Iodoacetic acid
- CAS NO.:64-69-7
- Empirical Formula: C2H3IO2
- Molecular Weight: 185.95
- MDL number: MFCD00002685
- EINECS: 200-590-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-09-25 09:23:02
What is Iodoacetic acid?
Chemical properties
white to light yellow crystalline powder
The Uses of Iodoacetic acid
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.
The Uses of Iodoacetic acid
Used as a general reagent in acylation reactions. A byproduct formed in treated waters, and found in marine life.
What are the applications of Application
Iodoacetic acid is a reagent useful for modifying cysteine residues
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.]
Properties of Iodoacetic acid
Melting point: | 79 °C |
Boiling point: | 208°C |
Density | 2.2003 (estimate) |
Flash point: | 208°C |
storage temp. | 2-8°C |
solubility | H2O: soluble, clear to hazy |
form | Liquid |
pka | 3.12(at 25℃) |
color | faintly yellow |
Water Solubility | 600 g/L (20 ºC) |
Sensitive | Light Sensitive |
Merck | 14,5025 |
BRN | 1739079 |
Stability: | Stable. Incompatible with strong oxidizing agents, bases, strong reducing agents. Store at -20 C. |
CAS DataBase Reference | 64-69-7(CAS DataBase Reference) |
NIST Chemistry Reference | Acetic acid, iodo-(64-69-7) |
EPA Substance Registry System | Iodoacetic acid (64-69-7) |
Safety information for Iodoacetic acid
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H301:Acute toxicity,oral H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P260:Do not breathe dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
Computed Descriptors for Iodoacetic acid
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