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2,4-Xylidine

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2,4-Xylidine
Names
Preferred IUPAC name 2,4-Dimethylaniline
Other names 2,4-Dimethylphenylamine
2,4-Dimethylbenzenamine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 636243
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.219 Edit this at Wikidata
EC Number
  • 202-440-0
KEGG
PubChem CID
RTECS number
  • ZE8925000
UNII
UN number 1711
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H11N/c1-6-3-4-8(9)7(2)5-6/h3-5H,9H2,1-2H3Key: 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 GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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

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

References

  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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