56905-18-1

Basic information

• Product Name: methyl 2-iodopropanoate
• Synonyms: Methyl 2-iodopropanoate
• CAS NO: 56905-18-1
• Molecular Formula: C₄H₇IO₂
• Molecular Weight: 214.0016
• Mol File: 56905-18-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 171.6°C at 760 mmHg
• Flash Point: 57.6°C
• Density: 1.825g/cm³
• Vapor Pressure: 1.38mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: methyl 2-iodopropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-iodopropanoate(56905-18-1)
• EPA Substance Registry System: methyl 2-iodopropanoate(56905-18-1)

Safety Data

• Hazardous Substances Data: 56905-18-1(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 292638-85-8 acrylic acid methyl ester 
• 5445-17-0 Methyl 2-bromopropionate 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 67-56-1 methanol 
• 598-80-1 2-iodopropionic acid 
• 186581-53-3 diazomethane 
• 18791-45-2 (R)-2-iodo-propionic acid 

Downstream Products

• 2605-68-7 methyl 2-(triphenylphosphoranylidene)propionate 
• 83037-73-4 6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone 
• 52888-49-0 methyl N-(2,6-dimethylphenyl)alaninate 
• 56904-90-6 (1-methoxy-1-oxopropan-2-yl)triphenylphosphonium iodide 

Relevant articles and documents

Photoiodocarboxylation of Activated C=C Double Bonds with CO2 and Lithium Iodide

The photolysis at 254 nm of lithium iodide and olefins 1 carrying an electron-withdrawing Z-substituent in CO2-saturated (1 bar) anhydrous acetonitrile at room temperature produces the atom efficient and transition metal-free photoiodocarboxylation of the C=C double bond. The reaction proceeds well for terminal olefins 1 to form the new C-I and C-C σ-bonds at the α and β-positions of the Z-substituent, respectively, and is strongly inhibited by polar protic solvents or additives. The experimental results suggest that the reaction channels through the radical anion [CO2?-] in acetonitrile, yet involves different intermediates in aqueous medium. The stabilizing ion-quadrupole and electron donor-acceptor interactions of CO2 with the iodide anion play a crucial role in the reaction course as they allow CO2 to penetrate the solvation shell of the anion in acetonitrile, but not in water. The reaction paths and the reactive intermediates involved under different conditions are discussed.

Erratum: A multicomponent Ni-, Zr-, and cu-catalyzed strategy for enantioselective synthesis of alkenyl-substituted quaternary carbons, (Angewandte Chemie - International Edition (2014) 53 (1910-1914) DOI: 10.1002/anie.201309456)

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α-Iodination of Some Aliphatic Acids. Substituent Effect and Optimum Conditions

The chlorosulfonic acid promoted α-iodination of some aliphatic acids in 1,2-dichloroethane has been studied.In contrast to the bromination, the effect of substituents on the rate shows not only a polar effect but also a steric effect in view of Taft's equation: , where ρ? = -1.20 and δ = 1.55 at 80 deg C.The transition state is discussed, which involves the electrophilic addition of I2 to a ketene intermediate.Aliphatic acids with less steric hindrance at the α-position, except acetic acid, are α-iodinated in good yields (ca. 80-100percent).The optimumconditions for α-iodination of long-chain aliphatic acids with caprylic acid as a model substrate are described.