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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