Xylylene dichloride

Xylylene dichloride
	; 1,2-, 1,3-, and 1,4-xylylene dichloride
Identifiers
CAS Number	1,4: 623-25-6; 1,3: 626-16-4; 1,2: 612-12-4;
3D model (JSmol)	1,4: Interactive image; 1,3: Interactive image; 1,2: Interactive image;
ChemSpider	1,4: 11671; 1,3: 21168838; 1,2: 21111896;
PubChem CID	1,4: 12171; 1,3: 12275; 1,2: 11919;
UNII	1,4: 55E5A3M473;
UN number	2928, 2811
	InChI 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;
	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−1
Density	1.202
Melting point	34–37 °C (93–99 °F; 307–310 K)
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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.

References

^ Xylylene dichloride. New Jersey Department of Health and Senior Services
^ ^a ^b "XYLYLENE DICHLORIDE – National Library of Medicine HSDB Database". toxnet.nlm.nih.gov.
^ ^a ^b Pubchem. "1,4-Bis(chloromethyl)benzene". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ "Hydroxyl Group Substitution". Chemistry LibreTexts. 2 October 2013.
^ "1, 4-bis(chloromethyl)benzene synthesis technology" (2015) Chinese patent N105384595A

[1] Xylylene dichloride. New Jersey Department of Health and Senior Services

[r9-2] "XYLYLENE DICHLORIDE – National Library of Medicine HSDB Database". toxnet.nlm.nih.gov.

[r1-3] 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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