30306-69-5 Usage
Description
1-IODO-4-NITROBENZENE is an organic compound with the chemical formula C6H4I(NO2). It is a generic chemical reagent known for its versatile applications in various chemical reactions and synthesis processes. It possesses a unique structure with an iodine atom and a nitro group attached to a benzene ring, which contributes to its reactivity and utility in organic chemistry.
Uses
Used in Organic Synthesis:
1-IODO-4-NITROBENZENE is used as a chemical reagent for the stereoselective semihydrogenation of alkynes. This process involves the selective reduction of alkynes to form either cis or trans alkenes, depending on the reaction conditions and the choice of catalyst. The presence of the iodine and nitro groups in 1-IODO-4-NITROBENZENE allows for better control over the stereochemistry of the resulting products.
Used in Pharmaceutical Industry:
1-IODO-4-NITROBENZENE is used as a key intermediate in the formulation of new arylisoquinolones, which are compounds with potential anti-inflammatory activity. These arylisoquinolones can be further modified and optimized to develop novel drugs for the treatment of various inflammatory conditions, such as arthritis, asthma, and other autoimmune diseases.
Preparation
Preparation of 1-iodo-4-nitrobenzene from 4-Nitroaniline.
Principle: Diazonium salts undergo a large number of reactions in which the diazo group is lost as molecular nitrogen and is replaced by variety of other groups (e.g. OH, I, Br, Cl, F, CN, NO2, H, SO2H, Ar) which become attached to the aromatic ring.
Reaction:
Procedure: Take 0.5 g p-nitro aniline, 0.41 ml conc. H2SO4 and 3 ml water in a conical flask. Stir it well and cool to 0-5°C. Add a cold solution of 0.25 g NaNO2 in 0.75 ml distilled water to the above solution. Filter the resultant cold solution, and add the filtrate with stirring to a solution of 1 g KI in 3 ml water taken in a beaker. Filter the product separated out and wash it with water. Dry the product, record the practical yield and re-crystallize it.
Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. The shiny brown crystals of p-iodo nitro benzene separate out. Filter, dry and record the melting point and TLC (using toluene as a solvent).
Synthesis Reference(s)
Journal of the American Chemical Society, 83, p. 1928, 1961 DOI: 10.1021/ja01469a036The Journal of Organic Chemistry, 33, p. 3670, 1968 DOI: 10.1021/jo01273a083
Check Digit Verification of cas no
The CAS Registry Mumber 30306-69-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,0,3,0 and 6 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 30306-69:
(7*3)+(6*0)+(5*3)+(4*0)+(3*6)+(2*6)+(1*9)=75
75 % 10 = 5
So 30306-69-5 is a valid CAS Registry Number.
