5345-61-9

Basic information

• Product Name: butyl iodoacetate
• Synonyms: acetic acid, 2-iodo-, butyl ester; Butyl iodoacetate
• CAS NO: 5345-61-9
• Molecular Formula: C₆H₁₁IO₂
• Molecular Weight: 242.0548
• Mol File: 5345-61-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 220.1°C at 760 mmHg
• Flash Point: 86.9°C
• Density: 1.614g/cm³
• Vapor Pressure: 0.115mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: butyl iodoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: butyl iodoacetate(5345-61-9)
• EPA Substance Registry System: butyl iodoacetate(5345-61-9)

Safety Data

• Hazardous Substances Data: 5345-61-9(Hazardous Substances Data)

Upstream product

• 18991-98-5 n-butyl bromoacetate 

Downstream Products

• 29513-56-2 n-butyl 4-oxo-4-phenylbutanoate 

Relevant articles and documents

Use of enantio-, chemo- and regioselectivity of acylase I. Resolution of polycarboxylic acid esters

Acylase I was used to catalyze the enantioselective butanolysis of trimethyl 2-[(carboxymethyl)oxy]succinate (E=30) and N-carboxymethylaspartate (E=9) exclusively at the most sterically hindered of the three ester groups (the position α to the asymmetric centre). Gram-scale resolution allowed the preparation of the less reactive trimethyl (S)-2-[(carboxymethyl)oxy]succinate (96% e.e.), that of the (R)-butyldimethyl regioisomer (78% e.e.) at 55% conversion and finally the preparation of the corresponding trisodium carboxylate by saponification. Acylase I was shown to transform (±)-methyl N-acetylmethionine and (±)-valine to the corresponding (S)-amino acids through ester hydrolysis-N-acetyl transfer sequence with absolute chemo- and enantioselectivity. Butanolysis of methyl N-acetylmethionine stopped in the formation of the butyl ester (E=12), the valine derivative being totally unreactive.