91358-53-1

Basic information

• Product Name: Benzenepropanoic acid, a-iodo-, methyl ester
• CAS NO: 91358-53-1
• Molecular Formula: C10H11IO2
• Molecular Weight: 290.101
• Mol File: 91358-53-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenepropanoic acid, a-iodo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, a-iodo-, methyl ester(91358-53-1)
• EPA Substance Registry System: Benzenepropanoic acid, a-iodo-, methyl ester(91358-53-1)

Safety Data

• Hazardous Substances Data: 91358-53-1(Hazardous Substances Data)

Upstream product

• 369-57-3 benzenediazonium tetrafluoroborate 
• 292638-85-8 acrylic acid methyl ester 
• 70288-60-7 methyl 2-bromo-3-phenylpropionate 
• 62-53-3 aniline 
• 67-56-1 methanol 
• 104-55-2 3-phenyl-propenal 
• 49769-78-0 2-benzyl-malonic acid dimethyl ester 
• 124604-05-3 C₁₂H₁₃IO₄ 
• 1649946-33-7 C₁₁H₁₁IO₄ 
• 100-39-0 benzyl bromide 
• 54561-75-0 2-benzyl-3-methoxy-3-oxopropanoic acid 

Downstream Products

• 103-25-3 3-phenylpropanoic acid methyl ester 
• 621-82-9 Cinnamic acid 
• 68521-58-4 1-thiocyanato-1-methoxycarbonyl-2-phenylethane 

Relevant articles and documents

The synthesis of α-azidoesters and geminal triazides

Three simple methods for the synthesis of geminal triazides are described: Starting from 1) 3-oxocarboxylic acids, 2) iodomethyl ketones, or 3) terminal olefins, a range of triazidomethyl ketones can be constructed under mild oxidative reaction conditions by the use of IBX-SO3K, a sulfonylated derivative of 2-iodoxybenzoic acid (IBX), and NaN3 as an azide source. This is the first report of representatives of this novel class of triazide compounds: Despite their high nitrogen content, the geminal triazides are easy to handle, even when preparative-scale syntheses are performed. (Caution: These procedures still require protective measures!) The triazides are now broadly available for further studies regarding their properties and reactivity. Furthermore, we show how the method can be used to provide α-azidoesters, which are potential building blocks for amino acids. Either/or: Geminal triazides are rapidly constructed with broad scope by the use of oxocarboxylic acids, iodomethyl ketones, or terminal olefins as starting substrates in oxidative azidations with a mild derivative of 2-iodoxybenzoic acid and sodium azide. Along with this little-studied class of organic azides, α-azidoesters were also synthesized.

A substrate-driven approach to determine reactivities of α,β-unsaturated carboxylic esters towards asymmetric bioreduction

The degree of C=C bond activation in the asymmetric bioreduction of α,β-unsaturated carboxylic esters by ene-reductases was studied, and general recommendations to render these "borderline-substrates" more reactive towards enzymatic reduction are proposed. The concept of "supported substrate activation" was developed. In general, an additional α-halogenated substituent proved to be beneficial for enzymatic activity, whereas β-alkyl or β-aryl substituents were detrimental for the reactivity of nonhalogenated substrates, and α-cyano groups showed little effect. The alcohol moiety of the ester functionality was found to have a strong influence on the reaction rate. Overall, activities were determined by both steric and electronic effects. Biotransformation: The asymmetric bioreduction of α,β-unsaturated carboxylic esters by ene-reductases could be tuned by varying the degree of C=C bond activation (see scheme). An additional α-halogenated substituent proved to be beneficial for enzymatic activity, whereas β-alkyl or β-aryl substituents were detrimental for the reactivity of nonhalogenated substrates. Copyright

IODOARYLATION OF UNSATURATED COMPOUNDS

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