Phenyl isothiocyanate

• Isothiocyanatobenzol (IUPAC)
• Phenylsenföl
• Thiocarbanil
• Edman reagent

1.13 g · cm -3

-21 ° C.

221 ° C

10 mbar (20 ° C)

Decomposition in water

1.6492 (23 ° C)

Risk

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Phenyl isothiocyanate ( PITC ) is a chemical compound useful as a reagent for chemical analysis ( Edman reagent) and synthetic organic chemistry will be used. The other name Phenylsenföl is on the relationship with the carrier taste the mustard, the allyl isothiocyanate ( CH2 = CH- CH 2 N = C = S) due.

Representation

Aniline reacts with carbon disulfide in ethanol and finely divided potassium hydroxide as a catalyst to diphenylthiourea. This reaction is believed to proceed via the intermediate products Phenyldithiocarbaminsäure and phenyl isothiocyanate with elimination of hydrogen sulfide. From the diphenylthiourea formed step in the action of acids with elimination of aniline phenyl isothiocyanate is formed in the next:

Another method for the preparation of phenyl is also of aniline and carbon disulfide in concentrated ammonium hydroxide solution. The isolated as an intermediate salt Ammoniumphenyldithiocarbamat is transferred with lead nitrate in phenyl isothiocyanate:

Properties

Phenyl isocyanate is a colorless to yellowish liquid with acrid, senfartigem odor that irritates the eyes to tears. At atmospheric pressure, the compound at 221 ° C. The boiling vapor pressure function is given by Antoine accordingly

In the temperature range of 320 K to 491 K.

The compound reacts violently with alcohols, amines, acids, bases, water and oxidizing agents.

Use

It is used as the eluent in the reverse-phase high performance liquid chromatography for analysis of the secondary amines used in the synthesis and chemistry as the reagent in the Edman degradation and, therefore, referred to as " Edman reagent".