64-69-7 Usage
Description
Iodoacetic acid, also known as 2-iodoethanoic acid, is an organoiodine compound with the chemical formula C2H4IO2. It is a colorless crystalline solid that is soluble in water and has a strong, pungent odor. Iodoacetic acid is a reagent used in various chemical reactions and has applications in different industries.
Uses
Used in Organic Synthesis:
Iodoacetic acid is used as a reagent for the modification of sulfhydryl groups in organic synthesis. It reacts with the cysteine moiety in proteins to prevent the re-formation of disulfide bonds during protein sequencing, which is essential for the proper analysis and identification of protein structures.
Used in Acylation Reactions:
Iodoacetic acid is also used as a general reagent in acylation reactions, where it helps in the transfer of acyl groups to other molecules, facilitating the formation of new chemical bonds and compounds.
Used in Glycopeptide Synthesis:
In the field of glycopeptide synthesis, iodoacetic acid plays a crucial role as a reagent. It aids in the formation of glycosidic bonds between carbohydrates and peptides, which are vital for the development of bioactive molecules with potential pharmaceutical applications.
Used in Water Treatment:
Iodoacetic acid is a byproduct formed in treated waters and can be found in marine life. It has potential applications in water treatment processes, where it may be used to control the growth of microorganisms and improve water quality.
Air & Water Reactions
May be sensitive to heat, light, and air. Water soluble
Reactivity Profile
Iodoacetic acid reacts vigorously with bases and is corrosive.
Fire Hazard
Flash point data for Iodoacetic acid are not available, but Iodoacetic acid is probably non-flammable.
Biochem/physiol Actions
Iodoacetic acid (IAA) blocks the thiol group of cysteine. IAA inhibits glyceraldehyde-3-phosphate dehydrogenase (G3PDH) by interacting with sulfhydryl group of the active site cysteine. IAA inhibits the progression of solid Ehrlich carcinoma. IAA is one of the iodinated disinfection byproducts in drinking water. It is cytotoxic to mammalian cells.
Purification Methods
Crystallise it from pet ether (b 60-80o) or CHCl3/CCl4. [Beilstein 2 IV 534.]
Check Digit Verification of cas no
The CAS Registry Mumber 64-69-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 4 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 64-69:
(4*6)+(3*4)+(2*6)+(1*9)=57
57 % 10 = 7
So 64-69-7 is a valid CAS Registry Number.
InChI:InChI=1/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)/p-1
64-69-7Relevant articles and documents
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Nessmejanow,Lutzenko
, (1945)
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A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids
Monticelli, Serena,Urban, Ernst,Langer, Thierry,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 1001 - 1006 (2019/01/30)
The homologation of carbon dioxide with stable, (enantiopure) magnesium carbenoids constitutes a valuable method for preparing α-halo acid derivatives. The tactic features a high level of chemocontrol, thus enabling the synthesis of variously functionalized analogues. The flexibility to generate magnesium carbenoids through sulfoxide-, halogen- or proton- Mg exchange accounts for the wide scope of the reaction. (Figure presented.).
Thermolysis of alkoxyaluminum and siloxyaluminum acylates
Stepovik,Kazakina,Martynova
, p. 1371 - 1377 (2007/10/03)
Thermolysis of alkoxyaluminum acylates (RO)nAl(OCORt)3-n (n = 1, 2; R = i-Pr, s-Bu, t-Bu, Rt = Ph, CH2I; R = PhCH2, Rt = Me, Et, Ph; R = Me3Si, Et3Si, Rt = Me) was studied. The main direction of thermolysis of derivatives of primary and secondary alcohols and of unsubstituted carboxylic acids is ester and alcohol formation. Trialkylsiloxyaluminum acylates termolyze to give in the first stage no other products than trialkylacyloxysilanes. Thermolysis of iodoacylates (RO)2AlOCOCH2I (R = Pr, s-Bu) involves oxidation of the alkoxy group to carbonyl compounds with simultaneous formation of a ketene and hydrogen iodide. tert-Butoxyaluminum acylates regardless of the structure of substituent in the acyloxy group undergo symmetrization to aluminum tert-butylate.