513-48-4

Usage

Uses

Used in Organic Synthesis:
2-Iodobutane is used as a reagent in organic synthesis for the production of various chemicals. Its ability to act as an electrophile in reactions makes it a versatile compound for creating a wide range of organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Iodobutane is used as a pharmaceutical intermediate. It plays a crucial role in the synthesis of various drugs, contributing to the development of new medications and therapies.
As a Solvent:
2-Iodobutane is also utilized as a solvent in the chemical industry. Its properties make it suitable for dissolving a variety of substances, facilitating various chemical reactions and processes.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Halogenated aliphatic compounds, such as 2-Iodobutane, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Purification Methods

Purify the iodide by shaking with conc H2SO4, then washing it with water, aqueous Na2SO3 and again with water. Dry (MgSO4) and distil. Alternatively, pass it through a column of activated alumina before distillation, or treat with bromine, followed by extraction of the free halogen with aqueous Na2S2O3, thoroughly washing with water, drying and distilling. It is stored over silver powder and distilled before use. [Beilstein 1 IV 272.]

InChI:InChI=1/C4H9I/c1-3-4(2)5/h4H,3H2,1-2H3/t4-/m0/s1

Upstream product

• 106-98-9 1-butylene 
• 78-92-2 iso-butanol 
• 2314-97-8 iodotrifluoromethane 
• 590-18-1 (Z)-2-Butene 
• 693-02-7 hex-1-yne 
• 106-97-8 n-butane 
• 1708-29-8 2,5-dihydrofuran 
• 10034-85-2 hydrogen iodide 
• 92097-00-2 i-butyl-s-butylether 
• 22238-17-1 tri-sec-butylborate 
• 1730-97-8 (S)-2-methylbutyraldehyde 
• 7553-56-2 iodine 
• 107-01-7 butene-2 
• 513-48-4 2-butyl iodide 

Downstream Products

• 25991-45-1 1-(1-methylpropyl)piperidine 
• 83-27-2 sec-butyl-malonic acid diethyl ester 
• 22921-59-1 2-(1-methylpropyloxy)benzaldehyde 
• 105254-41-9 N-ethyl-N-sec-butyl-aniline 
• 105-43-1 3-methylvaleric acid 
• 4372-15-0 sec-butyl-malonic acid 
• 1540-31-4 ethyl 2-acetyl-3-methylpentanoate 
• 139377-71-2 (E)-(4-methylhex-1-en-1-yl)benzene 
• 124292-34-8 4-methyl-3-phenylhex-1-ene 
• 66292-26-0 4-methyl-1,1-diphenylhex-1-ene 
• 124292-35-9 4-methyl-3,3-diphenylhex-1-ene 
• 135-98-8 sec-Butylbenzene 
• 117068-03-8 2-Methyl-1-(1H-pyrrol-2-yl)-butan-1-one 
• 117068-04-9 3-sec-Butyl-1H-pyrrole-2-carbaldehyde 

Relevant academic research and scientific papers

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.

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.]

A transition-metal-free Heck-type reaction between alkenes and alkyl iodides enabled by light in water

A transition-metal-free coupling protocol between various alkenes and non-activated alkyl iodides has been developed by using photoenergy in water for the first time. Under UV irradiation and basic aqueous conditions, various alkenes efficiently couple with a wide range of non-activated alkyl iodides. A tentative mechanism, which involves an atom transfer radical addition process, for the coupling is proposed.

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.

Salts of Mosher's thioacid: agents for determining the enantiomer excess of SN2 substrates

The racemic and the (S)-enantiomer of Mosher's thioacid, 2-methoxy-2-trifluoromethylphenylacetic thioacid, form air-stable salts with Proton Sponge [1,8-bis(dimethylamino)naphthalene]. These salts are powerful nucleophiles that react cleanly (SN2 inversion) in CDCl3 with optically active alkyl halides ranging in reactivities from unactivated alkyl bromides and iodides to benzylic bromides. The diastereomeric excess (de) of the thioester products indicates the enantiomeric excess (ee) of the starting alkyl halides.

Mechanism of decomposition of quasiphosphonium intermediates: Borderline SN1 character of alkyl-oxygen fission in sec-alkyloxyphosphonium salts

Short-lived alkoxyphosphonium intermediates have been detected in the interactions of alkyl diphenylphosphinites ROPPh2 (R = Et, Pr i, Bu8, and 3-pentyl) with iodomethane at room temperature. Phosphorus chemical shifts for the sec-alkoxy(methyl) diphenylphosphonium iodides (δp 68.6-68.7 ppm) are at slightly higher field than for ethoxy(methyl)diphenylphosphonium iodide (δp 72.4 ppm), in accord with higher electron density at phosphorus in the secondary alkyl sytems. Relative rates of decomposition in CDCl3 (Me > Et > Pri ? neopentyl) are in accord with SN2-type cleavage of the R-O bond but within the secondary alkyl series the relative rates (Pri 8 N1 mechanism is proposed.

Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective and neutral system for the facile conversion of alcohols, thiols and selenols to alkyl halides in the presence of halide ions

A mixture of triphenylphosphine (Ph3P) and 2,3-dichloro-5,6-dicyanobenzoquinone in CH2Cl2 affords a complex which in the presence of R4NX (X=Cl, Br, I) converts alcohols, thiols and selenols into their corresponding alkyl halides in high yields at room temperature. The method is highly selective for the conversion of 1° alcohols in the presence of 2° ones and also 1° and 2° alcohols in the presence of 3° alcohols, thiols, epoxides, trimethylsilyl- and tetrahydropyranyl ethers, 1,3 dithianes, disulfides, and amides.

Mild conversion of alcohols to alkyl halides using halide-based ionic liquids at room temperature

Formula presented Alcohols were efficiently converted to alkyl halides using 1-n-butyl-3-methylylimidazolium halides (ionic liquids) in the presence of Bronsted acids at room temperature. The alkyl halide products were easily isolated from the reaction mixture via simple decantation or extraction, and the 1-n-butyl-3-methylimidazolium cation could be recycled for further uses.

The first efficient iodination of unactivated aliphatic hydrocarbons

No heavy metals, no enzymes, and a simple protocol: the direct iodination of aliphatic hydrocarbons, which has not been possible to date, can now be carried out in multiphase systems [see for example Eq. (l)]. In situ generated tetraiodomethane serves as a key intermediate in this selective radical chain reaction initiated by a single electron transfer. This room-temperature, efficient transformation is highly regioselective, easy to work-up, and hence widely applicable.