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Revision as of 16:29, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443256172 of page 1,4-Dichlorobut-2-ene for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 22:37, 25 August 2024 edit Bernanke's Crossbow (talk | contribs)Extended confirmed users7,863 editsm →top: typo fix 
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{{short description|Chemical compound}}
{{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
⚫ | verifiedrevid = 443254880
| Watchedfields = changed
⚫ | ImageFile=1,4-Dichlorobut-2-ene.svg
⚫ | verifiedrevid = 477206209
⚫ | Section1 = {{Chembox Identifiers
| ImageFile=trans-1,4-Dichlorobutene.svg
⚫ | InChI = 1/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+
| ImageFile1 = 1,4-Dichlorobut-2-ene-3D-balls.png
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| ImageAlt1 = 1,4-Dichlorobut-2-ene molecule
⚫ | IUPACName = 1,4-Dichlorobut-2-ene
| OtherNames = ''trans''-1,4-Dichlorobutene
⚫ |Section1={{Chembox Identifiers
⚫ | InChI = 1/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2 | StdInChI = 1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2
| InChIKey = FQDIANVAWVHZIR-OWOJBTEDBY | InChIKey = FQDIANVAWVHZIR-OWOJBTEDBY
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FQDIANVAWVHZIR-UHFFFAOYSA-N | StdInChIKey = FQDIANVAWVHZIR-UHFFFAOYSA-N
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14394 | ChemSpiderID = 557415
| SMILES = ClC/C=C/CCl | SMILES = ClC/C=C/CCl
| InChI1 = 1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2 | InChI1 = 1S/C4H6Cl2/c5-3-1-2-4-6/h1-2H,3-4H2
| InChIKey1 = FQDIANVAWVHZIR-UHFFFAOYSA-N | InChIKey1 = FQDIANVAWVHZIR-UHFFFAOYSA-N
| SMILES1 = ClCC=CCCl | SMILES1 = ClCC=CCCl
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 110-57-6 -->
| CASNo_Comment = <!-- CASRN verified at ESIS and NIST --> | CASNo = 110-57-6
| CASNo_Comment = <!-- CASRN verified at ESIS and NIST -->
| EC-number = 203-779-7 | EC_number = 203-779-7
| PubChem = 642197
| UNNumber = 2920 2927 2922
| UNII = 92HZ946H7Y
| ChEBI = 82446
| KEGG = C19398
| ChEMBL = 468582
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=4 | H=6 | Cl=2
| Formula = C<sub>4</sub>H<sub>6</sub>Cl<sub>2</sub>
| MolarMass = 125.00 g/mol | Density = 1.13 g/mL
| MeltingPtC = 1
| BoilingPtC = 125.5
| Appearance = Colorless liquid
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| Reference = <ref>Index no.&nbsp;602-073-00-X of Annex&nbsp;VI, Part&nbsp;3, to . ''OJEU'' L353, 31.12.2008, pp&nbsp;1–1355 at p&nbsp;473.</ref> | Hazards_ref = <ref>Index no.&nbsp;602-073-00-X of Annex&nbsp;VI, Part&nbsp;3, to . ''OJEU'' L353, 31.12.2008, pp&nbsp;1–1355 at p&nbsp;473.</ref>
⚫ | GHSPictograms = {{GHS skull and crossbones}} {{GHS health hazard}}<br/>{{GHS corrosion}} {{GHS environment}}
| EUIndex = 602-073-00-X<!--
⚫ | GHSSignalWord = DANGER
| EUClass = Carc. Cat. 2<br/>Very toxic ('''T+''')<br/>Corrosive ('''C''')<br/>Dangerous for the environment ('''N''')
⚫ | HPhrases = {{H-phrases|350|330|311|301|314|410}}
| RPhrases = R45, R24/25, R26, R34, R50/53
| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|264|270|271|273|280|281|284|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|307+311|308+313|310|312|314|320|321|322|330|361|363|370+378|391|403+233|403+235|405|501}}
| SPhrases = S53, S45, S60, S61-->
⚫ | GHSPictograms = {{GHS skull and crossbones}}{{GHS health hazard}}<br/>{{GHS corrosion}}{{GHS environment}}
⚫ | GHSSignalWord = DANGER
⚫ | HPhrases = {{H-phrases|350|330|311|301|314|410}}
| PPhrases =
}} }}
}} }}

'''1,4-Dichlorobut-2-ene''' are ]s with the formula {{chem2|ClCH2CH\dCHCH2Cl}}. Cis and trans isomers exist. These compounds are intermediates in the industrial production of ]. They are main impurity in technical grade chloroprene.<ref>{{citation | pages = 227–50 | url = http://monographs.iarc.fr/ENG/Monographs/vol71/mono71-9.pdf | series = IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 71 | publisher = International Agency for Research on Cancer | location = Lyon, France | title = Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide | year = 1999 | isbn = 92-832-1271-1}}.</ref>

==Production of chloroprene==
Chloroprene is a monomer for the production of ]s such as ]. It is produced from ] in a three-step process. The first step is the liquid- or vapour-phase chlorination of butadiene to a mixture of ] and 1,4-dichlorobut-2-ene (both isomers). In the second step, the mixture of 1,4-dichlorobut-2-ene and 3,4-dichlorobut-1-ene is isomerized to 3,4-dichlorobut-1-ene by heating to temperatures of 60–120&nbsp;°C in the presence of a catalyst. Finally, ] (] of ]) of 3,4-dichlorobut-1-ene with dilute ] solution in the presence of ]s gives crude chloroprene.<ref>{{citation | last = Kleinschmidt | first = P. | year = 1986 | contribution = Chlorinated hydrocarbons. 6.4. 2-Chloro-1,3-butadiene | editor1-last = Gerhartz | editor1-first = W. | editor2-last = Yamamoto | editor2-first = Y. S. | title = Ullmann's Encyclopedia of Industrial Chemistry | edition = 5th | volume = A6 | location = Weinheim | publisher = VCH | pages = 315–18}}<br />{{citation | last = Stewart | first = C. A. Jr. | year = 1993 | contribution = Chlorocarbons, -hydrocarbons (chloroprene) | editor1-last = Kroschwitz | editor1-first = J. I. | editor2-last = Howe-Grant | editor2-first = M. | title = Kirk-Othmer Encyclopedia of Chemical Technology | edition = 4th | volume = 6 | location = New York | publisher = John Wiley | pages = 70–78}}.</ref>

==Other reactions==
1,4-Dichlorobut-2-ene is a precursor to various heterocycles.<ref>{{cite journal |doi=10.15227/orgsyn.073.0246 |author=Albert I. Meyers, Joseph S. Warmus, Garrett J. Dilley|title=3-Pyrroline |journal=Organic Syntheses |date=1996 |volume=73 |page=246 }}</ref>

The (''E'')-isomer is also one of the starting materials for the ] natural product ].<ref name="sceptrin">{{citation | last1 = Birman | first1 = Vladimir B. | last2 = Jiang | first2 = Xun-Tian | title = Synthesis of Sceptrin Alkaloids | journal = Org. Lett. | year = 2004 | volume = 6 | issue = 14 | pages = 2369–71 | doi=10.1021/ol049283g | pmid = 15228281}}. {{citation | last1 = Baran | first1 = Phil S. | last2 = Zografos | first2 = Alexandros L. | last3 = O'Malley | first3 = Daniel P. | author-link1 = Phil S. Baran | title = Short Total Synthesis of (±)-Sceptrin | journal = J. Am. Chem. Soc. | year = 2004 | volume = 126 | issue = 12 | pages = 3726–27 | doi=10.1021/ja049648s | pmid = 15038721}}.</ref>

==References==
{{reflist}}

{{DEFAULTSORT:Dichlorobutene-2, 1, 4-}}
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