Xylylene dichloride

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]

Xylylene dichloride

1,2-, 1,3-, and 1,4-xylylene dichloride
Identifiers
3D model (JSmol)
ChemSpider
UNII
UN number 2928, 2811
  • 1,4: InChI=1S/C8H8Cl2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H,5-6H2
    Key: ZZHIDJWUJRKHGX-UHFFFAOYSA-N
  • 1,3: InChI=1S/C8H8Cl2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6H2
    Key: GRJWOKACBGZOKT-UHFFFAOYSA-N
  • 1,2: InChI=1S/C8H8Cl2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5-6H2
    Key: FMGGHNGKHRCJLL-UHFFFAOYSA-N
  • 1,4: C1=CC(=CC=C1CCl)CCl
  • 1,3: C1=CC(=CC(=C1)CCl)CCl
  • 1,2: C1=CC=C(C(=C1)CCl)CCl
Properties
C8H8Cl2
Molar mass 175.05 g·mol−1
Density 1.202
Melting point 34–37 °C (93–99 °F; 307–310 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H302, H314, H315, H317, H319, H330, H410
P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

References
  1. Xylylene dichloride. New Jersey Department of Health and Senior Services
  2. "XYLYLENE DICHLORIDE – National Library of Medicine HSDB Database". toxnet.nlm.nih.gov.
  3. Pubchem. "1,4-Bis(chloromethyl)benzene". pubchem.ncbi.nlm.nih.gov.
  4. Blinnikova, Z. K.; Golding, I. R.; Tsyurupa, M. P.; Fomkin, A. A.; Pulin, A. L.; Davankov, V. A. (1 January 2018). "Hypercrosslinked Polycondensation Networks: Copolymers of p-Xylylene Dichloride". Polymer Science, Series B. 60 (1): 91–98. doi:10.1134/S1560090418010013.
  5. "Hydroxyl Group Substitution". Chemistry LibreTexts. 2 October 2013.
  6. "1, 4-bis(chloromethyl)benzene synthesis technology" (2015) Chinese patent N105384595A
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