N-Phenylglycine Explained

N-Phenylglycine is an organic compound with the formula C₆H₅NHCH₂CO₂H. This white solid achieved fame as the industrial precursor to indigo dye.^[1] It is a non-proteinogenic alpha amino acid related to sarcosine, but with an N-phenyl group in place of N-methyl.

Preparation

It is prepared by the Strecker reaction involving the reaction of formaldehyde, hydrogen cyanide, and aniline. The resulting amino nitrile is hydrolyzed to give the carboxylic acid.^[2]

See also

• Phenylglycine, an isomer with the formula C₆H₅CH(NH₂)CO₂H.

References

1. Indigo – 100 Jahre industrielle Synthese. Chemie in unserer Zeit. Helmut Schmidt. 1997. 10.1002/ciuz.19970310304. 31. 3. 121–128.
2. Elmar Steingruber "Indigo and Indigo Colorants" Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim.