101-29-1

Basic information

• Product Name: 3,5-DIIODO-4-PYRIDONE-1-ACETIC ACID
• Synonyms: 3,5-DIIODO-4-HYDROXYPYRIDINE-N-ACETIC ACID;3,5-DIIODO-4-PYRIDONE-1-ACETIC ACID;3,5-DIIODO-4-PYRIDONE-N-ACETIC ACID;3,5-DIIODO-4-OXO-1(4H)-PYRIDINEACETIC ACID;(3,5-DIIODO-4-OXO-4H-PYRIDIN-1-YL)-ACETIC ACID;1,4-DIHYDRO-3,5-DIIODO-4-OXO-1-PYRIDINEACETIC ACID;TIMTEC-BB SBB005882;1,4-dihydro-3,5-diiodo-4-oxo-1-pyridylacetic acid
• CAS NO: 101-29-1
• Molecular Formula: C₇H₅I₂NO₃
• Molecular Weight: 404.93
• EINECS: 202-932-5
• Mol File: 101-29-1.mol

Chemical Properties

• Melting Point: 244°C (dec.)
• Boiling Point: 422.8 °C at 760 mmHg
• Flash Point: 209.5 °C
• Appearance: /
• Density: 2.2000 (rough estimate)
• Vapor Pressure: 2.47E-08mmHg at 25°C
• Refractive Index: 1.7400 (estimate)
• PKA: 3.60±0.10(Predicted)
• Water Solubility: 2.787g/L(temperature not stated)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 3,5-DIIODO-4-PYRIDONE-1-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIIODO-4-PYRIDONE-1-ACETIC ACID(101-29-1)
• EPA Substance Registry System: 3,5-DIIODO-4-PYRIDONE-1-ACETIC ACID(101-29-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 101-29-1(Hazardous Substances Data)

Usage

Originator

Iodopyracet,Winthrop

Uses

3,5-Diiodo-4-pyridone-1-acetic Acid is used in contrast media.

Manufacturing Process

2 mol of pyridine are reacted with thionyl chloride to give 4-pyridyl-pyridinium chloride. The last one is transformed into 4-1H-pyridone by adding of water at 150°C. Then it is added to 1 mol of iodomonochloride (ICl) to give 3,5- diidopyridone. It is converted in 3.5-diiodo-4-pyridone-N-acetic acid by addition of chloroacetic acid and sodium hydrate. 1 mol of 3.5-diiodo-4- pyridone-N-acetic acid is dissolved in a solution of 1 mol of diethanolamine in 60 ml of water while heating. The solution is made up to 100 ml with water. After evaporating the solution and recrystallizing, the salt is obtained in the form of white crystals. MP: 153°C.

Therapeutic Function

Diagnostic aid

InChI:InChI=1/C7H5I2NO3/c8-4-1-10(3-6(11)12)2-5(9)7(4)13/h1-2H,3H2,(H,11,12)

Upstream product

• 101349-88-6 1-hydroxy-1H-pyridin-4-one 
• 41979-39-9 4-piperidone hydrochloride 
• 79-11-8 chloroacetic acid 
• 108-96-3 4-pyridone 
• 7153-08-4 4-hydroxy-3,5-diiodopyridine 

Relevant articles and documents

Preparation method of 3,5-dihalogenated-4-pyridone-1-acetic acid

The invention provides a preparation method of 3, 5-dihalogenated-4-pyridone-1-acetic acid, and particularly relates to a preparation method of 3,5-dichloro-4-pyridone-1-acetic acid. The method comprises the following steps: performing a substitution reaction on piperidine-4-ketone hydrochloride (II) with chloroacetic acid in the presence of a proper solvent and an acid-binding agent to obtain 4-piperidone-1-acetic acid (III), carrying out a halogenation reaction on the 4-piperidone-1-acetic acid (III) and a halogenation reagent to obtain 3,3,5,5-tetrahalogenated-4-piperidone-1-acetic acid (IV), carrying out an elimination reaction in the presence of an alkali to remove hydrogen halide, and performing acidification with hydrochloric acid to obtain the 3,5-dihalo-4-pyridinone-1-acetic acid.The method has the advantages of cheap and easily available raw materials, low cost, simple operation, easy realization, less wastewater generation amount, environmental protection, high reaction selectivity, high product yield and purity, and suitableness for industrial production.