79387-69-2

Basic information

• Product Name: 5-Iodo-2-pyrimidone
• Synonyms: 2-Hydroxy-5-Iodopyrimidine;2(1H)-Pyrimidinone, 5-iodo-;5-IodopyriMidin-2(1H)-one;5-iodo-1H-pyrimidin-2-one;5-Iodopyrimidin-2(1H);5-Iodo-2-pyrimidone
• CAS NO: 79387-69-2
• Molecular Formula: C₄H₃IN₂O
• Molecular Weight: 221.98
• Mol File: 79387-69-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 393.6ºC at 760 mmHg
• Flash Point: 191.8ºC
• Appearance: /
• Density: 2.403g/cm3
• Vapor Pressure: 9.28E-07mmHg at 25°C
• Refractive Index: 1.761
• Storage Temp.: 2-8°C(protect from light)
• PKA: 7.86±0.10(Predicted)
• CAS DataBase Reference: 5-Iodo-2-pyrimidone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Iodo-2-pyrimidone(79387-69-2)
• EPA Substance Registry System: 5-Iodo-2-pyrimidone(79387-69-2)

Safety Data

• Hazardous Substances Data: 79387-69-2(Hazardous Substances Data)

Usage

General Description

5-Iodo-2-pyrimidone, also known as 5-Iodo-2-pyrimidinol, is a chemical compound with the molecular formula C4H3IN2O. It is a derivative of pyrimidone, a heterocyclic organic compound. This chemical is primarily used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used in the production of dyes and pigments. 5-Iodo-2-pyrimidone exhibits potential anti-bacterial properties and has been the subject of research for its potential use in drug development. It is a white to off-white crystalline powder that is soluble in organic solvents such as ethanol and methanol. Overall, 5-Iodo-2-pyrimidone is a versatile chemical compound with potential applications in various industries.

InChI:InChI=1/C4H3IN2O/c5-3-1-6-4(8)7-2-3/h1-2H,(H,6,7,8)

Synthetic route

2-hydroxypyrimidine hydrochloride (38353-09-2) → 5-iodo-2(1H)-pyrimidinone (79387-69-2)

Conditions	Yield
With methanol; iodine; silver sulfate at 20℃; for 16h; Darkness;	94%

Pyrimidin-2(1H)-one (557-01-7) → 5-iodo-2(1H)-pyrimidinone (79387-69-2)

Conditions	Yield
With N-iodo-succinimide In N,N-dimethyl-formamide for 48h; Ambient temperature;	77.5%
With N-iodo-succinimide In N,N-dimethyl-formamide	11.35 g (77.5%)
With N-iodo-succinimide In N,N-dimethyl-formamide	11.35 g (77.5%)

2-pyrimidinone hydrochloride (38353-09-2) → 5-iodo-2(1H)-pyrimidinone (79387-69-2)

Conditions	Yield
With sodium dihydrogen phosphate; sodium iodine dichloride In water at 65℃; for 1.66667h;	75%
With Iodine monochloride; sodium chloride In water at 60℃; for 1h;
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 48h;
With Iodine monochloride; acetic acid In water at 45 - 48℃; for 6h; Temperature;

Upstream product

• 557-01-7 Pyrimidin-2(1H)-one 
• 38353-09-2 2-pyrimidinone hydrochloride 
• 38353-09-2 2-hydroxypyrimidine hydrochloride 

Downstream Products

• 103594-69-0 1-benzyl-5-iodopyrimidin-2-(1H)-one 
• 116519-90-5 1-benzyloxymethyl-5-iodo-2(1H)-pyrimidinone 
• 116392-90-6 5-iodo-1-phenoxymethyl-2(1H)-pyrimidinone 
• 83768-02-9 2-(4-chlorophenoxy)methoxy-5-iodopyrimidine 
• 83768-03-0 1-(4-chlorophenoxy)methyl-5-iodopyrimidin-2-one 
• 116392-93-9 5-iodo-12-phenylsulfenylmethyl-2(1H)-pyrimidinone 
• 1198745-16-2 5-iodo-2-[((1R)-1-methyl-2-{3-[(1-methylethyl)oxy]phenyl}ethyl)oxy]pyrimidine 
• 38953-72-9 5-iodo-2,4-bis-O-trimethylsilyluracil 
• 32779-38-7 2-chloro-5-iodopyrimidine 
• 96245-84-0 1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl>-5-iodo-2-pyrimidinone 

Relevant articles and documents

IDOXURIDINE AND ITS ANALOGS AS NEUROPROTECTANS FOR THE TREATMENT OF PARKINSONISM

The invention relates to compounds that are useful in the treatment of parkinsonism, such as parkinsonism in connection with Parkinson's disease (PD); dementia with Lewy bodies (DLB); multiple system atrophy (MSA); corticobasal degeneration (CBD); or progressive supranuclear palsy (PSP). The said compounds include in particular idoxuridineand analogs thereofas well as their metabolic precursors, such as ropidoxuridine.The invention further relates to method for identifying compounds useful for the treatment of parkinsonism, said methods comprising detecting the capability of compound to increase the amount of GPR37 in cell membranes.The invention further relates to methods for the chemical synthesis of ropidoxuridine.

Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling

α-Pyrones and pyrimidones are common structural motifs in natural products and bioactive compounds. They also display photochemistry that generates high-energy intermediates that may be capable of protein reactivity. A library of pyrones and pyrimidones was synthesized, and their potential to act as photoaffinity probes for nondirected affinity-based protein profiling in several crude cell lysates was evaluated. Further "proof-of-principle" experiments demonstrate that a pyrimidone tag on an appropriate scaffold is equally capable of proteome labeling as a benzophenone.

1-(2-Deoxy-b-D-ribofuranosyl)-5-iodo-2-pyrimidinone antiviral with low host cell toxicity.

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