para-Cresidine

*para*-Cresidine
Names


IUPAC name 2-methoxy-5-methylaniline
Identifiers
CAS Number	120-71-8^Y
3D model (Jmol)	Interactive image
ChemSpider	13869579^N
ECHA InfoCard	100.004.018
KEGG	C19216^Y
PubChem	8445
RTECS number	BZ6720000
InChI 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
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 [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

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.^[1]

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

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

References

1 2 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

International Chemical Safety Card, Center for Disease Control

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