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para-Cresidine

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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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.018 Edit this at Wikidata
KEGG
PubChem CID
RTECS number
  • BZ6720000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H11NO/c1-6-3-4-8(10-2)7(9)5-6/h3-5H,9H2,1-2H3Key: WXWCDTXEKCVRRO-UHFFFAOYSA-N
  • InChI=1/C8H11NO/c1-6-3-4-8(10-2)7(9)5-6/h3-5H,9H2,1-2H3Key: WXWCDTXEKCVRRO-UHFFFAOYAY
SMILES
  • CC1=CC(=C(C=C1)OC)N
Properties
Chemical formula 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

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.

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

External links

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