64-69-7

Usage

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.]

InChI:InChI=1/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)/p-1

Upstream product

• 38020-81-4 2-iodoacetyl chloride 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 79-08-3 bromoacetic acid 
• 79-11-8 chloroacetic acid 
• 623-48-3 ethyl iodoacetae 
• 7553-56-2 iodine 
• 7782-68-5 iodic acid 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 67-64-1 acetone 
• 7732-18-5 water 
• 563-80-4 3-methyl-butan-2-one 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 89166-38-1 1,4-diiodo-butane-2,3-diol 

Downstream Products

• 83004-93-7 iodo-acetic acid propyl ester 
• 70648-87-2 thioglycolic acid monoanilide 
• 75-11-6 diiodomethane 
• 38020-81-4 2-iodoacetyl chloride 
• 54907-61-8 iodoacetic anhydride 
• 123-93-3 thiodiacetic acid 
• 505-73-7 disulfanediyldiacetic acid 
• 150-25-4 N,N-bis-(2-hydroxyethyl)glycine 
• 139-13-9 nitrilotriacetic acid 
• 80935-06-4 phenyl α-iodoacetate 
• 55572-13-9 Jodessigsaeure-pentachlorphenylester 
• 55030-41-6 trimethylsilyl iodoacetate 
• 63984-18-9 N-Iodacetylglycinbenzylester 
• 63984-19-0 N-Iodacetyl-β-aminopropionsaeurebenzylester 

Relevant academic research and scientific papers

Effect of ionic crosslinking on the drug release properties of chitosan diacetate matrices

Chitosan diacetate (CDA) was prepared by alkylating the amino moieties of chitosan with mono-iodoacetic acid. Subsequently, CDA was cross-linked with Al3+, Zn2+, and Ca2+ ions to yield three ionotropically crosslinked polymeric matrices. These composite matrices were characterized employing infrared spectroscopy (IR) and differential scanning calorimetry (DSC). Subsequently, they were loaded with caffeine, as a model drug, and were assessed as sustained release carriers by evaluating their caffeine release profiles. Interestingly, only CDA-Zn2+ complex sustained the release of caffeine effectively in a zero-order manner. The drug release and thermal behavior of the tested matrices agree with the relative strength of the ionic or coordination character of the bonds. This, in turn, depends on the position of the complexing ions on the electrophilic softness/hardness scale.

A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids

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.).

METHODS OF TREATING PAIN

The present invention is directed to methods and compositions for inducing, promoting or otherwise facilitating pain relief. More particularly the present invention discloses the combination of a nitric oxide donor and an opioid analgesic in the therapeutic management of vertebrate animals including humans, for the prevention or alleviation of pain, particularly moderate to severe pain. In particular, the nitric oxide donor is a slow-release nitric oxide donor or is formulated to provide a sustained release of a low dose of nitric oxide.

Thermolysis of alkoxyaluminum and siloxyaluminum acylates

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.

Synthesis and thermal decomposition of derivatives of acyloxytetraphenylantimony

Acyloxy derivatives of tetraphenylantimony of the general formula Ph4SbOC(O)R (R = Alk or Ar) have been synthesized by the reaction of pentaphenylantimony with carboxylic acids. Thermolysis of the compounds obtained affords phenyl carboxylates and triphenylstibine in quantitative yields. One of these compounds (R = CH=CHPh) has been studied by X-ray structural analysis. In this compound, the Sb atom has a trigonal-bipyramidal coordination. The Sb-O(Ph)eq distances are in the range 2.103(4)-2.140(5) A; the Sb-C(Ph)ax bond length is 2.167(5) A. The fragment of the residue of cinnamic acid has a delocalized double bond in the carboxylate group.

Macrolide immunomodulators

Novel macrolide compounds of the formula STR1 and pharmaceutically acceptable salts, esters, amides and prodrugs thereof, processes for the preparation of the compounds of the invention, intermediates useful in these processes, a pharmaceutical composition, and a method of treating immunomodulatory disorders are disclosed.

Macrocyclic amide and urea immunomodulators

Immunomodulatory macrocyclic compounds having the formula: STR1 and pharmaceutically-acceptable salts, esters, amides and prodrugs thereof, as well as pharmaceutical compositions containing the same, which possess immunosuppressive, antimicrobial, antifungal, antiviral, antiinflammatory and antiproliferative activity, as well as the ability to reverse chemotherapeutic drug resistance.

Reactions of nucleophilic substitution involving solid organic halogen compounds under shear deformation at high pressure

Under conditions of shear deformation and high pressures (SD + HP), reactions of nucleophilic substitution were studied: 1) the replacement of aliphatic halogen atom with alkaline metal halides (halo-substituted aliphatic carboxylic acids, 1-bromoadamantane); 2) the replacement of halogen atom in aromatic nucleus (halobenzoic acids, dihalobenzenes) with halogen of salt; 3) the replacement of aliphatic halogen with hydroxyl (hydrolysis in a solid phase); 4) the replacement of halogen with amino group under deformation of the samples of ammonium α-halocarboxylates to give the corresponding amino acids.It was found that the exchange of the halogen atoms bonded with aliphatic carbon is most intensive in the mixtures of alkaline metal iodides with bromo-substituted acetic acid and propionic acids: the exchange reaction in these mixtures is observed even during grinding in the mortar. Unlike the liquid phase, under conditions of SD + HP exchange of the halogen atom of the aromatic nucleus with alkaline metal halides, proceeds successfully, and the reactivity of halides increases in the series Na K Rb Cs.Under SD + HP, 1-Br-adamantane reacts with water to form 1-adamantanol.A high reactivity of the water adsorbed by the reagents is observed. - Key words: shear deformation, high pressure, halogen derivatives of carboxylic acids, dihalobenzenes, alkaline metal halides, ammonium salts of halogen derivatives of carboxylic acids, amino acids, halo-substituted adamantanes, adamantanol, nucleophilic substitution reaction, hydrolysis, ball mill.

A New Microwave Reactor for Batchwise Organic Synthesis

A laboratory-scale microwave batch reactor (MBR) has been developed for organic synthesis or kinetic studies on the 20-100 mL scale, with upper operating limits of 260 deg C and 10 MPa (100 atm).The MBR complements a continuous microwave reactor which was the subject of a previous report from the author's laboratory.Microwave-assisted organic reactions were conducted safely and conveniently in the MBR, for lengthy periods when required, and in volatile organic solvents.The use of water as a solvent for organic reactions was also explored.Examples include oxidation, elimination, esterifications, hydrolysis of a tertiary amide, etherification, isomerization, Hofmann elimination, α-iodination of a carboxylic acid, Claisen rearrangement, aminoreductone formation, and Willgerodt reactions.Advantages of the new MBR include the capability for rapid heating and quenching of reaction mixtures, minimal temperature gradients within the sample, and elimination of wall effects.Safety aspects have been discussed.

HETEROCYCLIC HYDRAZIDE DERIVATIVES OF MONOCYCLIC BETA-LACTAM ANTIBIOTICS

Antibacterial activity has been found in compounds of the formula. Compounds having the formula and pharmaceutically acceptable salts thereof, wherein: A is a bond or alkylene; Q completes a 5- or 6-membered saturated or unsaturated(including aromatic) heterocyclic ring having one or two, hetero atoms in the ring selected from nitrogen sulfur or oxygen; X is attached to an available carbon atom in the heterocyclic ring and is hydrogen or oxo; Y is attached to an available carbon atom in the heterocyclic ring and is hydrogen, amino, hydroxyl, halogen, carboxamide, nitrile, or carboxyl, except that Y is not carboxyl when the bicyclic ring completed by Q is 2-quinolyl, 3-quinolyl, or quinoxalyl; and the remaining symbols are as defined in the specification