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

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

Downstream Products

• 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 
• 38953-72-9 5-iodo-2,4-bis-O-trimethylsilyluracil 
• 1198745-16-2 5-iodo-2-[((1R)-1-methyl-2-{3-[(1-methylethyl)oxy]phenyl}ethyl)oxy]pyrimidine 
• 83768-03-0 1-(4-chlorophenoxy)methyl-5-iodopyrimidin-2-one 
• 116392-93-9 5-iodo-12-phenylsulfenylmethyl-2(1H)-pyrimidinone 
• 83768-02-9 2-(4-chlorophenoxy)methoxy-5-iodopyrimidine 
• 116392-90-6 5-iodo-1-phenoxymethyl-2(1H)-pyrimidinone 
• 116519-90-5 1-benzyloxymethyl-5-iodo-2(1H)-pyrimidinone 
• 103594-69-0 1-benzyl-5-iodopyrimidin-2-(1H)-one 

Relevant articles and documents

Preparation method of 1-(2-deoxy-beta-D-ribofuranose)-5-iodo-2-pyrimidone

The invention relates to 1-(2-deoxidized-beta-D-ribofuranose)-5-iodo-2-pyrimidone, and particularly relates to a preparation method of 1-(2-deoxidized-beta-D-ribofuranose)-5-iodo-2-pyrimidone. The preparation method comprises the following steps of performing a reaction on 2-hydroxypyrimidine hydrochloride and a glacial acetic acid/iodine monochloride solution so as to generate 5-iodo-2-pyrimidone; performing a reaction on the 5-iodo-2-pyrimidone and 1-chloro-3,5-di(4-chlorbenzoyl)-2-deoxy-D-ribose so as to generate 1-[(3,5-di(4-chlorbenzoyl)-2-deoxy-beta-D-erythro-pentofuranose]-5-iodo-2-pyrimidone; and finally generating a target product by using the 1-[(3,5-di(4-chlorbenzoyl)-2-deoxy-beta-D-erythro-pentofuranose]-5-iodo-2-pyrimidone. All intermediates are stable, the yield is high, andthe method is suitable for industrial production.

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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