Iodoacetic acid

Base Information

• Chemical Name: Iodoacetic acid
• CAS No.: 64-69-7
• Molecular Formula: C2H3IO2
• Molecular Weight: 185.949
• Hs Code.: 29159080
• European Community (EC) Number: 200-590-1
• NSC Number: 2125
• UN Number: 1759
• UNII: WF5188V710
• DSSTox Substance ID: DTXSID5025445
• Nikkaji Number: J1.405B
• Wikipedia: Iodoacetic_acid
• Wikidata: Q416375
• Metabolomics Workbench ID: 1821
• ChEMBL ID: CHEMBL376280
• Mol file: 64-69-7.mol

Synonyms:Acid, Iodoacetic;Acid, Monoiodoacetic;Iodoacetate, Monosodium;Iodoacetate, Sodium;Iodoacetic Acid;Monoiodoacetic Acid;Monosodium Iodoacetate;Sodium Iodoacetate

Chemical Property of Iodoacetic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 0.00329mmHg at 25°C
• Melting Point: 79-83 °C
• Boiling Point: 262.102 °C at 760 mmHg
• PKA: 3.12(at 25℃)
• Flash Point: 112.316 °C
• PSA: 37.30000
• Density: 2.479 g/cm³
• LogP: 0.50600
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: soluble, clear to hazy
• Water Solubility.: 600 g/L (20 ºC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 185.91778
• Heavy Atom Count: 5
• Complexity: 42.9
• Transport DOT Label: Corrosive

Purity/Quality:

97%, ^*data from raw suppliers

Iodoacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, C
• Hazard Codes: T,C
• Statements: 25-35
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(=O)O)I
• Recent ClinicalTrials: Idarubicin Plus Cytarabine (IA) vs IA Plus Cladribine (IAC) as Induction Regimen to Treat Initially Diagnosed Acute Myeloid Leukemia (AML)
• Uses: Used as a general reagent in acylation reactions. A byproduct formed in treated waters, and found in marine life. 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.

Technology Process of Iodoacetic acid

There total 23 articles about Iodoacetic acid 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: 99.0%

Sb(C6H5)4(OOCCH2I) (177481-72-0) → tetraphenylantimony(V) chloride (19638-17-6,16894-68-1) + Iodoacetic acid (64-69-7)

Guidance literature:

With aq. HCl;

DOI:10.1007/BF01433760

Reference yield: 97.0%

diiodomethane (75-11-6) + carbon dioxide (124-38-9,18923-20-1) → Iodoacetic acid (64-69-7)

Guidance literature:

diiodomethane; With isopropylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 0.0166667h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1002/adsc.201801614

Reference yield: 95.0%

acetic acid (64-19-7,77671-22-8) → Iodoacetic acid (64-69-7)

Guidance literature:

With iodine; for 6h; Heating; var. reag.: CuCl₂, CuCl, CuOAc, Cu(OAc)2; var. time;

DOI:10.1246/cl.1984.1509

upstream raw materials:

2-iodoacetyl chloride

acetic anhydride

acetic acid

bromoacetic acid

Downstream raw materials:

iodo-acetic acid propyl ester

carbocisteine

thioglycolic acid monoanilide

diiodomethane

Refernces

• 1、 Aiedeh, Khaled M.,Taha, Mutasem O.,Al-Hiari, Yusuf,Bustanji, Yasser,Alkhatib, Hatim S.. "Effect of ionic crosslinking on the drug release properties of chitosan diacetate matrices". . p. 38 - 43. Retrieved 2007.
• 2、 -. "METHODS OF TREATING PAIN". Page/Page column 35. . Retrieved 2008/06/13.