Phenyl mustard oil

Heat gently 0 5 c.c. phenyl mustard oil, and o 5 c.c. aniline on cooling and rubbing with a gdass rod, thiocarbanilidc crystallises. 

Heat on the water-bath in a small flask with upright condenser 3 grams of phenyl mustard oil and 10 c.c. absolute alcohcrl for 3 hours, and pour into cold water. Phenylthioureth tine, C jHjNH.CS.OC Hj, separates out and may be recrystallised from alcohol. Yield, 25 grams m. p. 67 . 

Triphenylguanidine.—In order to separate the triphenylguanidine leinaining in the flask as hydrochlorideaftci distilling off the phenyl mustard oil, the hot solution must be somewhat concentiated. The colourless salt, which crystallises out on cool-... 

Among the reactions appended to this preparation, the foi-mation of phenylcaibiniide from phenyl mustard oil is desciibetl. It should be noted that phenyl carbimide, like the thiocarbiniide, unites with ammonia, amines, and more especially with alcohols and phenols. The bases yield urea derivatives the alcohols and phenols foim urethanes. 

Phenyl-jodidchlorid, n. phenyl iodochloride, -milchsaure, /. phenyllactic acid, -saure, /. phenylic acid (phenol, CeHaOH). -schwefel-saure, /. phenylsulfuric acid, -senfol, n. phenyl mustard oil. -siliciumchlorid, n. trichlorophenylsilane, CaHiSiCla. -verbindung, /. phenyl compound, -wasserstoff, m. phenyl hydride, benzene. 

The dearrangement of phenylthiourea may be demonstrated very simply by heating a small quantity of the material in a test-tube. It undergoes a violent decomposition slightly above its melting-point, the odors of ammonia, of aniline, and of phenyl mustard oil may be detected, and the residue which consists largely of sym.-diphenylthiourea gives with ferric chloride the a ed color characteristic of thiocyanic acid. 

Niirothiocarbanilide, ndls or yel scales, mp 155° 160° sol in warm ale si sol in benz, chlf, carbon disulfide cold ale. It can be prepd by heating 3-nitroaniline phenyl mustard oil, CeHjNiCS (Refs 2, 3 4) N-PhenyI-N/ (4-nitropbenyl)-tbiourea or... 

Phenylisothiocyanate (phenyl mustard oil) [103-72-0] M 135.2, m -21 , b 95 /12mm, 117.1 /33mm, 221 /760mm, d 1.1288, n 1.64918. It is insol in H2O, but sol in Et2O and EtOH. If impure (due to formation of thiourea) then steam dist into a receiver containing 5-lOml of N H2SO4. Separate the oil, dry over CaCl2 and distil under vacuum. [Dains et al. Org Synth Coll Vol I 447 1941. ... 

Also termed phenyl mustard oil or phenyl tliiocarbimide. 

Towards light, carbon disulphide possesses high refractive and dispersive powers, and in these properties is exceeded only by methylene iodide, bromonaphthalene and phenyl mustard oil. On this account it is used for filling hollow glass prisms for the production of spectra.4... 

Yield.—50% theoretical (3 gms.). Colourless, mobile liquid characteristic odour B.P. 135° D. w4 e 0-9755 gives a cherry-red colour with a solution of isatin in cone, sulphuric acid. (B., 18, 2251 20,1747.) Preparation 433.—PhenyKsothiocyanate (Phenyl mustard oil). 

Upon heating the diarylthiourea with concentrated hydrochloric acid, it is partly converted into the aryl isothiocyanate (e.g. phenyl isothiocyanate or phenyl mustard oil, Expt 6.98, Method 1). A little hydrogen sulphide is evolved in a side reaction forming diphenylcarbodi-imide (4) which undergoes nucleophilic addition of aniline to yield triphenylguanidine (5), isolated from the reaction mixture as the hydrochloride. 

PHENYL MUSTARD OIL PHENYLSENFOEL (GERM-tN) PITC THIOCARBANIL USAF M-4... 

PHENYL MUSTARD OIL see ISQOOO PHENYL-2-NAPHTHYLAMINE see PFT500 N-PHENYL-2-NAPHTHYLAXnNE see PFT500... 

Hatschek, who concluded that viscosity can give some useful indication of compound formation. A mixture of stannic chloride (SnC ) and acetic acid has a very sharp maximum for equimolar amounts, and pronounced maxima are also found with mixtures of allyl and phenyl mustard oils with methylaniline and diethylamine, respectively. ... 

Phcnylcarbyinmine chloride is produced by chlorinating phenyl mustard oil (C HjKCS), derivM from I lie action of carbon disulfide on aniline. The product Is a tran.spurent liquid, of 1.3o specific gravity, which IxiiLs at (410" .), yielding a vapor 6.0 times heavier than air. 

Example Thiocarbanllide and Phenyl Mustard Oil from Carbon Disulphide and Aniline... 

Phenyl Mustard Oil 1 In a flask of about 400 c.c. capacity place 30 grammes of the crude thiocarbanilide, and treat with 120 grammes of concentrated hydrochloric acid the mixture is distilled by heating to the boiling-point of the acid, on a sand-bath, with a large flame under a hood. When only about 20 c.c. of the liquid remain in the flask, the distillation is discontinued. The distillate is treated with an equal volume of water, the mustard... 

Experiment Treat 2 drops of phenyl mustard oil on a watch-glass with 2 drops of aniline, and warm gently over a small flame. On stirring the reaction-product after cooling, with a glass rod, the thiocarbanilide will solidify in crystals, from which in the above reverse reaction the mustard oil itself was prepared. 

Experiment Heat c.c. of phenyl mustard oil in a test-tube with the same volume of yellow mercuric oxide for some time, until the oil boils. The yellow oxide is changed to the black sulphide, at the same time the extremely disagreeable odour of the phenyl isocyanate arises the vapour of the compound attacks the eyes, causing tears. 

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