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HomeProduct name listIodoacetic acid

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: 2024-11-18 17:01:59
Iodoacetic acid Structural

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)
ghs
Corrosion
Corrosives
GHS05
ghs
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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