Iodoacetamide

Base Information

• Chemical Name: Iodoacetamide
• CAS No.: 144-48-9
• Molecular Formula: C2H4INO
• Molecular Weight: 184.964
• Hs Code.: 29241900
• European Community (EC) Number: 205-630-1
• NSC Number: 9581
• UNII: ZRH8M27S79
• DSSTox Substance ID: DTXSID9020742
• Nikkaji Number: J3.270K
• Wikipedia: Iodoacetamide
• Wikidata: Q2191895
• NCI Thesaurus Code: C161898
• Pharos Ligand ID: YTNWNC7HAMUP
• ChEMBL ID: CHEMBL276727
• Mol file: 144-48-9.mol

Synonyms:Iodoacetamide

Chemical Property of Iodoacetamide

Chemical Property:

• Appearance/Colour: yellow-brown crystals
• Melting Point: 92-95 °C(lit.)
• Boiling Point: 297.1 °C at 760 mmHg
• PKA: 15.16±0.40(Predicted)
• Flash Point: 133.5 °C
• Density: 2.278 g/cm³
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: 0.5 M at 20 °C, clear, colorless
• Water Solubility.: slightly soluble
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 184.93376
• Heavy Atom Count: 5
• Complexity: 44.9

Purity/Quality:

99% ^*data from raw suppliers

2-Iodoacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-42/43-43-36/37/38-53
• Safety Statements: 22-36/37-45-37/39-26-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C(C(=O)N)I
• 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.

Technology Process of Iodoacetamide

There total 9 articles about Iodoacetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cyanoacetic acid amide (107-91-5) → iodacetamide (144-48-9)

Guidance literature:

cyanoacetic acid amide; With hydrogenchloride; In water; N,N-dimethyl-formamide; for 48h; Reflux;

With dmap; iodine; potassium carbonate; In tetrahydrofuran; water; at 25 ℃;

DOI:10.1016/j.tet.2015.07.029

Reference yield:

iodoacetic anhydride (54907-61-8) → iodacetamide (144-48-9)

Guidance literature:

With triethylamine; In chloroform;

Reference yield:

Chloroacetamide (79-07-2) → iodacetamide (144-48-9)

Guidance literature:

With acetone; sodium iodide;

upstream raw materials:

Chloroacetamide

iodoacetonitrile

ethanol

iodoacetic anhydride

Downstream raw materials:

cysteine

Methylsulfonyloxy-acetamid

Diphenyl-dithiophosphinigsaeure-aminocarbonylmethylester

2-carbamoylmethylthio-6-methyl-4-phenyl-5-ethoxycarbonyl-3-cyano-1,4-dihydropyridine

Refernces

• 1、 Harland, Aubrie A.,Bender, Aaron M.,Griggs, Nicholas W.,Gao, Chao,Anand, Jessica P.,Pogozheva, Irina D.,Traynor, John R.,Jutkiewicz, Emily M.,Mosberg, Henry I.. "Effects of N-Substitutions on the Tetrahydroquinoline (THQ) Core of Mixed-Efficacy μ-Opioid Receptor (MOR)/δ-Opioid Receptor (DOR) Ligands". . p. 4985 - 4998. Retrieved 2016/06/13.
• 2、 -. "Reactive derivatives of sulforhodamine 101 with enhanced hydrolytic stability". . . Retrieved 2008/06/13.