64-69-7 Usage
Chemical Properties
white to light yellow crystalline powder
Uses
Different sources of media describe the Uses of 64-69-7 differently. You can refer to the following data:
1. Used as a general reagent in acylation reactions. A byproduct formed in treated waters, and found in marine life.
2. Iodoacetic acid is used as a reagent for the modification of sulfhydryl groups in organic synthesis. It reacts with cysteine moiety in proteins to prevent the re-formation of disulfide bonds during protein sequencing. It is also used as a general reagent in acylation reactions as well as in glycopeptide synthesis.
Definition
ChEBI: A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom.
General Description
Colorless or white crystals.
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.
