— 83 — 



the presence of n-butyl mustard oil (b. p. 167°) or secondary-butyl mustard 

 oil (b. p. 159,5°) afforded any reason for assuming the existence in them 

 of the bodies in question. 



Allyl isothiocyanate, or ally 1 mustard oil, CH 2 : CHCH 2 NCS. 

 This formed the principal portion of the fractions boiling between 150 

 and 163°. A fraction passing over between 155 and 157° was found to 

 possess the following constants: duo 1,0181, n D20 o 1,52458. Combustion 

 of the oil and of the thio-urea or thiosinamine CH 2 : CHCH 2 -NHCSNH 2 , 

 m. p. 12 to 73°, gave the following values: — 



Oil. 0,1562 g. subst: 0,2772 g. C0 2 , 0,0773 g. H 2 0. 



Found Calc. for C 4 H 5 NS 



C 48,40 % 48,48 °/o 



H 4,95 % 5,05 °/o. 



Thio-urea. 0,1696 g. subst: 0,2594 g. C0 2 , 0,1079 g. H 2 0. 



Found Calc. for C 4 H 8 N 2 S 



C 41,71% 41,38% 



H 7,07 % 6,89 °/o. 



The proportion of allyl isothiocyanate in the oil is probably scarcely 

 more than 40°/ . 



Crotonyl mustard oil, C 4 H 7 NCS. Examination of the fractions 

 with the highest boiling points showed them to consist of a uniform body; 

 the analyses pointing to a crotonyl mustard oil with the formula C 4 H 7 NCS. 

 A medium fraction with the b. p. 175 to 176° was found to possess the 

 following physical constants: d i5 o 0,9941, « D + 0°3', n D20 o 1,52398. 

 0,1793 g. subst.: 0,3489 g. C0 2 , 0,0981 g. H 2 0. 

 0,1761 g. subst.: 0,3631 g. BaS0 4 . 



Found Calc. for C 5 H 7 NS 



C 53,07 °/o 53,09% 



H 6,08 °/o 6,19°/o 



S 28,32°/o 28,32°/o. 



The thio-urea C 4 H 7 NHCS-NH 2 of the above fraction occurs in long 

 needles, clearly distinguishable in external appearance, from the stout 

 glittering prisms of thiosinamine. Purified from chloroform and light 

 petroleum the thio-urea melts at 69 to 70°. 



1. 0,1759 g. subst.: 0,2983 g. C0 2 , 0,1256 g. H 2 0. 



2. 0,1701 g. subst.: 0,2881 g. C0 2 , 0,1191 g. H 2 0. 



3. 0,2098 g. subst.: 0,3745 g. BaS0 4 . 



Calc. for C 5 H 10 N 2 S 



3. 



46,15% 



7,69% 



24,51% 24,62 °/o. 



6* 





Found 



1. 



2. 



C 46,25% 



46,19% 



H 7,93% 



7,77% 



S — 



— 



