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Revision as of 13:43, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 476810479 of page Sulfur_mustard for the Chem/Drugbox validation project (updated: '').  Latest revision as of 07:19, 17 February 2024 edit Citation bot (talk | contribs)Bots5,457,383 edits Added date. | Use this bot. Report bugs. | Suggested by Abductive | Category:World War I chemical weapons | #UCB_Category 1/19 
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{{short description|Chemical compound formerly used in warfare}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 415234626 | verifiedrevid = 477002998
| Name = Sulfur mustard | Name = Mustard gas
| ImageFile = Sulfur-mustard-2D-skeletal.png | ImageFile = Sulfur-mustard-2D-skeletal.svg
| ImageFile1 = Sulfur-mustard-3D-balls.png | ImageFile1 = Sulfur-mustard-3D-balls.png
| ImageFile2 = Sulfur-mustard-3D-vdW.png | ImageFile2 = Sulfur-mustard-3D-vdW.png
| IUPACName = bis(2-chloroethyl) sulfide | PIN = 1-Chloro-2-ethane
| OtherNames = Iprit<br />Schwefel-Lost<br />Lost<br />Mustard gas<br />Senfgas<br />Yellow Cross Liquid<br />Yperite<br />Distilled Mustard<br />Mustard T- mixture | OtherNames = Bis(2-chloroethyl) sulfide<br />HD <br />Iprit<br />Schwefel-LOST<br />Lost<br />Sulfur mustard<br />Senfgas<br />Yellow cross liquid<br />Yperite<br />Distilled mustard<br />Mustard T- mixture<br />1,1'-thiobis<br />Dichlorodiethyl sulfide
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| Beilstein = 1733595
| PubChem = 10461
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106142 | ChemSpiderID = 21106142
| EC_number = 684-527-7
| InChI = 1/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2 | InChI = 1/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2
| InChIKey = QKSKPIVNLNLAAV-UHFFFAOYAK | InChIKey = QKSKPIVNLNLAAV-UHFFFAOYAK
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 455341 | ChEMBL = 455341
| Gmelin = 324535
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2 | StdInChI = 1S/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2
Line 23: Line 27:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 505-60-2 | CASNo = 505-60-2
| UNII_Ref = {{fdacite|correct|FDA}}
| CA Index name 1,1'-thiobis
| UNII = T8KEC9FH9P
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19164 | KEGG = C19164
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 25434 | ChEBI = 25434
| SMILES = ClCCSCCCl | SMILES = ClCCSCCCl
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=4|H=8|Cl=2|S=1 | C=4 | H=8 | Cl=2 | S=1
| Appearance = Colorless if pure.<br />Normally ranges from<br />pale yellow to dark brown.<br />Slight garlic or horseradish type odour<ref name="FM 3-8">'''FM 3–8 Chemical Reference handbook'''; US Army; 1967</ref> | Appearance = Colorless if pure. Normally ranges from pale yellow to dark brown. Slight garlic or horseradish type odor.<ref name="FM 3-8">FM 3–8 Chemical Reference handbook, US Army, 1967</ref>
| Density = 1.27 g/mL, liquid | Density = 1.27 g/mL, liquid
| Solubility = 7.6 mg/L at 20°C<ref name="opcw.org">. Organisation for the Prohibition of Chemical Weapons. Accessed June 8, 2010.</ref>
| Solubility = Negligible
| SolubleOther = ], ]s, ]s, ]s, ]
| MeltingPt = 14.4 °C, 287.6 K, 57.9 °F
| MeltingPtC = 14.4
| BoilingPtC = 217 | BoilingPtC = 217
| BoilingPt_notes = begins to decompose at {{convert|217|C|F}} and boils at {{convert|218|C|F}}
| Boiling_notes = decomposes
⚫ }}
}}| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS =
| ExternalSDS =
| MainHazards = Very toxic ('''T+''')<br />Dangerous for the environment ('''N''')<br />]
| MainHazards = Flammable, toxic, vesicant, carcinogenic, mutagenic
| GHS_ref = <ref>{{cite web| url = https://pubchem.ncbi.nlm.nih.gov/compound/10461| title = Pubchem}}</ref>
| GHSPictograms = {{GHS06}}{{GHS07}}
| GHSSignalWord = Danger
| PPhrases = {{P-phrases|P260|P261|P262|P264|P270|P271|P280|P284|P301+P310|P302+P350|P302+P352|P304+P340|P305+P351+P338|P310|P312|P320|P321|P322|P330|P332+P313|P337+P313|P361|P362|P363|P403+P233|P405|P501}}
| HPhrases = {{H-phrases|H300|H310|H315|H319|H330|H335}}
| NFPA-H = 4 | NFPA-H = 4
| NFPA-F = 1 | NFPA-F = 1
| NFPA-R = 1 | NFPA-R = 1
| FlashPt = 105 °C | FlashPtC = 105
}}
⚫ |Section8={{Chembox Related
| OtherCompounds = ], ], ]
}} }}
⚫ | Section8 = {{Chembox Related
⚫ | OtherCpds = ]
⚫ }}
}} }}

'''Bis(2-chloroethyl)sulfide''' is the ] with the formula {{chem2|(ClCH2CH2)2S}}. It is a prominent member of a family of ] and ]s known as mustard agents. Sometimes referred to as '']'', the term is technically incorrect: bis(2-chloroethyl)sulfide is a liquid at room temperature. In warfare it was ] in the form of a fine mist of liquid droplets.<ref name="cdc">{{cite web|title=Sulfur Mustard: Blister Agent|language=en|website=]|date=25 May 2023 |access-date=2023-12-28|url=https://www.cdc.gov/niosh/ershdb/emergencyresponsecard_29750008.html|archive-url=http://web.archive.org/web/20231101235950/https://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750008.html|archive-date=2023-11-01}}</ref><ref>{{cite journal |doi=10.3109/10408444.2010.541224|title=Sulfur mustard toxicity: History, chemistry, pharmacokinetics, and pharmacodynamics |year=2011 |last1=Ghabili |first1=Kamyar |last2=Agutter |first2=Paul S. |last3=Ghanei |first3=Mostafa |last4=Ansarin |first4=Khalil |last5=Panahi |first5=Yunes |last6=Shoja |first6=Mohammadali M. |journal=Critical Reviews in Toxicology |volume=41 |issue=5 |pages=384–403 |pmid=21329486 |s2cid=28491672 }}</ref>

==Synthesis==
Bis(2-chloroethyl)sulfide has been prepared in a variety of ways. In the Depretz method, ] is treated with ]:
:{{chem2|SCl2 + 2 C2H4 -> (ClC2H4)2S}}

In the Levinstein process, ] is used instead:<ref name="Stewart, Charles D. 2006 47">{{Cite book|author=Stewart, Charles D. |title=Weapons of mass casualties and terrorism response handbook |publisher=Jones and Bartlett |location=Boston |year=2006 |page=47 |isbn=0-7637-2425-4 |url=https://books.google.com/books?id=7ZnXZfwWwgcC&q=levinstein+inventor+mustard&pg=PA46}}</ref>{{failed verification|date=September 2023}}<ref name="Federation of American Scientists">{{cite web|url=https://fas.org/programs/ssp/bio/chemweapons/production.html |title=Chemical Weapons Production and Storage |publisher=Federation of American Scientists |url-status=dead|archive-url=https://web.archive.org/web/20140811100809/http://fas.org/programs/ssp/bio/chemweapons/production.html |archive-date=August 11, 2014 }}</ref>
:{{chem2|S2Cl2 + 2 C2H4 -> (ClC2H4)2S}} + {{frac|1|8}} S<sub>8</sub>

In the Meyer method, ] is produced from ] and ], and the resulting ] is then treated with ]:<ref>{{cite journal |doi=10.15227/orgsyn.012.0068|title=β-Thiodiglycol |journal=Organic Syntheses |year=1932 |volume=12 |page=68|author=E. M. Faber and G. E. Miller }}</ref><ref>{{Cite book|url=http://books.nap.edu/openbook.php?record_id=2058&page=71|title=Chapter 5: Chemistry of Sulfur Mustard and Lewisite|author=Institute of Medicine |year=1993 |work=Veterans at Risk: The Health Effects of Mustard Gas and Lewisite |publisher=The National Academies Press |isbn=0-309-04832-X}}</ref>
:{{chem2|3 (HOC2H4)2S + 2 PCl3 -> 3 (ClC2H4)2S + 2 P(OH)3}}

In the Meyer&ndash;Clarke method, concentrated ] (HCl) is used instead of PCl<sub>3</sub>:
:{{chem2|(HOC2H4)2S + 2 HCl -> (ClC2H4)2S + 2 H2O}}

] and ], the latter of which is also a ], have also been used as chlorinating agents. These compounds have the added advantage in that if they are used in excess, they remain as impurities in the finished product and can therefore produce additional mechanisms of toxicity.

==Reactions==
The idealized combustion of mustard gas in oxygen produces ] and ], in addition to carbon dioxide and water:
:{{chem2|(ClC2H4)2S + 7 O2 -> 4 CO2 + 2 H2O + 2 HCl + H2SO4}}

Bis(2-chloroethyl)sulfide reacts with ], giving ]:
:{{chem2|(ClC2H4)2S + 2 NaOH -> (CH2\dCH)2S + 2 H2O + 2 NaCl}}
] acts similarly.

==Safety==
{{main|mustard gas}}
Upon skin contact or inhalation, bis(2-chloroethyl)sulfide is a nonspecific toxin. It is a strong ], which affects DNA, RNA, and proteins.<ref>{{cite journal |doi=10.1016/j.tox.2005.06.014|title=Medical aspects of sulphur mustard poisoning |year=2005 |last1=Kehe |first1=Kai |last2=Szinicz |first2=Ladislaus |journal=Toxicology |volume=214 |issue=3 |pages=198–209 |pmid=16084004 }}</ref>

==See also==
*]
*]
⚫ *]

==References==
{{Reflist}}

{{Chemical warfare}}
{{Sulfur mustards}}
{{U.S. chemical weapons}}

{{DEFAULTSORT:Mustard gas}}
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