19481-79-9

Basic information

• Product Name: 2-Iodo-2-methylpropionitrile
• Synonyms: 2-Iodo-2-methylpropionitrile;Propanenitrile, 2-iodo-2-methyl-
• CAS NO: 19481-79-9
• Molecular Formula: C₄H₆IN
• Molecular Weight: 195.00161
• EINECS: -0
• Mol File: 19481-79-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 62°C/15mmHg(lit.)
• Appearance: /
• Density: 1.717 g/cm3(Temp: 19 °C)
• Refractive Index: 1.5130-1.5170
• Storage Temp.: <0°C
• CAS DataBase Reference: 2-Iodo-2-methylpropionitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodo-2-methylpropionitrile(19481-79-9)
• EPA Substance Registry System: 2-Iodo-2-methylpropionitrile(19481-79-9)

Safety Data

• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 19481-79-9(Hazardous Substances Data)

Upstream product

• 7553-56-2 iodine 
• 108-88-3 toluene 
• 1825-33-8 phenylazo-i-butyric acid nitrile 
• 41658-69-9 2-bromo-2-methyl-propionitrile 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 1950-78-3 p-toluenesulfonyl iodide 

Downstream Products

• 10409-07-1 bis(4-methylphenyl)disulfone 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 4124-41-8 p-toluenesulfonylanhydride 
• 98039-88-4 1-cyano-1-methylethyl p-tolyl sulphone 
• 33695-62-4 2-methyl-2-phenylsulfanylpropanenitrile 

Relevant articles and documents

Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur

Dialkyl azo compounds were found to be effective alkyl radical sources for direct alkyl sulfuration with imidazopyridines using elemental sulfur under metal-free conditions. Iodine, an inexpensive and mild reagent, could promote alkyl sulfuration. A variety of quaternary cyanoalkyl radicals were successfully coupled with elemental sulfur. A subsequent C-H sulfuration of imidazopyridines afforded a diverse array of imidazopyridine derivatives bearing cyanoalkylthio groups. The cyano group could be modified and further underwent condensation with 2-aminothiazole to afford an interesting heterocyclic amide. Control experiments showed that iodine could greatly suppress the self-coupling of cyanoalkyl radicals, thus making the sulfuration proceed smoothly.

Iodine atom transfer addition reaction of 1-iodoalkyl phosphonates to alkenes in the presence of α,α′-azoisobutyronitrile (AIBN): Mechanistic aspects

The objectives of this work were to elucidate the mechanistic pathway of the title reaction, which constitutes the first example of a radical iodine atom transfer addition reaction of non-fluorine-containing phosphonates, and to determine whether 2-iodo-2-methylpropionitrile, 8, can serve as a competing iodine donor with the starting diethyl 1-iodoalkyl phosphonates, 1a,b. The title reaction was found to proceed with AIBN as the sole radical initiator, not requiring poisonous tin reagents as co-initiators, and gave diethyl 3-iodoalkylphosphonates 3a-e (the final products of the propagation step, isolated in 59-95% yield), tetramethylsuccinodinitrile, 9, diethyl methylphosphonate, 4 and tetraethyl ethylenebisphosphonate 5 (all termination products, 0-10% yields). The radical character of this reaction was demonstrated using TEMPO as a radical trap. 8 (the intermediate of the initiation step), synthesized independently from AIBN and iodine, caused complete inhibition of the reaction when added to the reaction mixture, indicating that it does not behave as an iodine donor in the transfer stage, but rather as an inhibitor.

Reaction of Arenesulphonyl Halides with Free Radicals. Part 3.

The decomposition of azoisobutyronitrile (AIBN) and t-butyl phenylperacetate in the presence of toluene-p-sulphonyl bromide and iodide were studied; results are explained on the basis of free radical reactions.The relative reactivities of several alkane- and arene-sulphonyl chlorides towards phenyl, benzyl, and trichloromethyl radicals were measured in competition experiments.Results are rationalized on the grounds of a balance between polar effects in the initial and in the transition state.