N-Phenylglycine

N-Phenylglycine
Names
	IUPAC name N-Phenylglycine
	Systematic IUPAC name 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;
PubChemCID	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	151.165g·mol−1
Appearance	white solid
Melting point	127–128 °C (261–262 °F; 400–401 K)
Hazards
	GHSlabelling:
Pictograms
Signal word	Warning
Hazard statements	H315,H319,H335
Precautionary statements	P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). Infobox references

N-Phenylglycineis anorganic compoundwith the formula C₆H₅NHCH₂CO₂H. This white solid achieved fame as the industrial precursor toindigo dye.^[1]It is anon-proteinogenic alpha amino acidrelated tosarcosine,but with anN-phenylgroup in place ofN-methyl.

Preparation[edit]

It is prepared by theStrecker reactioninvolving the reaction offormaldehyde,hydrogen cyanide,andaniline.The resulting amino nitrile is hydrolyzed to give the carboxylic acid.^[2]

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