1809-05-8

Basic information

• Product Name: 3-IODOPENTANE
• Synonyms: 3-IODOPENTANE;1-Ethylpropyl iodide
• CAS NO: 1809-05-8
• Molecular Formula: C₅H₁₁I
• Molecular Weight: 198.05
• EINECS: 217-313-5
• Mol File: 1809-05-8.mol

Chemical Properties

• Melting Point: -85.6°C (estimate)
• Boiling Point: 154.22°C (estimate)
• Flash Point: 44.6 °C
• Appearance: /
• Density: 1.5047
• Vapor Pressure: 5.82mmHg at 25°C
• Refractive Index: 1.4952
• CAS DataBase Reference: 3-IODOPENTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-IODOPENTANE(1809-05-8)
• EPA Substance Registry System: 3-IODOPENTANE(1809-05-8)

Safety Data

• Hazardous Substances Data: 1809-05-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Iodopentane is used as a synthetic intermediate for the production of various organic compounds. Its alkyl iodide functional group allows it to participate in a range of chemical reactions, making it a valuable reagent in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Research:
In the field of chemical research, 3-Iodopentane is employed as a model compound to study the properties and reactivity of halogenated hydrocarbons. It is particularly useful for investigating the effects of iodine substitution on the chemical behavior of alkanes, as well as for understanding the mechanisms of reactions involving alkyl iodides.
Used in Material Science:
3-Iodopentane is utilized as a precursor in the development of new materials, such as polymers and advanced composites. Its unique chemical structure and reactivity contribute to the creation of novel materials with improved properties, such as enhanced thermal stability, mechanical strength, or electrical conductivity.
Used in Analytical Chemistry:
3-Iodopentane serves as a reference compound in analytical chemistry, particularly in techniques like gas chromatography and mass spectrometry. Its distinct chemical properties and predictable behavior under various conditions make it an ideal standard for calibrating instruments and validating analytical methods.
Used in Pharmaceutical Industry:
3-Iodopentane is used as a building block in the synthesis of certain pharmaceutical compounds, including drugs for the treatment of various diseases. Its presence in the molecular structure of these compounds can influence their pharmacological properties, such as solubility, bioavailability, or interaction with biological targets.
Used in Agrochemical Industry:
In the agrochemical industry, 3-Iodopentane is employed as a starting material for the synthesis of pesticides and other crop protection agents. Its chemical versatility enables the development of new active ingredients with improved efficacy, selectivity, and environmental compatibility.
Used in Industrial Processes:
3-Iodopentane is utilized in various industrial processes, such as the production of specialty chemicals, intermediates, and additives. Its unique properties and reactivity make it a key component in the manufacturing of a wide range of products, from plastics and coatings to lubricants and adhesives.

InChI:InChI=1/C5H11I/c1-3-5(6)4-2/h5H,3-4H2,1-2H3

Upstream product

• 26184-62-3 (S)-2-pentanol 
• 584-02-1 2-pentanol 
• 1191-96-4 ethylcyclopropane 
• 1809-15-0 bis(1-ethylpropyl)phosphonate 
• 10034-85-2 hydrogen iodide 
• 6032-29-7 (+/-)-2-pentanol 
• 7553-56-2 iodine 
• 38011-62-0 3-pentyl diphenyl phosphinite 
• 74-88-4 methyl iodide 
• 109-66-0 pentane 

Downstream Products

• 88-09-5 2-Ethylbutanoic acid 
• 646-04-8 (E)-pent-2-ene 
• 1809-10-5 3-bromopentane 
• 109-66-0 pentane 
• 18093-68-0 4--buttersaeure 
• 3042-56-6 3-(1-naphthyl)pentane 
• 19398-77-7 3,4-diethylhexane 
• 63929-87-3 1-(1-Ethyl-propoxy)-3-nitro-benzene 
• 75072-46-7 3,5-diethylheptan-4-one 
• 584-02-1 2-pentanol 
• 75-07-0 acetaldehyde 
• 123-38-6 propionaldehyde 
• 96-22-0 pentan-3-one 
• 640767-47-1 2-(1-ethyl-propoxy)-phenylamine 

Relevant articles and documents

NaIO4-KI-NaN3 as a new reagent system for C-H functionalization in hydrocarbons

The NaIO4-KI-NaN3 combination has been found to be an efficient, reliable, and inexpensive reagent system for mono- and 1,2-difunctionalization of hydrocarbons via C-H bond activation to afford vicinal azido- and acetoxy iodinations of cyclic hydrocarbons.

Nickel-catalyzed Negishi cross-couplings of secondary nucleophiles with secondary propargylic electrophiles at room temperature

(Chemical Equation Presented) Mild thing: The first nickel-based catalysts for cross-couplings of secondary organometallic nucleophiles with secondary alkyl electrophiles have been developed. Thus, Negishi reactions proceed under mild conditions (at room temperature with no basic activators) in the presence of NiCl2·glyme and a tridentate ligand (see scheme).

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.

Direct bromination and iodination of non-activated alkanes by hypohalite reagents

The direct functionalisation of alkanes through bromination and iodination has been successfully achieved. The combination of stoichiometric mixtures of elemental halogen and sodium alkoxides leads to the formation of alkyl hypobromites and hypoiodites as reagents. The halogenation occurs without external photostimulation under thermal reaction conditions. Georg Thieme Verlag Stuttgart.

New iodination reactions of saturated hydrocarbons

Unactivated C-H bonds react with iodine when exposed to trimethylsilyl azide in the presence of a hypervalent iodine reagent or, alternatively, to aqueous H2O2, acetic anhydride, and sodium azide (see scheme). (Chemical Equation Presented).

Direct Iodination of Alkanes

(Matrix presented) A cheap and efficient iodination of hydrocarbons can be achieved by generating tert-butyl hypoiodite from iodine and sodium tert-butoxide. The alkane is reactant and solvent, and this metal-free process provides a clean solution for their direct iodination.

Cross-Couplings of Unactivated Secondary Alkyl Halides: Room-Temperature Nickel-Catalyzed Negishi Reactions of Alkyl Bromides and Iodides

The development of a nickel- or palladium-catalyzed method for cross-coupling unactivated secondary alkyl halides has been a long-standing challenge in synthetic chemistry. This communication describes a simple catalyst system-Ni(cod)2/s-Bu-Pybox-that achieves room-temperature Negishi reactions of an array of functionalized primary and secondary alkyl bromides and iodides. Copyright

First examples of superelectrophile initiated iodination of alkanes and cycloalkanes

Direct iodination of alkanes and cycloalkanes in the presence of superelectrophiles has been accomplished for the first time. The reactions of saturated hydrocarbons with I2 in the presence of CCl4·2AlI3 at -20°C afforded monoiodides in good yields and selectivities.

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.