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1,1-Bis(chloromethyl)ethylene

{{Chembox

|ImageFile = CH2C(CH2Cl)2.png

|ImageSize = 124

|PIN = 3-Chloro-2-(chloromethyl)prop-1-ene

|OtherNames = 3-Chloro-2-(chloromethyl)propene, 1,1-Bis(chloromethyl)ethene

|Section1={{Chembox Identifiers

|CASNo = 1871-57-4

|PubChem = 15859

|StdInChI=1S/C4H6Cl2/c1-4(2-5)3-6/h1-3H2

|StdInChIKey = XJFZOSUFGSANIF-UHFFFAOYSA-N

|SMILES = C=C(CCl)CCl

|EINECS = 217-489-3

|UNII = 1XTP1GFW2A

|ChEMBL = 160833

|ChemSpiderID = 15073

}}

|Section2={{Chembox Properties

|C=4|H=6|Cl=2

|Appearance = Colorless liquid

|Density = 1.1782 g/cm3

|MeltingPtC = -14

|MeltingPt_ref = {{cite journal |last1=Mooradian |first1=Aram |last2=Cloke |first2=J. B. |title=The Synthesis of 3-Chloro-2-chloromethyl-1-propene from Pentaerythritol |journal=Journal of the American Chemical Society |date=June 1945 |volume=67 |issue=6 |pages=942–944 |doi=10.1021/ja01222a019}}

|BoilingPtC = 138

|BoilingPt_ref =

}}

|Section3={{Chembox Hazards

|GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS09}}

|GHSSignalWord = danger

|HPhrases = {{H-phrases|226|301|315|319|335|400}}

|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|273|280|301+310|302+352|303+361+353|304+340|305+351+338|312|321|330|332+313|337+313|362|370+378|391|403+233|403+235|405|501}}

|MainHazards = alkylating agent

}}

}}

1,1-Bis(chloromethyl)ethylene is the organic compound with the formula CH2=C(CH2Cl)2. It is a colorless liquid. Featuring two allylic chloride substituents, it is dialkylating agent.

Synthesis and reactions

It is prepared from pentaerythritol via a multistep procedure, beginning with the partial chlorination.{{cite journal|title=Improved Preparations of 3-Chloro-2-(chloromethyl)-1-propene and 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane: Intermediates in the Synthesis of [1.1.1]Propellane|last1=Mondanaro Lynch|first1=Kathleen|last2=Dailey|first2=William P.|journal=Journal of Organic Chemistry|year=1995|volume=60|issue=14 |page=4666-8|doi=10.1021/jo00119a057}}{{cite journal |last1=Mondanaro |first1=Kathleen R. |last2=Dailey |first2=William P |title=3-CHLORO-2-(CHLOROMETHYL)-1-PROPENE |journal=Organic Syntheses |date=1998 |volume=75 |pages=89 |doi=10.15227/orgsyn.075.0089}}{{open access}} The compound reacts with diiron nonacarbonyl to give the complex of trimethylenemethane Fe(η4-C(CH2)3)(CO)3. It is also a precursor to [1.1.1]-propellane.

References

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Category:Chloroalkenes

Category:Vinylidene compounds