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Names | |
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IUPAC name
N-Phenylglycine
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Systematic IUPAC name
Anilinoacetic acid | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.002.792 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
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: | |
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Warning | |
H315, H319, H335 | |
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).
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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
[edit]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]
![](https://upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Indigo_Synthesis_V.1.svg/400px-Indigo_Synthesis_V.1.svg.png)
See also
[edit]- Phenylglycine, an isomer with the formula C6H5CH(NH2)CO2H.
References
[edit]- ^ 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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