Xylylene dichloride explained

The chemical compound xylylene dichloride (C₆H₄(CH₂Cl)₂) is a white to light yellow sandlike solid.^[1] This compound can be classified as a benzyl halide.^{[2] [3]} Xylylene dichloride is used as a vulcanizing agent to harden rubbers. It catalyzes the crosslinking of phenolic resins.^[2]

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.^[4] The chloromethyl groups can be located on different sites on the ring, leading to a few different possible forms. These forms are:^[3]

• 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.^[5] It has also been produced by photochemical chlorination of ortho-xylene.^[6]

Related compounds

• Xylylene dibromide, the dibromo analogue of the title compound.

Notes and References

1. https://nj.gov/health/eoh/rtkweb/documents/fs/2858.pdf Xylylene dichloride
2. Web site: XYLYLENE DICHLORIDE – National Library of Medicine HSDB Database. toxnet.nlm.nih.gov.
3. Web site: 1,4-Bis(chloromethyl)benzene. Pubchem. pubchem.ncbi.nlm.nih.gov.
4. Hypercrosslinked Polycondensation Networks: Copolymers of p-Xylylene Dichloride. Z. K.. Blinnikova. I. R.. Golding. M. P.. Tsyurupa. A. A.. Fomkin. A. L.. Pulin. V. A.. Davankov. 1 January 2018. Polymer Science, Series B. 60. 1. 91–98. 10.1134/S1560090418010013. 258701237 .
5. Web site: Hydroxyl Group Substitution. 2 October 2013. Chemistry LibreTexts.
6. "1, 4-bis(chloromethyl)benzene synthesis technology" (2015) Chinese patent N105384595A