Phenyl isothiocyanate acts as a derivatizing reagent for primary and secondary amines. It is used in sequencing peptides by Edman degradation and in amino acid analyses by HPLC. It is used for derivatizing N-terminal amino acids of proteins for automated sequential analysis. It is a synthon for dithiadiazafulvalenes.
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Applications
Phenyl isothiocyanate acts as a derivatizing reagent for primary and secondary amines. It is used in sequencing peptides by Edman degradation and in amino acid analyses by HPLC. It is used for derivatizing N-terminal amino acids of proteins for automated sequential analysis. It is a synthon for dithiadiazafulvalenes.
Solubility
Soluble in alcohol, and ether. Insoluble in water.
Notes
Moisture Sensitive. Protect from humidity and water. Store under dry inert gas away from oxidizing agents and moisture. Store at 4°C.
RUO – Research Use Only
General References:
- F Lai; T Sheehan. Matrix effects in the derivatization of amino acids with naphthalene dicarboxaldehyde, 9-fluorenylmethyl chloroformate and phenylisothiocyanate. BioTechniques.1993, 14 (4), 642-649.
- Mark C Wesley; Luis M Pereira; Laurie A Scharp; Sitaram M Emani; Francis X McGowan; James A DiNardo. Pharmacokinetics of tranexamic acid in neonates, infants, and children undergoing cardiac surgery with cardiopulmonary bypass. Anesthesiology.2015, 122 (4), 746-758.
- Derivatizing agent for amino groups. Introduced by Edman for the determination of amino acid sequence by conversion to the thiourea, acid cleavage of the peptide bond and alkaline hydrolysis of the derived thiohydantoin: Acta Chem. Scand., 4, 277 (1950); Arkiv. Kemi., 14, 291 (1959). The thiourea can also be cleaved with TFA: Nature, 227, 716 (1970), or by peracid oxidation: Chem. Ber., 89, 2288 (1956).
- For general reactions of isothiocyanates, see Appendix 3.