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;
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 labelling:
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 their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

Pfleger's historic synthesis of indigo using N-phenylglycine

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

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