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: 2023-09-01 16:14:28

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.