2,4-Xylidine

2,4-Xylidine
Names
	Preferred IUPAC name 2,4-Dimethylaniline
	Other names 2,4-Dimethylphenylamine; 2,4-Dimethylbenzenamine
Identifiers
CAS Number	95-68-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	636243
ChEBI	CHEBI:27840 ;
ChEMBL	ChEMBL1490826;
ChemSpider	6980 ;
ECHA InfoCard	100.002.219
EC Number	202-440-0;
KEGG	C11003;
PubChem CID	7250;
RTECS number	ZE8925000;
UNII	367R1L22C9 ;
UN number	1711
CompTox Dashboard (EPA)	DTXSID8026305 ;
	InChI InChI=1S/C8H11N/c1-6-3-4-8(9)7(2)5-6/h3-5H,9H2,1-2H3 Key: CZZZABOKJQXEBO-UHFFFAOYSA-N ;
	SMILES Cc1ccc(N)c(C)c1;
Properties
Chemical formula	C8H11N
Appearance	colourless liquid
Density	0.9763
Melting point	−15.9 °C (3.4 °F; 257.2 K)
Boiling point	218.0 °C (424.4 °F; 491.1 K)
Solubility in water	low
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H301, H311, H319, H330, H331, H373, H411
Precautionary statements	P260, P261, P264, P270, P271, P273, P280, P284, P301 P310, P302 P352, P304 P340, P305 P351 P338, P310, P311, P312, P314, P320, P321, P322, P330, P337 P313, P361, P363, P391, P403 P233, P405, P501
Flash point	100
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2,4-Xylidine is an organic compound with the formula C₆H₃(CH₃)₂NH₂. It is one of several isomeric xylidines. It is a colorless viscous liquid. Commercially significant derivatives include the veterinary drug cymiazole and the colorant Pigment Yellow 81.^[1]

Genotoxic and teratogenic, 2,4‑xylidine is an industrial pollutant.^[2] In addition, it is a degradant of the pesticide amitraz at very acidic pH values (<3).^[relevant?]^[3]

It is prepared by nitration of m-xylene followed by hydrogenation.

References

^ Meyer, M. (2012). "Xylidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455. ISBN 978-3527306732.
^ Brimecombe, R. D.; Fogel, R.; Limson, J. L. (2006). "Electrochemical monitoring of the biodegradation of 2,4-dimethylaniline". Journal of Agricultural and Food Chemistry. 54 (23): 8799–8803. doi:10.1021/jf061951k. PMID 17090125.
^ Corta, E. W.; Bakkali, A.; Berrueta, L. A.; Gallo, B.; Vicente, F. (1999). "Kinetics and mechanism of amitraz hydrolysis in aqueous media by HPLC and GC-MS". Talanta. 48 (1): 189–199. doi:10.1016/s0039-9140(98)00237-9. PMID 18967458.

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[1] Meyer, M. (2012). "Xylidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455. ISBN 978-3527306732.

[2] Brimecombe, R. D.; Fogel, R.; Limson, J. L. (2006). "Electrochemical monitoring of the biodegradation of 2,4-dimethylaniline". Journal of Agricultural and Food Chemistry. 54 (23): 8799–8803. doi:10.1021/jf061951k. PMID 17090125.

[3] Corta, E. W.; Bakkali, A.; Berrueta, L. A.; Gallo, B.; Vicente, F. (1999). "Kinetics and mechanism of amitraz hydrolysis in aqueous media by HPLC and GC-MS". Talanta. 48 (1): 189–199. doi:10.1016/s0039-9140(98)00237-9. PMID 18967458.

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