2-Iodopropane
[CAS# 75-30-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Alkane
• Name: 2-Iodopropane
• Synonyms: Isopropyl iodide
• Molecular Formula: C₃H₇I
• Molecular Weight: 169.99
• CAS Registry Number: 75-30-9
• EC Number: 200-859-3
• SMILES: CC(C)I

Properties

• Density: 1.703
• Melting point: -90 °C
• Boiling point: 90 °C
• Refractive index: 1.4982
• Flash point: 42 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-H302-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 2392

Discovery and Applications

2-Iodopropane, with the chemical formula C₃H₇I, is an alkyl halide consisting of a propane molecule substituted with an iodine atom at the 2-position. This compound is well known for its reactivity and various industrial applications, particularly in organic synthesis and as a starting material for pharmaceuticals and agrochemicals.

The discovery of 2-iodopropane was part of a broader study of halogenated hydrocarbons in the early 20th century. Scientists explored ways to introduce halogen atoms into organic molecules to modify their properties and enhance their utility in chemical reactions. The development of synthetic routes for 2-iodopropane involved the halogenation of propane derivatives under controlled conditions to achieve selective iodination.

The synthesis of 2-iodopropane typically involves the reaction of propane or propylene with iodine and a suitable catalyst. Propylene can also react directly with iodine in the presence of a catalyst to form 2-iodopropane. These reactions produce 2-iodopropane, which can be purified and isolated for use in a variety of applications.

2-Iodopropane is a versatile building block in organic synthesis. The electron-withdrawing nature of the iodine atom makes it useful in reactions involving nucleophilic substitution and metal-catalyzed coupling reactions for the synthesis of complex organic molecules, including pharmaceutical intermediates, agrochemicals, and specialty chemicals.

In medicinal chemistry, 2-iodopropane is used as a precursor for the synthesis of drugs and bioactive compounds. It participates in reactions to alter the molecular structure and enhance drug potency, selectivity, and pharmacokinetic properties. The compound is valuable for medicinal chemistry research due to its ability to undergo a wide range of transformations.

Similar to pharmaceuticals, 2-iodopropane is used in agrochemicals to synthesize herbicides, fungicides, and insecticides. Its reactivity allows for the introduction of specific functional groups, which improves the efficacy and selectivity of agrochemicals, aiding in crop protection and pest management.

2-iodopropane is useful as a specialty solvent in various industrial processes and chemical laboratories. The solvent properties of 2-iodopropane and its relatively low toxicity compared to other halogenated solvents make it suitable for specific applications where solubility and chemical compatibility are critical.

Due to its halogenated nature, 2-iodopropane should be handled with care in a controlled environment. Safety procedures should be followed to minimize exposure and potential hazards when using 2-iodopropane in industrial and laboratory settings. Regulatory guidelines govern its production, handling, and disposal to ensure safety and environmental protection.

References

2019. Synthesis and Structure of 4-Het(aryl)-3,5,5-trimethoxycarbonyl-2-pyrrolidones. Russian Journal of General Chemistry, 89(7).
DOI: 10.1134/s1070363219070260

2020. Production of Adipic Acid Derivatives from d-Glucaric Acid by Hydrodeoxygenation Mediated with Hydroiodic Acid. Catalysis Letters, 150(7).
DOI: 10.1007/s10562-020-03312-x