2,6-Xylidine

2,6-Xylidine
Names
	IUPAC name 2,6-Dimethylaniline
	Other names 2,6-Dimethylbenzene-1-amine; 2,6-Dimethylbenzenamine; 2,6-Dimethylphenylamine;
Identifiers
CAS Number	87-62-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28738 ;
ChemSpider	6630 ;
ECHA InfoCard	100.001.599
KEGG	C11004 ;
PubChem CID	6896;
UNII	4FT62OX08D ;
CompTox Dashboard (EPA)	DTXSID8026307 ;
	InChI InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3 Key: UFFBMTHBGFGIHF-UHFFFAOYSA-N ; InChI=1/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3 Key: UFFBMTHBGFGIHF-UHFFFAOYAI;
	SMILES Nc1c(cccc1C)C;
Properties
Chemical formula	C8H11N
Molar mass	121.183 g·mol−1
Appearance	Colorless liquid
Density	0.9842 g/mL
Melting point	11.45 °C (52.61 °F; 284.60 K)
Boiling point	215 °C (419 °F; 488 K)
Refractive index (nD)	1.5601
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

2,6-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 are the anesthetics lidocaine, bupivacaine, mepivacaine, and etidocaine.[1]

Production and reactions

Many xylidines are prepared by nitration of a xylene followed by hydrogenation of the nitroaromatic, but this approach is not efficient for this isomer. Instead, it is prepared from by treatment of the related xylenol with ammonia in the presence of oxide catalysts.[1]

Other

2,6-Xylidine is the precursor to the NHC ligand IXyl.[2]

References

M. Meyer (2012). "Xylidines". Ullmann's Encylclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455.
Ison, Elon A.; Ison, Ana (2012). "Synthesis of Well-Defined CopperN-Heterocyclic Carbene Complexes and Their Use as Catalysts for a "Click Reaction": A Multistep Experiment That Emphasizes the Role of Catalysis in Green Chemistry". Journal of Chemical Education. 89 (12): 1575. Bibcode:2012JChEd..89.1575I. doi:10.1021/ed300243s.

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

[2] Ison, Elon A.; Ison, Ana (2012). "Synthesis of Well-Defined CopperN-Heterocyclic Carbene Complexes and Their Use as Catalysts for a "Click Reaction": A Multistep Experiment That Emphasizes the Role of Catalysis in Green Chemistry". Journal of Chemical Education. 89 (12): 1575. Bibcode:2012JChEd..89.1575I. doi:10.1021/ed300243s.