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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.
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.
Hazard Statements: H227-H301-H314-H318-H334-H317
Combustible liquid. Toxic if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause an allergic skin reaction.
Precautionary Statements: P210u-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.