2,6-Xylidine

2,6-Xylidine
Names
	Preferred 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). 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, occurrence, 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]

2,6-Xylidine is also a major metabolite of the drug xylazine in both horses,^[2] and humans.^[3]

2,6-Xylidine is the precursor to the NHC ligand called Xyl.^[4]

Uses

2,6-Xylidine is a precursor to the fungicide metalaxyl^[5] and the herbicide metazachlor [de].^[6]

Synthesis of metazachlor

References

^ ^a ^b M. Meyer (2012). "Xylidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455. ISBN 9783527303854.
^ Spyridaki, M.-H.; Lyris, E.; Georgoulakis, I.; Kouretas, D.; Konstantinidou, M.; Georgakopoulos, C. G. (2004-04-01). "Determination of xylazine and its metabolites by GC-MS in equine urine for doping analysis". Journal of Pharmaceutical and Biomedical Analysis. 35 (1): 107–116. doi:10.1016/j.jpba.2003.12.007. ISSN 0731-7085. PMID 15030885 – via PubMed.
^ Drug & Chemical Evaluation Section (February 2021). Xylazine (PDF). Diversion Control Division (Report). Drug Enforcement Administration. DEA PRB # 2021-15. Retrieved 2022-11-15.
^ 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.
^ Blaser, Hans-Ulrich; Spindler, Felix (1997). "Enantioselective catalysis for agrochemicals. The case histories of (S)–metolachlor, (R)–metalaxyl and clozylacon". Topics in Catalysis. 4 (3/4): 275–282. doi:10.1023/A:1019164928084.
^ Unger, Thomas A. (1996-12-31). Pesticide Synthesis Handbook. William Andrew. p. 35. ISBN 0-8155-1853-6.

[Ullmann-1] M. Meyer (2012). "Xylidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455. ISBN 9783527303854.

[2] Spyridaki, M.-H.; Lyris, E.; Georgoulakis, I.; Kouretas, D.; Konstantinidou, M.; Georgakopoulos, C. G. (2004-04-01). "Determination of xylazine and its metabolites by GC-MS in equine urine for doping analysis". Journal of Pharmaceutical and Biomedical Analysis. 35 (1): 107–116. doi:10.1016/j.jpba.2003.12.007. ISSN 0731-7085. PMID 15030885 – via PubMed.

[3] Drug & Chemical Evaluation Section (February 2021). Xylazine (PDF). Diversion Control Division (Report). Drug Enforcement Administration. DEA PRB # 2021-15. Retrieved 2022-11-15.

[4] 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.

[5] Blaser, Hans-Ulrich; Spindler, Felix (1997). "Enantioselective catalysis for agrochemicals. The case histories of (S)–metolachlor, (R)–metalaxyl and clozylacon". Topics in Catalysis. 4 (3/4): 275–282. doi:10.1023/A:1019164928084.

[6] Unger, Thomas A. (1996-12-31). Pesticide Synthesis Handbook. William Andrew. p. 35. ISBN 0-8155-1853-6.

[1]

[2]

[3]

[4]

[5]

[6]

Names

Preferred IUPAC name 2,6-Dimethylaniline
Other names 2,6-Dimethylbenzene-1-amine 2,6-Dimethylbenzenamine 2,6-Dimethylphenylamine
Identifiers
CAS Number	87-62-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28738^Y
ChemSpider	6630^Y
ECHA InfoCard	100.001.599
KEGG	C11004^Y
PubChem CID	6896
UNII	4FT62OX08D^Y
CompTox Dashboard (EPA)	DTXSID8026307
InChI InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3^Y Key: UFFBMTHBGFGIHF-UHFFFAOYSA-N^Y 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 (n_D)	1.5601
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references