2-Iodoacetamide

ChemicalBook > CAS DataBase List > 2-Iodoacetamide

Product Name: 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
Formula Weight: 184.96
MOL File: 144-48-9.mol

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2-Iodoacetamide Property

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.
form: crystalline
pka: 15.16±0.40(Predicted)
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)
NIST Chemistry Reference: Alpha-iodo acetamide(144-48-9)
EPA Substance Registry System: 2-Iodoacetamide (144-48-9)

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Safety

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
F: 8-10-21
TSCA: T
HazardClass: 6.1
PackingGroup: III
HS Code: 29241900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 8.04744
Product name: 2-Iodoacetamide
Purity: for synthesis
Packaging: 25g
Price: $73.2
Updated: 2024/03/01

Sigma-Aldrich

Product number: 8.04744
Product name: 2-Iodoacetamide
Purity: for synthesis
Packaging: 100g
Price: $233
Updated: 2024/03/01

Sigma-Aldrich

Product number: A3221
Product name: Iodoacetamide
Purity: Single use vial of 56 mg
Packaging: 10vials
Price: $97.9
Updated: 2024/03/01

Sigma-Aldrich

Product number: 8.04744
Product name: 2-Iodoacetamide
Purity: for synthesis
Packaging: 1kg
Price: $1500
Updated: 2024/03/01

Sigma-Aldrich

Product number: 8.04744
Product name: 2-Iodoacetamide
Purity: for synthesis
Packaging: 2.5kg
Price: $3550
Updated: 2024/03/01

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2-Iodoacetamide Chemical Properties,Usage,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.

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.

2-Iodoacetamide Preparation Products And Raw materials

Raw materials

Dry acetone Acetone Chloroacetamide Sodium iodide

Preparation Products

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2-Iodoacetamide Suppliers

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View Lastest Price from 2-Iodoacetamide manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: 2-Iodoacetamide 144-48-9
Price: US $0.00-0.00/KG
Min. Order: 5mg
Purity: 99% HPLC
Supply Ability: 2000tons
Release date: 2019-12-30

Hebei Yanxi Chemical Co., Ltd.

Product: 2-Iodoacetamide 144-48-9
Price: US $0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 20 tons
Release date: 2023-11-21

Hebei Mojin Biotechnology Co., Ltd

Product: 2-Iodoacetamide 144-48-9
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-11-20

144-48-9, 2-IodoacetamideRelated Search:

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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