( 279 ) 



3-aminophenol (m.p. 165°) and substitution of the NHj-group in this 

 substance by OH. 



The monoethylether of 5-nitroresoi'cinol (m.p. 80*^) was prepared 

 (quite analogous to the methylether) from 5-nitro-3-aminophenetol; 

 the 3-Cl (Br) 5-nitrophenoi was obtained by substituting the NH, -group 

 in the 5-nitro-3-aminoanisol by CI (Br) according to Sandmeyer and 

 then heating the 3-Cl (Br)-5-nitroanisol so obtained m.p. (101° ^) and 

 88^); with HCl as directed. We tiien obtain, in addition to CHjCl, 

 the desired product 3-Ci (Br) 5-nitrophenol (m.p. 147° and 145°). 



The 3-5-substituted phenols so obtained readily assimilate three 

 atoms of bromine on treatment with bromine water and three nitro- 

 groups are introduced on nitration with H NO, (Sp. gr. 1.52) and 

 Hj SO4. These last compounds, which all contain four NO^-groups 

 resemble picric acid, tetra- and pentanitrophenol. From a mixture of 

 nitric and sulphuric acids they crystallise as colourless crystals which 

 are turned yellow by a small quantity of water; the compounds 

 have a bitter taste, an acid reaction and communicate a strong yellow 

 colour to organic tissues (the skin), others strongly attach the skin and 

 all are possessed of explosive properties owing to the presence of 

 four NOj-groups ^). 



on OH OH OH 



/\ /\ /\ /\ 



^"OjX /CH3 NOaX /OH NOaX /OCHjCOCsHs) No\ /Cl(Br) 

 \/ \/ \^ 80° \/ 145° 



I' I' y 1 



OH OH OH OH 



NOü/XnOs N0s/\n02 NOs/^XnOs NOj/XnOj 



U75°J 1 152° 1 I 1150 I - ■ I 147° I 



XO-A /CH3 NOjV /OH NO^X /OCHsfOCjHs) NOjV/ClCBr) 



NO, NO2 NO, ^^^° NO;,'^'" 



withlH^O withlHsO withlNHj withlNHaCgHs 



OH OH OH OH 



NO3/XNO2 NOa/X^^O, NOjy^X^Os NOs/X^O, 



H0\ /CH3 H0\ /OH NHoX /NHj CbHjHNV /NHCsHs 



NO» NO2 NOo NOo 



In this scheme are given only the melting points of the as yet 

 unknown compounds. 



Tetranitro-m. cresol yields on boiling with water trinitroorcinol ; 



1) 91° according to de Kock Rec. 20, 113. 



-) A comparative research as to these properties in the different compounds 

 has not vet been instituted. 



