xylylene dichloride
{{Chembox
| ImageFile = Xylylene dichlorides.svg
| ImageSize = 250px
| ImageCaption = 1,2-, 1,3-, and 1,4-xylylene dichloride
|Section1 = {{Chembox Identifiers
| index1_label=1,4
| index2_label=1,3
| index3_label=1,2
| CASNo1 = 623-25-6
| CASNo2 = 626-16-4
| CASNo3 = 612-12-4
| UNNumber = 2928, 2811
| UNII1 = 55E5A3M473
| PubChem1=12171
| PubChem2=12275
| PubChem3=11919
| ChemSpiderID1 = 11671
| ChemSpiderID2 = 21168838
| ChemSpiderID3 = 21111896
| InChI1=1S/C8H8Cl2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H,5-6H2
| InChIKey1 = ZZHIDJWUJRKHGX-UHFFFAOYSA-N
| InChI2=1S/C8H8Cl2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6H2
| InChIKey2 = GRJWOKACBGZOKT-UHFFFAOYSA-N
| InChI3=1S/C8H8Cl2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5-6H2
| InChIKey3 = FMGGHNGKHRCJLL-UHFFFAOYSA-N
| SMILES2 = C1=CC(=CC(=C1)CCl)CCl
| SMILES1 = C1=CC(=CC=C1CCl)CCl
| SMILES3 = C1=CC=C(C(=C1)CCl)CCl
}}
|Section2 = {{Chembox Properties
|C=8|H=8|Cl=2
| MeltingPtC = 34–37
| Density = 1.202
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|302|314|315|317|319|330|410}}
| PPhrases = {{P-phrases|260|261|264|270|271|272|273|280|284|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|320|321|330|332+313|333+313|337+313|362|363|391|403+233|405|501}}
}}
}}
The chemical compound xylylene dichloride (C6H4(CH2Cl)2) is a white to light yellow sandlike solid.[https://nj.gov/health/eoh/rtkweb/documents/fs/2858.pdf Xylylene dichloride]. New Jersey Department of Health and Senior Services This compound can be classified as a benzyl halide.{{cite web|url=https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+6349|title=XYLYLENE DICHLORIDE – National Library of Medicine HSDB Database|website=toxnet.nlm.nih.gov}}{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/12171|title=1,4-Bis(chloromethyl)benzene|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov}} Xylylene dichloride is used as a vulcanizing agent to harden rubbers. It catalyzes the crosslinking of phenolic resins.
Structure and reactivity
The structure of xylylene dichloride is characterized by an benzene ring with two chloromethyl groups and four hydrogen atoms bound to it.{{cite journal|title=Hypercrosslinked Polycondensation Networks: Copolymers of p-Xylylene Dichloride|first1=Z. K.|last1=Blinnikova|first2=I. R.|last2=Golding|first3=M. P.|last3=Tsyurupa|first4=A. A.|last4=Fomkin|first5=A. L.|last5=Pulin|first6=V. A.|last6=Davankov|date=1 January 2018|journal=Polymer Science, Series B|volume=60|issue=1|pages=91–98|doi=10.1134/S1560090418010013|s2cid=258701237 }} The chloromethyl groups can be located on different sites on the ring, leading to a few different possible forms. These forms are:
- o-xylylene dichloride: 1,2-bis(chloromethyl)benzene
- m-xylylene dichloride: 1,3-bis(chloromethyl)benzene
- p-xylylene dichloride: 1,4-bis(chloromethyl)benzene
The reactive groups of xylylene dichloride are the two CH2Cl groups.
Synthesis
Xylylene dichloride can be synthesized from benzenedimethanol by reaction with hydrogen chloride.{{cite web|url=https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Alcohols/Reactivity_of_Alcohols/Hydroxyl_Group_Substitution|title=Hydroxyl Group Substitution|date=2 October 2013|website=Chemistry LibreTexts}} It has also been produced by photochemical chlorination of ortho-xylene."1, 4-bis(chloromethyl)benzene synthesis technology" (2015) [https://patents.google.com/patent/CN105384595A/en Chinese patent N105384595A]
Related compounds
- Xylylene dibromide, the dibromo analogue of the title compound.