Name | Iodoacetamide |
Synonyms | Surauto usafd-1 USAF d-1 2-Iodacetamid Iodoacetamide 2-iodo-acetamid 2-Iodoacetamide 2-Iodoacétamide Monoiodoacetamide Acetamide, 2-iodo- Iodiacetamide[IAM] |
CAS | 144-48-9 |
EINECS | 205-630-1 |
InChI | InChI=1/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5) |
InChIKey | PGLTVOMIXTUURA-UHFFFAOYSA-N |
Molecular Formula | C2H4INO |
Molar Mass | 184.96 |
Density | 2.1103 (estimate) |
Melting Point | 92-95°C(lit.) |
Boling Point | 297.1±23.0 °C(Predicted) |
Water Solubility | H2O: 0.5M at 20°C, clear, colorless |
Solubility | Soluble in hot water, easily soluble in ethanol. |
Appearance | White crystalline powder |
Color | White to pale yellow or beige |
BRN | 1739080 |
pKa | 15.16±0.40(Predicted) |
Storage Condition | 2-8°C |
Stability | Stable, but light sensitive. Incompatible with strong oxidizing agents, strong bases, reducing agents, acids. |
Sensitive | Light Sensitive |
MDL | MFCD00008028 |
Physical and Chemical Properties | White crystals. Melting point 95 °c. Soluble in hot water, soluble in ethanol. |
Use | For Organic synthesis |
Hazard Symbols | T - Toxic |
Risk Codes | R25 - Toxic if swallowed R42/43 - May cause sensitization by inhalation and skin contact. R43 - May cause sensitization by skin contact R36/37/38 - Irritating to eyes, respiratory system and skin. R53 - May cause long-term adverse effects in the aquatic environment |
Safety Description | S22 - Do not breathe dust. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24 - Avoid contact with skin. |
UN IDs | UN 2811 6.1/PG 3 |
WGK Germany | 3 |
RTECS | AC4200000 |
FLUKA BRAND F CODES | 8-10-21 |
TSCA | T |
HS Code | 29241900 |
Hazard Class | 6.1 |
Packing Group | III |
Reference Show more | 1. [IF=6.992] Zhang Chunlei et al."Serratia marcescens PLR enhances lateral root formation through supplying PLR-derived auxin and enhancing auxin biosynthesis in Arabidopsis."J Exp Bot. 2022 Feb;: |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Biological activity | 2-Iodoacetamide (Iodoacetamide) is a commonly used alkylating agent, commonly used in proteomics sample preparation process Cysteine alkylation. |
Animal Model: | Sprague-Dawley rats |
Dosage: | 2.0-10 mg |
Administration: | Drinking water, daily, for periods of 20 to 93 days |
Result: | Produced gastritis which was further complicated by chronic ulceration in many of the test rats. |
use | can be used as a protease inhibitor CH2ICONH2, like iodoacetic acid, can irreversibly inhibit SH enzymes through the following reactions. R-SH + ICH2CONH2 → R-S-CH2CONH2 + HI alkylation reagents of histidine and cysteine in proteomics are used for polypeptide sequencing and enzyme inhibitors. It is also used in organic synthesis. |
Production method | is obtained by the reaction of chloroacetamide and sodium iodide. 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 cooling, and then neutralize with sodium sulfate saturated solution to pH6. Cool the crystallization and filter to produce coarse products. The crude product is recrystallized with water to obtain the finished product. |