4436-27-5

Usage

Purification Methods

Crystallise the iodide from *benzene. [Beilstein 5 III 647, 5 IV 758.]

InChI:InChI=1/C6H2IN3O6/c7-6-4(9(13)14)1-3(8(11)12)2-5(6)10(15)16/h1-2H

Upstream product

• 88-88-0 2,4,6-trinitrochlorobenzene 
• 68630-38-6 pentanitrobenzene 
• 88-89-1 2,4,6-Trinitrophenol 

Downstream Products

• 115164-16-4 1-picryl-pyridinium; iodide 
• 99-35-4 1,3,5-trinitrobenzene 
• 29128-23-2 2,4,6-Trinitro-biphenyl 
• 13141-41-8 2,4,6-trinitrophenyl(phenyl)acetylene 
• 573-83-1 potassium picrate 
• 94988-28-0 picryloacetoacetic ester 
• 3324-58-1 sodium picrate 
• 40864-29-7 picryl thiocyanate 
• 88-89-1 2,4,6-Trinitrophenol 

Relevant academic research and scientific papers

The activation of SNAr reactions by the superstrong electron-withdrawing substituent CF3S(O)=NSO2CF3

The chlorine lability of the 2-nitrochlorobenzene derivative which contains the superstrong electron-withdrawing substituent CF3S(O)=NSO2CF3 in position 4 has been compared with the analogous 4-trifluoromethylsulphonyl derivative and picryl chloride in nucleophilic substitution.During interaction with hard nucleophilic agents, the effect of one superstrong substituent approximately corresponds to the influence of two nitro groups in positions 2 and 4.With soft reagents, picryl chloride is more active than the compound containing the CF3S(O)=NSO2CF3 group, polarizable only with difficulty.

Reactions of 1-X-2,4,6-Trinitrobenzenes and 1-X-2,4-Dinitrobenzenes with Hydroxide Ions. Comparison of the Relative Rates of Nucleophilic Attack at Substituted and Unsubstituted Ring-Positions

Kinetic and equilibrium measurements are reported for the reactions with hydroxide ions of 1-X-2,4,6-trinitrobenzenes (X = H, F, Cl, Br, I) in water and of 1-X-2,4-dinitrobenzenes in dimethyl sulphoxide-water (80:20, v/v).Attack at unsubstituted ring-positions results in the formation of ?-adducts while attack at halogen-substituted positions leads to 2,4,6-trinitro- or 2,4-dinitro-phenolate ions by nucleophilic substitution; the rate constants for these processes are compared.The results provide evidence for two types of steric effects: (i) increasing the size of the halogen atom results in disruption of the planarity of the nitro-groups, giving a general decrease in reactivity at both unsubstituted and halogen-substituted positions; (ii) unfavourable steric and electrostatic repulsion between entering and leaving groups slows the attack of hydroxide at carbon atoms carrying Cl, Br, or I.In water there is evidence for ionization of added hydroxy groups (3)> and for nucleophilic displacement of nitrite by hydroxide within the 3-hydroxy adducts (2) and (3).Contrary to a recent report the reaction of hydroxide ions with nitro compounds to form hydroxy adducts is found to occur without the observation of spectrophotometrically detectable intermediates.

Decomposition of Hexachloroacetone in Dimethyl Sulphoxide Solution: a Source of Trichloromethanide Anions

Hexachloroacetone (HCA) decomposes in dimethyl sulphoxide solution at room temperature.In the presence of an excess of 1,3,5-trinitrobenzene (TNB) the progress of the reaction can be monitored by the appearence of the visible absorption characteristic of the formation of the trichloromethyl Meisenheimer adduct of TNB in nearly quantitative yield (2 mol of adduct per mol of HCA).The reaction is slower than the decomposition of trichloroacetic acid under the same conditions, the difference being attributable to a large negative entropy of activation.The reaction rate is markedly increased by the addition of water and slightly depressed by addition of acid.The kinetics are consistent with a rate-limiting breakdown of the gem-diol hydrate of HCA into trichloroacetic acid and trichloromethanide anions, followed by the more rapid decomposition of trichloroacetic acid.

Nitrocarbons. 4. Reaction of Polynitrobenzenes with Hydrogen Halides. Formation of Polynitrohalobenzenes

Hexanitrobenzene and pentanitrobenzene in benzene solution react with hydrogen halides (HCl, HBr, HI, but not HF) at 25 deg C to produce high yields of pentanitrohalobenzenes and 2,3,4,6-tetranitrohalobenzenes, respectively.Pentanitrofluorobenzene also reacts readily with HCl to yield 3-chloro-2,4,5,6-tetranitrofluorobenzene, but the other pentanitrohalobenzenes are much less reactive. 1,2,3,5- and 1,2,4,5-tetranitrobenzenes react rapidly with concentrated hydrochloric or hydrobromic acids at reflux to form picryl halides and 1-halo-2,4,5-trinitrobenzenes, respectively; pentanitrotoluene reacts very slowly under these conditions to form 3-halo-2,4,5,6-tetranitrotoluenes in lower yields.The scope and limitations of this regioselective reaction are defined, and comparison is made to related reactions.A mechanism is presented and discussed.