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2-Iodoacetamide

CAS No.
144-48-9
Chemical Name:
2-Iodoacetamide
Synonyms
IODOACETAMIDE;IAM;IODACETAMIDE;Surauto;usafd-1;USAF d-1;2-Iodacetamid;Iodoethanamide;2-iodo-acetamid;2-IODOACETAMIDE
CBNumber:
CB4760867
Molecular Formula:
C2H4INO
Molecular Weight:
184.96
MDL Number:
MFCD00008028
MOL File:
144-48-9.mol
MSDS File:
SDS
Last updated:2024-12-18 14:08:52

2-Iodoacetamide Properties

Melting point 92-95 °C(lit.)
Boiling point 297.1±23.0 °C(Predicted)
Density 2.1103 (estimate)
storage temp. 2-8°C
solubility Soluble in water, dimethyl formamide and ethanol. Slightly soluble in methanol.
pka 15.16±0.40(Predicted)
form crystalline
color White to pale yellow or beige
Water Solubility H2O: 0.5M at 20°C, clear, colorless
Sensitive Light Sensitive
BRN 1739080
Stability Stable, but light sensitive. Incompatible with strong oxidizing agents, strong bases, reducing agents, acids.
InChIKey PGLTVOMIXTUURA-UHFFFAOYSA-N
CAS DataBase Reference 144-48-9(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII ZRH8M27S79
NIST Chemistry Reference Alpha-iodo acetamide(144-48-9)
EPA Substance Registry System 2-Iodoacetamide (144-48-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H317-H334-H413
Precautionary statements  P261-P264-P273-P280-P301+P310-P302+P352
Hazard Codes  T
Risk Statements  25-42/43-43-36/37/38-53
Safety Statements  22-36/37-45-37/39-26-24
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  AC4200000
8-10-21
TSCA  T
HazardClass  6.1
PackingGroup  III
HS Code  29241900
NFPA 704
1
3 0

2-Iodoacetamide price More Price(50)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.04744 2-Iodoacetamide for synthesis 144-48-9 25g $73.2 2024-03-01 Buy
Sigma-Aldrich 8.04744 2-Iodoacetamide for synthesis 144-48-9 100g $233 2024-03-01 Buy
Sigma-Aldrich A3221 Iodoacetamide Single use vial of 56 mg 144-48-9 10vials $97.9 2024-03-01 Buy
Sigma-Aldrich 8.04744 2-Iodoacetamide for synthesis 144-48-9 1kg $1500 2024-03-01 Buy
Sigma-Aldrich 8.04744 2-Iodoacetamide for synthesis 144-48-9 2.5kg $3550 2024-03-01 Buy
Product number Packaging Price Buy
8.04744 25g $73.2 Buy
8.04744 100g $233 Buy
A3221 10vials $97.9 Buy
8.04744 1kg $1500 Buy
8.04744 2.5kg $3550 Buy

2-Iodoacetamide Chemical Properties,Uses,Production

Chemical Properties

White solid in amber, foil sealed microtubes. Soluble in hot water, easily soluble in ethanol.

Uses

2-Iodoacetamide is an alkylating reagent for cysteine residues in peptide sequencing. Its actions are similar to those of iodoacetate. By virtue of reaction with cysteine, it is an irreversible inhibitor of enzymes with cysteine at the active site. It reacts much more slowly with histidine residues, but that activity is responsible for inhibition of ribonuclease.

Application

Alkylating agent used in peptide mapping because it covalently binds with the thiols in cysteine to prevent disulfide bond formation 2-Iodoacetamide is used as an electrophile for covalent modification of nucleophilic residues on proteins such as cysteine, methionine and histidine. It is used to bind with thiol group of cysteine, thereby it protects the formation disulfide bonds. It is involved as an inhibitor of deubiquitinase enzymes (DUBs). Further, it acts as an alkylating sulfhydryl reagent.

Biological Activity

Iodoacetamide acts as an alkylating reagent for cysteine residues in peptide sequencing. It is an irreversible inhibitor of enzymes with cysteine at the active site. It reacts much more slowly with histidine residues, but that activity is responsible for inhibiting ribonuclease.

Synthesis

2-Iodoacetamide is synthesized by reacting chloroacetamide with sodium iodide. The chloroacetamide, anhydrous acetone, and anhydrous sodium iodide were refluxed on the bath for 15h. Cool to room temperature, filter out sodium chloride, recover acetone, pour into ice water of sodium bisulfate after a little cooling, and then neutralize to pH 6 with saturated sodium sulfate solution. Cool to crystallize and filter to obtain crude product. The crude product is recrystallized with water to obtain the finished product.

Purification Methods

Crystallise it from water or CCl4. It is used for tagging proteins. [Gurd Methods Enzymol 25 424 1972, Beilstein 2 IV 536.]

Preparation and handling

Alkylation Procedure
Iodoacetamide is unstable and light-sensitive. Prepare solutions immediately before use and perform alkylation in the dark. If iodoacetamide is present in limiting quantities and a slightly alkaline pH, cysteine modification will be the exclusive reaction. Excess iodoacetamide or non-buffered iodoacetamide reagent can also alkylate amines (lysine, N-termini), thioethers (methionine), imidazoles (histidine) and carboxylates (aspartate, glutamate).
1. Add 5 μl of 2% SDS and 45 μl of 200 mM ammonium bicarbonate (pH 8.0) to 20-100 μg of protein sample. Adjust volume to 100 μl with ultrapure water.
2. Add 5 μl of 200 mM Tris(2-carboxyethyl) phosphine hydrochloride (TCEP.HCl, Product No. 20490) and incubate sample at 55°C for 1 hour.
3. Immediately before use, dissolve one tube of iodoacetamide (9.3 mg) with 132 μl of 200 mM ammonium bicarbonate (pH 8.0) to make 375 mM iodoacetamide. Protect solution from light.
4. Add 5 μl of the 375 mM iodoacetamide to the sample and incubate for 30 minutes protected from light.
5. Proceed to proteolytic digestion before MS analysis or other processing.

Precautions

Store in a cool place. Light and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents.

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View Lastest Price from 2-Iodoacetamide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-Iodoacetamide   pictures 2024-12-25 2-Iodoacetamide
144-48-9
US $75.00-20.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
2-Iodoacetamide pictures 2024-11-19 2-Iodoacetamide
144-48-9
US $40.00 / mg ≥98% 10g TargetMol Chemicals Inc.
2-Iodoacetamide pictures 2024-11-05 2-Iodoacetamide
144-48-9
US $0.00-0.00 / KG 5mg 99% HPLC 2000tons Shaanxi Dideu Medichem Co. Ltd
  • 2-Iodoacetamide   pictures
  • 2-Iodoacetamide
    144-48-9
  • US $75.00-20.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
  • 2-Iodoacetamide pictures
  • 2-Iodoacetamide
    144-48-9
  • US $0.00-0.00 / KG
  • 99% HPLC
  • Shaanxi Dideu Medichem Co. Ltd
2-iodo-acetamid Acetamide, 2-iodo- Monoiodoacetamide Surauto USAF d-1 usafd-1 2-Iodoacetamide, Stab. With ca 5-8% Water Iodiacetamide[IAM] 2-IodoacetaMide  IodoacetaMide, 98% 25GR 2-IODOACETAMIDE FOR SYNTHESIS 2-IodoacetaMide, 98.0%(N) IAM, iodoacetamide Iodoacetamide 2-Iodoacetamide Iodoacetamide Vetec(TM) reagent grade, 99% COLUMN HIBIND RNA COLUMNS Iodoacetamide acid IODOACETAMIDE BIOULTRA IODOACETAMIDE, >=99% (NMR), CRYSTALL IODOACETAMIDE, SINGLE USE VIAL OF 56 2-Iodoacetamide, stabilized with &ap:5 to 8% water ALPHA-IODOACETAMIDE 2-IODOACETAMIDE 0IODOACETAMIDE CRYSTALLINE ALKYLATING REAGENT, IODOACETAMIDE IODOACETAMIDE SIGMAULTRA 2-Iodoacetamide, 98%, stab. with ca 5-8% water 2-IODOACETAMIDE,CRYSTAL Iodoethanamide 2-Iodoacetamide [for Biochemical Research] Iodoacetamide,98% α-Iodoacetamide - CAS 144-48-9 - Calbiochem 2-Iodacetamid Iodoacetamide, 98%, reagent grade 2-Iodoacetamide[forBiochemicalResearch]> 2-Iodoacetamide> 2-Iodoacetamide ISO 9001:2015 REACH IAM IODOACETAMIDE IODACETAMIDE 2-lodoacetamide 144-48-9 C2H4INO C2H4I1N1O1 ICH2CONH2 BioChemical Biochemicals and Reagents A to C Carnitine acetyltransferase Protein Modification Specific Amino Acid Modification Enzymes, Inhibitors, and Substrates Enzyme Inhibitors by Enzyme Enzyme Inhibitors Reagents for cysteine modification Proteomics and Protein Expression Proteomics API intermediates