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Xylylene dichloride

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Xylylene dichloride

1,2-, 1,3-, and 1,4-xylylene dichloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
UN number 2928, 2811
InChI
  • 1,4: InChI=1S/C8H8Cl2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H,5-6H2Key: ZZHIDJWUJRKHGX-UHFFFAOYSA-N
  • 1,3: InChI=1S/C8H8Cl2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6H2Key: GRJWOKACBGZOKT-UHFFFAOYSA-N
  • 1,2: InChI=1S/C8H8Cl2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5-6H2Key: FMGGHNGKHRCJLL-UHFFFAOYSA-N
SMILES
  • 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
Chemical formula C8H8Cl2
Molar mass 175.05 g·mol
Density 1.202
Melting point 34–37 °C (93–99 °F; 307–310 K)
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Signal word Danger
Hazard statements H302, H314, H315, H317, H319, H330, H410
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

The chemical compound xylylene dichloride (C6H4(CH2Cl)2) is a white to light yellow sandlike solid. This compound can be classified as a benzyl halide. 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. 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. It has also been produced by photochemical chlorination of ortho-xylene.

Related compounds

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. S2CID 258701237.
  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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