40 
CJ dor  acetones. 
Am  Jour.  Pharm. 
Jan.,18S8. 
and  at  190°  under  the  ordinary  pressure.  It  is  very  hygroscopic,  and 
forms  a  tetrahydrate  which  crystallizes  in  hexagonal  tables  melting  at 
48°.  With  ammonia,  it  yields  chloroform  and  bromacetamide,  and 
therefore  must  have  the  constitution  CCl3*CO-CH2Br. 
Tetrabromacetone  forms  a  tetrahydrate,  which,  although  unstable, 
crystallizes  readily.  With  ammonia,  it  yields  bromoform  and  brom- 
acetamide. 
All  the  chlorobromacetones  described  are  tetra-substitution-deriva- 
tives.  Starting  from  tetrachloracetone,  each  substitution  of  bromine 
for  chlorine  produces  a  rise  of  about  10°  in  the  boiling  point.  There 
is  also  a  gradual  increase  in  the  specific  gravity. 
Action  of  Amw^onia  and  Amines  on  Chlor acetones. — The  action  of 
orthotoluidine  on  hexachloracetone  yields  orthocresyltrichloracet- 
ainide,  C6H4Me*NH'C2Cl30,  which  crystallizes  in  large  needles 
only  slightly  soluble  in  cold  alcohol.  It  melts  at  66 — 67°,  readily 
remains  in  superfusion,  and  volatilizes  at  215°.  Paratoluidine  yields 
the  corresponding  para-derivative,  which  crystallizes  in  very  short 
rectangular  prisms,  melting  at  79 — 80°,  and  volatilizing  with 
partial  decomposition  at  185°.  It  is  only  slightly  soluble  in  cold 
alcohol. 
With  diethylamine,  hexachloracetone  yields  diethyltrichloracet- 
amide,  which  is  very  soluble  in  alcohol,  and  crystallizes  in  prisms 
which  melt  at  90°  and  volatilize  almost  immediately  with  partial  de- 
composition. With  trimethylamine,  dimethyltrichloracetamide  is 
formed ;  this  is  very  soluble  in  boiling  alcohol,  and  crystallizes  in 
radiating  needles  which  melt  at  104°,  and  sublime  at  195°.  With 
dimethylaniline,  the  reaction  takes  place  only  on  warming,  and  the 
product  is  a  mixture  of  a  violet  coloring  matter,  soluble  in  boiling 
water  but  almost  insoluble  in  ether,  and  very  soluble  in  chloroform, 
with  another  badly  defined  coloring  matter.  Allylamine  yields  allyl- 
trichloracetamide,  soluble  in  alcohol  and  in  chloroform,  and  crystal- 
lizing in  large  tables  which  melt  at  45°  and  volatilize  without  decom- 
position at  190°.  With  hexachloracetone  and  pentachloracetone 
respectively,  ethylenediamine  yields  the  two  derivatives,  CgH^ :  NgHg* 
C2CI3O  and  C2H4 :  KH3-C2HC120.  The  first  is  soluble  in  alcohol,  and 
crystallizes  in  elongated  rhomboidal  plates  which  melt  at  200°  and 
sublime  at  the  same  temperature.  The  second  is  soluble  in  warm 
alcohol,  and  very  soluble  in  eiher.  It  crystallizes  from  alcohol  in 
elongated  parallelograms,  and  from  ether  in  fan-shaped  plates. 
