N-Phenylglycine

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.

N-Phenylglycine

Names
IUPAC name 2-Anilinoacetic acid
Other names Anilinoacetic acid
Identifiers
CAS Number	103-01-5
3D model (JSmol)	Interactive image
ChemSpider	59416
ECHA InfoCard	100.002.792
EC Number	203-070-2
PubChem CID	66025
UNII	37YJW036TP
CompTox Dashboard (EPA)	DTXSID2047016
InChI InChI=1S/C8H9NO2/c10-8(11)6-9-7-4-2-1-3-5-7/h1-5,9H,6H2,(H,10,11) Key: NPKSPKHJBVJUKB-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)NCC(=O)O
Properties
Chemical formula	C8H9NO2
Molar mass	151.165 g·mol^−1
Appearance	white solid
Melting point	127–128 °C (261–262 °F; 400–401 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

Pfleger's historic synthesis of indigo using N-phenylglycine

See also

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

References

1. Helmut Schmidt (1997). "Indigo – 100 Jahre industrielle Synthese". Chemie in Unserer Zeit. 31 (3): 121–128. doi:10.1002/ciuz.19970310304.
2. Elmar Steingruber "Indigo and Indigo Colorants" Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a14_149.pub2