}]]<ref name="Patnaik">Pradyot Patnaik. ''Handbook of Inorganic Chemicals''. McGraw-Hill, 2002, {{ISBN|0-07-049439-8}}</ref> |
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| Solubility = decomp with loss of HCl |
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| MeltingPtC = −80 |
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| SolubleOther = soluble in [[ethanol]], [[benzene]], [[ether]], [[chloroform]], [[carbon tetrachloride|CCl<sub>4</sub>]]<ref name="Patnaik">Pradyot Patnaik. ''Handbook of Inorganic Chemicals''. McGraw-Hill, 2002, ISBN 0070494398</ref> |
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| BoilingPtC = 137.1 |
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| |
| RefractIndex = 1.658 |
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| VaporPressure = 7 mmHg (20 °C)<ref name=PGCH/> |
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| RefractIndex = 1.658 |
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<!-- |
<!--| Dielectric Constant = 4.79<ref name=Ullmann></ref>--> |
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| MagSus = −62.2·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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}} |
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| Section3 = {{Chembox Structure |
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| Section3 = {{Chembox Structure |
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| Coordination = gauche |
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| Coordination = 2 at [[sulfur]] atoms |
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| Dipole = 1.60 [[Debye|D]] <ref name="Patnaik"/> }} |
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| MolShape = [[Conformational isomerism|gauche]] |
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| Section7 = {{Chembox Hazards |
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| PointGroup = [[Molecular symmetry#Common point groups|C<sub>2</sub>]] |
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| ExternalMSDS = [http://www.inchem.org/documents/icsc/icsc/eics0958.htm ICSC 0958] |
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| Dipole = 1.60 [[Debye|D]]<ref name="Patnaik"/> }} |
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| EUIndex = 016-012-00-4 |
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| Section7 = {{Chembox Hazards |
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| EUClass = Toxic ('''T''')<br />Harmful ('''Xn''')<br />Corrosive ('''C''')<br />Dangerous for the environment ('''N''') |
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| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0958.htm ICSC 0958] |
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| NFPA-H = 2 |
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| NFPA-H = 2 |
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| NFPA-R = 1 |
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| NFPA-F = 1 |
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| RPhrases = {{R14}}, {{R20}}, {{R25}}, {{R29}}, {{R35}}, {{R50}} |
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| |
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| FlashPt = 118.5 °C |
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| HPhrases = {{H-phrases|301|314|332|400}} |
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| Autoignition = 234 °C |
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| PPhrases = {{P-phrases|260|261|264|270|271|273|280|301+310|301+330+331|303+361+353|304+312|304+340|305+351+338|310|312|321|330|363|391|405|501}} |
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}} |
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| FlashPtC = 118.5 |
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| Section8 = {{Chembox Related |
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| AutoignitionPtC = 234 |
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| OtherFunctn = [[Sulfur dichloride]]<br />[[Thionyl chloride]]<br />[[Sulfuryl chloride]] |
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| IDLH = 5 ppm<ref name=PGCH>{{PGCH|0578}}</ref> (1 ppm = 5.52 mg/m<sup>3</sup>) |
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| Function = sulfur chlorides |
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| REL = C 1 ppm (5.52 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| OtherCpds = [[Disulfur difluoride]]<br />[[Disulfur dibromide]] |
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| PEL = TWA 1 ppm (5.52 mg/m<sup>3</sup>)<ref name=PGCH/> |
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}} |
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| LCLo = 150 [[Parts-per notation|ppm]] (mouse, 1 min) (1 ppm = 5.52 mg/m<sup>3</sup>)<ref>{{IDLH|10025679|Sulfur monochloride}}</ref> |
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}} |
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| Section8 = {{Chembox Related |
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| OtherFunction = {{ubl|[[Sulfur dichloride]]|[[Thionyl chloride]]|[[Sulfuryl chloride]]}} |
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| OtherFunction_label = sulfur chlorides/oxychlorides |
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| OtherCompounds = {{ubl|[[Hydrogen disulfide]]|[[Disulfur difluoride]]|[[Disulfur dibromide]]|[[Disulfur diiodide]]|[[Dimethyl disulfide]]|[[Diphenyl disulfide]]|[[Diselenium dichloride]]}} |
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}} |
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}} |
}} |
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'''Disulfur dichloride''' (or '''disulphur dichloride''' by the [[British English]] spelling) is the [[inorganic compound]] of [[sulfur]] and [[chlorine]] with the [[Chemical formula|formula]] {{chem2|S2Cl2}}.<ref>Holleman, A. F.; Wiberg, E. ''Inorganic Chemistry'' Academic Press: San Diego, 2001. {{ISBN|0-12-352651-5}}.</ref><ref>{{OrgSynth | first1 = W. W. | last1 = Hartman | first2 = L. A. | last2 = Smith | first3 = J. B. | last3 = Dickey | title = Diphenylsulfide | collvol = 2 | collvolpages = 242 | volume = 14 | pages = 36 | year = 1934 | prep=cv2p0242}}</ref><ref>R. J. Cremlyn ''An Introduction to Organosulfur Chemistry'' John Wiley and Sons: Chichester (1996). {{ISBN|0-471-95512-4}}</ref><ref>{{cite journal| author=Garcia-Valverde M., Torroba T.|title= Heterocyclic chemistry of sulfur chlorides – Fast ways to complex heterocycles |journal= European Journal of Organic Chemistry|volume=2006| pages= 849–861|year= 2006|doi= 10.1002/ejoc.200500786| issue=4}}</ref> It is an amber oily liquid. |
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Sometimes, this compound is incorrectly named ''sulfur monochloride'' (or ''sulphur monochloride'' by the British English spelling), the name implied by its [[empirical formula]] SCl. |
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{{chem2|S2Cl2}} has the structure implied by the formula {{chem2|Cl\sS\sS\sCl}}, wherein the [[dihedral angle]] between the {{chem2|Cl^{''a''}\sS\sS}} and {{chem2|S\sS\sCl^{''b''}|}} planes is 85.2°. This structure is referred to as [[Conformational isomerism|gauche]], and is akin to that for [[Hydrogen peroxide|{{chem2|H2O2}}]]. A rare [[isomer]] of {{chem2|S2Cl2}} is {{chem2|S\dSCl2}} (thiothionyl chloride); this isomer forms transiently when {{chem2|S2Cl2}} is exposed to [[UV-radiation]] (see [[thiosulfoxide]]s). |
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==Synthesis, basic properties, reactions== |
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Disulfur dichloride is a yellow liquid that fumes in moist air due to reaction with water: |
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:{{chem2|16 S2Cl2 + 16 H2O → 8 SO2 + 32 HCl + 3 S8}} |
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It is produced by partial chlorination of elemental [[sulfur]]. The reaction proceeds at usable rates at room temperature. In the laboratory, chlorine gas is led into a flask containing elemental sulfur. As disulfur dichloride is formed, the contents become a golden yellow liquid:<ref>F. Fehér "Dichlorodisulfane" in ''Handbook of Preparative Inorganic Chemistry'', 2nd Ed. Edited by G. Brauer, Academic Press, 1963, NY. Vol. 1. p. 371.</ref> |
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:{{chem2|S8 + 4 Cl2 → 4 S2Cl2}}, ''ΔH'' = −58.2 kJ/mol |
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Excess chlorine produces [[sulfur dichloride]], which causes the liquid to become less yellow and more orange-red: |
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:{{chem2|S2Cl2 + Cl2 ⇌ 2 SCl2}}, ''ΔH'' = −40.6 kJ/mol |
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The reaction is reversible, and upon standing, {{chem2|SCl2}} releases chlorine to revert to the disulfur dichloride. Disulfur dichloride has the ability to dissolve large quantities of sulfur, which reflects in part the formation of [[polysulfane]]s: |
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:{{chem2|8 S2Cl2 + ''n'' S8 → 8 S_{''n''+2}Cl2}} |
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Disulfur dichloride can be purified by distillation from excess elemental sulfur. |
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{{chem2|S2Cl2}} also arises from the chlorination of [[Carbon disulfide|{{chem2|CS2}}]] as in the synthesis of [[thiophosgene]] or [[carbon tetrachloride]]. |
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===Reactions=== |
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{{chem2|S2Cl2}} [[hydrolyze]]s to [[sulfur dioxide]] and elemental [[sulfur]]. When treated with [[hydrogen sulfide]], [[polysulfane]]s are formed as indicated in the following idealized formula: |
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:{{chem2|2 H2S + S2Cl2 → [[Hydrogen tetrasulfide|H2S4]] + 2 HCl}} |
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It reacts with [[ammonia]] to give [[tetrasulfur tetranitride]] as well as [[heptasulfur imide]] ({{chem2|S7NH}}) and related S−N rings {{chem2|S_{8−''n''}(NH)_{''n''}|}} (''n'' = 2, 3).<ref name=Tyree>{{cite book |doi=10.1002/9780470132401 |chapter= Chapter VI |title=Inorganic Syntheses |year=1967 |last1=Tyree Jr. |first1=S. Y.|isbn=9780470131688}}</ref> |
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:{{chem2|16 NH3 + 6 S2Cl2 → S4N4 + S8 + 12 NH4Cl}} |
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With primary and secondary [[alkoxide]] equivalents, it forms disulfoxylate esters: |
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:2 ROH + S<sub>2</sub>Cl<sub>2</sub> + 2 NEt<sub>3</sub> → (R–O–S)<sub>2</sub> + 2 [HNEt<sub>3</sub>]Cl |
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In principle the subsequent addition of base should give [[sulfoxylate]] esters, but typically induces disproportionation to aldehydes and alcohols instead.<ref>{{unbulleted list citebundle|{{cite journal|doi=10.1021/jo01019a044|journal=JOC|volume=30|number=8|date=1 Aug 1965|orig-date=11 Jan 1965|title=Organic Esters of Bivalent Sulfur I: Dialkoxy Disulfides|first1=Q. E.|last1=Thompson|first2=M. M.|last2=Crutchfield|first3=M. W.|last3=Dietrich|first4=E.|last4=Pierron}}|Thompson, Q. E. "——— III: Sulfoxylates". ''[[Ibid]]''. {{doi|10.1021/jo01019a046}}}}</ref> |
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==Applications== |
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{{chem2|S2Cl2}} has been used to introduce [[Organosulfur chemistry|C−S bonds]]. In the presence of [[aluminium chloride]] ({{chem2|AlCl3}}), {{chem2|S2Cl2}} reacts with [[benzene]] to give diphenyl sulfide: |
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:{{chem2|8 S2Cl2 + 16 [[Benzene|C6H6]] → 8 [[Diphenyl sulfide|(C6H5)2S]] + 16 [[Hydrogen chloride|HCl]] + [[Octasulfur|S8]]}} |
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[[Aniline]]s (1) react with {{chem2|S2Cl2}} in the presence of [[Sodium hydroxide|NaOH]] to give 1,2,3-benzodithiazolium chloride (2) ([[Herz reaction]]) which can be transformed into ''ortho''-aminothiophenolates (3), these species are precursors to [[thioindigo]] [[dye]]s. |
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:[[File:Herzrxn.png|700px]] |
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It is also used to prepare [[Bis(2-chloroethyl) sulfide|mustard gas]] via [[ethylene]] at 60 °C (the Levinstein process): |
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:{{chem2|8 S2Cl2 + 16 [[ethylene|H2C\dCH2]] → 8 (ClCH2CH2)2S + S8}} |
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Other uses of {{chem2|S2Cl2}} include the manufacture of [[sulfur dye]]s, [[insecticides]], and [[synthetic rubber]]s. It is also used in cold [[vulcanization]] of [[rubbers]], as a [[polymerization]] [[catalyst]] for [[vegetable oils]] and for hardening [[soft wood]]s.<ref name=Ullmann>{{cite book |doi=10.1002/14356007.a25_623 |chapter=Sulfur Halides |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2000 |last1=Lauss |first1=Hans-Dietrich |last2=Steffens |first2=Wilfried |isbn=3527306730}}</ref> |
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==Safety and regulation== |
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{{chem2|S2Cl2}} can be used to produce [[bis(2-chloroethyl)sulfide]] {{chem2|S(CH2CH2Cl)2}}, known as the mustard gas:<ref name = Ullmann/> |
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:{{chem2|S2Cl2 + 2 [[Ethylene|H2C\dCH2]] → S(CH2CH2Cl)2 + [[Sulfur|"S"]]}} |
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Consequently, it is listed in Schedule 3 of the [[Chemical Weapons Convention]]. Facilities that produce and/or process and/or consume scheduled chemicals may be subject to control, reporting mechanisms and inspection by the [[Organisation for the Prohibition of Chemical Weapons]]. |
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==References== |
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{{reflist}} |
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{{Commons category|Disulfur dichloride}} |
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{{sulfur compounds}} |
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{{Chlorides}} |
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[[Category:Disulfides]] |
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[[Category:Sulfur chlorides]] |