558-17-8

Usage

Uses

Used in Chemical Synthesis:
2-IODO-2-METHYLPROPANE is used as a chemical reagent for organic synthesis, particularly in the production of various organic compounds and materials. Its reactivity allows it to participate in a wide range of chemical reactions, such as substitution, elimination, and rearrangement reactions, making it a valuable tool in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
2-IODO-2-METHYLPROPANE serves as a pharmaceutical intermediate, playing a crucial role in the development and production of various drugs. Its ability to form stable intermediates and participate in key reactions makes it an essential component in the synthesis of pharmaceutical compounds, contributing to the advancement of new medications and therapies.
Additionally, 2-IODO-2-METHYLPROPANE can be used in other industries, such as the agrochemical and polymer industries, where its reactivity and stability are harnessed for the production of various products and materials.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 609, 1995 DOI: 10.1016/0040-4039(94)02315-3

Purification Methods

Vacuum distillation has been used to obtain a distillate which remained colourless for several weeks at -5o. More extensive treatment has been used by Boggs, Thompson and Crain [J Phys Chem 61 625 1957] who washed with aqueous NaHSO3 solution to remove free iodine, dried this for 1hour over Na2SO3 at 0o, and purified it by four or five successive partial freezings of the liquid to obtain colourless material and was stored at -78o with Ag wool. [Beilstein 1 IV 300.]

Upstream product

• 513-38-2 Isobutyl iodide 
• 115-11-7 isobutene 
• 1605-73-8 t-Butyl radical 
• 507-19-7 t-butyl bromide 
• 65538-01-4 Phenylperfluoroisopropyl sulfide 
• 594-19-4 tert.-butyl lithium 
• 75-65-0 tert-butyl alcohol 
• 594-70-7 2-Methyl-2-nitropropane 
• 10034-85-2 hydrogen iodide 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 69745-48-8 1-tert-butyl-cyclopentanol 
• 110-06-5 di-tert-butyl disulfide 
• 40207-97-4 n-C₄H₉BI₂ 
• 27545-47-7 4-CH₃C₆H₄BI₂ 

Downstream Products

• 31084-58-9 N-tert-Butyl-3-methoxyaniline 
• 16881-32-6 tert-butyl N-(benzyloxycarbonyl)glycinate 
• 28009-80-5 1,3-acetonedicarboxylic acid di(tert-butyl) ester 
• 16881-34-8 N-benzyloxycarbonyl-L-phenylalanine t-butyl ester 
• 13221-94-8 3-(tert-butyl)pentane-2,4-dione 
• 4210-60-0 t-butylmalonodinitrile 
• 118220-92-1 3-(Hydroxy-phenyl-methyl)-hexan-2-one 
• 118220-82-9 erythro-3-(α-Hydroxybenzyl)-5,5-dimethyl-2-hexanone 
• 118220-82-9 threo-3-(α-Hydroxybenzyl)-5,5-dimethyl-2-hexanone 
• 74676-20-3 erythro-3-(α-Hydroxybenzyl)-2-hexanone 
• 74676-20-3 threo-3-(α-Hydroxybenzyl)-2-hexanone 
• 131457-29-9 p-methoxybenzene-azo-α,α-dimethylethane 
• 937-33-7 N-tert-butylaniline 
• 3282-56-2 4-tert-butylnitrobenzene 

Relevant academic research and scientific papers

EINE EINFACHE METHODE ZUR DARSTELLUNG TERTIAERER IODIDE

Hindered alkyl iodides may be prepared conveniently by treatment of the corresponding alcohols with magnesium iodide in n-pentane.

Photoinduced Palladium-Catalyzed Dicarbofunctionalization of Terminal Alkynes

Herein, a conceptually distinct approach was developed that allowed for the dicarbofunctionalization of alkynes at room temperature using simple, bench-stable alkyl iodides and a second molecule of alkyne as coupling partner. Specifically, the photochemical activation of palladium complexes enabled this strategic dicarbofunctionalization via addition of alkyl radicals from secondary and tertiary alkyl iodides and formation of an intermediate palladium vinyl complex that could undergo subsequent Sonogashira reaction with a second alkyne molecule. This alkylation–alkynylation sequence allowed the one-step synthesis of 1,3-enynes including heteroarenes and biologically active compounds with high efficiency without exogenous photosensitizers or oxidants and now opens up pathways towards cascade reactions via photochemical palladium catalysis.

Visible-light-mediated multicomponent reaction for secondary amine synthesis

The widespread presence of secondary amines in agrochemicals, pharmaceuticals, natural products, and small-molecule biological probes has inspired efforts to streamline the synthesis of molecules with this functional group. Herein, we report an operationally simple, mild protocol for the synthesis of secondary amines by three-component alkylation reactions of imines (generated in situ by condensation of benzaldehydes and anilines) with unactivated alkyl iodides catalyzed by inexpensive and readily available Mn2(CO)10. This protocol, which is compatible with a wide array of sensitive functional groups and does not require a large excess of the alkylating reagent, is a versatile, flexible tool for the synthesis of secondary amines.

Visible-Light-Mediated C-I Difluoroallylation with an α-Aminoalkyl Radical as a Mediator

Herein, we report a protocol for direct visible-light-mediated C-I difluoroallylation reactions of α-trifluoromethyl arylalkenes with alkyl iodides at room temperature with an α-aminoalkyl radical as a mediator. The protocol permits efficient functionalization of various α-trifluoromethyl arylalkenes with cyclic and acyclic primary, secondary, and tertiary alkyl iodides and is scalable to the gram level. This mild protocol uses an inexpensive mediator and is suitable for late-stage functionalization of complex natural products and drugs.

A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity

α-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms have been proposed.

A mild and highly chemoselective iodination of alcohol using polymer supported DMAP

The synthesis of organic compounds using polymer supported catalysts and reagents, where the required product is always in solution, has been of great interest in recent years, both in industries and academia especially in pharmaceutical research. Here, a simple and efficient method for conversion of alcohols into their iodides in high yield using polymer supported 4-(Dimethylamino)pyridine (DMAP) is described. Polymer supported DMAP is used in catalytic amount and is recovered and reused several times. Additionally, this method is highly chemoselective. [Figure not available: see fulltext.]

An efficient and selective method for the iodination and bromination of alcohols under mild conditions

A straightforward and effective procedure for the conversion of a variety of alcohols into the corresponding alkyl iodides and bromides is described using KX/P2O5 (X = I, Br). The reactions were easily carried out in acetonitrile under mild conditions. Using this method, the selective conversion of benzylic alcohols in the presence of aliphatic alcohols was achieved.

Iodine-hexamethyldisilane (HMDS)-mediated anomerization of peracetylated 1,2-trans-linked alkyl and aryl glycosides

Treatment of peracetylated alkyl and aryl 1,2-trans-glycosides with iodine in the presence of HMDS has been found to result in the anomerization leading to the formation of the respective 1,2-cis-glycosides. In the case of alkyl glycosides with aglycons of short alkyl chain length complete anomerization to the α-glycosides was observed while with those of longer chain length the process was found to be incomplete. The observations have been interpreted mechanistically.

Iodination of alcohols over Keggin-type heteropoly compounds: A simple, selective and expedient method for the synthesis of alkyl iodides

Different catalysts derived from Keggin-type heteropoly compounds were prepared and their catalytic activities have been compared in the iodination of benzyl alcohol with KI under mild reaction conditions. A high catalytic activity was found over tungstophosphoric acid supported on silica and titania. The effect of catalyst loading, iodine source and the nature of substituents on the aromatic ring of benzyl alcohol were investigated. Finally, several competitive reactions were studied between structurally diverse alcohols. This protocol provides a mild and expedient way for the conversion of various alcohols to their corresponding alkyl iodides with high selectivity.

Silicaphosphine (Silphos): A filterable reagent for the conversion of alcohols and thiols to alkyl bromides and iodides

Silicaphosphine (Silphos), [P(Cl)3-n(SiO2) n], as a new heterogeneous reagent is introduced. This reagent converts alcohols and thiols to their corresponding bromides and iodides in the presence of X2 (X=Br, I) in refluxing CH3CN in high to quantitative yields. Use of Silphos provides a highly practical method for the easy separation of the Silphos oxide byproduct by a simple filtration.