para-Cresidine

para-Cresidine is an organic compound with the formula CH3OC6H3(CH3)NH2. It is a white solid that is soluble in organic solvents. The compound features both amine and methoxy functional groups. It is used as an intermediate in preparation of dyes and pigments.

para-Cresidine
Skeletal formula of para-cresidine
Ball-and-stick model of the para-cresidine molecule
Names
Preferred IUPAC name
2-Methoxy-5-methylaniline
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.018
KEGG
RTECS number
  • BZ6720000
UNII
  • InChI=1S/C8H11NO/c1-6-3-4-8(10-2)7(9)5-6/h3-5H,9H2,1-2H3 ☒N
    Key: WXWCDTXEKCVRRO-UHFFFAOYSA-N ☒N
  • InChI=1/C8H11NO/c1-6-3-4-8(10-2)7(9)5-6/h3-5H,9H2,1-2H3
    Key: WXWCDTXEKCVRRO-UHFFFAOYAY
  • CC1=CC(=C(C=C1)OC)N
Properties
C8H11NO
Molar mass 137.179
Appearance White crystals
Melting point 51.5 °C (124.7 °F; 324.6 K)
Boiling point 235 °C (455 °F; 508 K)
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

Synthesis and reactions

The compound is obtained in several steps from 4-chlorotoluene. Nitration gives mainly 3-nitro-4-chlorotoluene, which reacts with methoxide sources to give 4-methoxy-2-nitrotoluene. Reduction of this nitro compound affords the aniline.[1]

Sulfonation with oleum gives 4-amino-5-methoxy-2-methylbenzenesulfonic acid. This sulfonic acid is a precursor to allura red AC, a red food coloring.[1]

Allura Red AC is a popular food coloring agent made from para-cresidine.

References
  1. P. F. Vogt, J. J. Gerulis, "Amines, Aromatic" in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_037
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