155-12-4

Basic information

• Product Name: 2-CHLORO-5-FLUOROPYRIMIDIN-4-ONE
• Synonyms: 2-CHLORO-5-FLUOROPYRIMIDIN-4-ONE;2-Chloro-5-fluoro-pyrimidin-4-ol;4(1H)-Pyrimidinone, 2-chloro-5-fluoro- (9CI);2-Chloro-4-hydroxy-5-fluoropyrimidine;2-chloro-5-fluoro-1H-pyrimidin-6-one;4(3H)-Pyrimidinone, 2-chloro-5-fluoro-;2-chloro-5-fluoro-4-hydroxypyrimidine;2-Chloro-5-fluoro-3H-pyriMidin-4-one
• CAS NO: 155-12-4
• Molecular Formula: C₄H₂ClFN₂O
• Molecular Weight: 148.5228832
• Product Categories: PYRIMIDINE
• Mol File: 155-12-4.mol

Chemical Properties

• Melting Point: 176-177 °C(Solv: ethanol (64-17-5))
• Boiling Point: 178.5 °C at 760 mmHg
• Flash Point: 61.8 °C
• Appearance: /
• Density: 1.706 g/cm³
• Vapor Pressure: 0.985mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.48±0.50(Predicted)
• CAS DataBase Reference: 2-CHLORO-5-FLUOROPYRIMIDIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5-FLUOROPYRIMIDIN-4-ONE(155-12-4)
• EPA Substance Registry System: 2-CHLORO-5-FLUOROPYRIMIDIN-4-ONE(155-12-4)

Safety Data

• Hazardous Substances Data: 155-12-4(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry Research:
2-Chloro-5-fluoropyrimidin-4-one is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structural features allow for the development of new drugs with improved therapeutic properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-5-fluoropyrimidin-4-one serves as a building block for the creation of novel therapeutic agents. Its potential biological or pharmacological activities make it a valuable compound for the design and synthesis of new drugs with targeted effects on specific diseases or conditions.
Used in Organic Chemistry Research:
2-Chloro-5-fluoropyrimidin-4-one is also employed in organic chemistry research to explore its reactivity and potential use in the formation of new chemical entities. Its presence in the pyrimidine family provides a foundation for studying its interactions with other molecules and its role in various chemical reactions.

InChI:InChI=1/C4H2ClFN2O/c5-4-7-1-2(6)3(9)8-4/h1H,(H,7,8,9)

Upstream product

• 2927-71-1 2,4-dichloro-5-fluoropyrimidine 
• 51-21-8 5-fluorouracil 

Downstream Products

• 63650-58-8 2-benzyloxy-5-fluoro-3H-pyrimidin-4-one 
• 63650-55-5 2-n-Hexyloxy-5-fluoropyrimidin-4-one 
• 63650-49-7 2-butoxy-5-fluoro-4(1H)-pyrimidone 
• 63650-49-7 2-butoxy-5-fluoropyrimidine-4(3H)-one 

Relevant articles and documents

Tautomerism of 5-fluoro-4-hydroxy-2-methoxypyrimidine. Conditions for stabilization of the zwitterionic tautomer

5-Fluoro-4-hydroxy-2-methoxypyrimidine exists in a solution as two oxo tautomers with the conjugated and isolated double bonds in the ring. The latter tautomer has a zwitterionic structure, and it dominates in water and trifluoroethanol. 5-Fluoro-4-hydroxy-2-methoxypyrimidine in acidic medium gives rise to an equilibrium mixture of two protonated forms at a ratio of about ～1:1. The zwitterionic structure of 4-hydroxypyrimidines is stabilized if the solvent is capable for specific solvation via hydrogen bonding. Pleiades Publishing, Inc., 2006.

Coupling of DNA circuit and templated reactions for quadratic amplification and release of functional molecules

DNA-based circuitry empowers logic gated operations and amplifications but is restricted to nucleic acid output. Templated reactions enable the translation of nucleic acid cues into diverse small-molecule outputs but are more limited in their amplification. Herein, we demonstrate the coupling of a DNA circuit to templated reactions in order to achieve high levels of amplification in the output of small molecules, in response to nucleic acid input. We demonstrate that the coupling of the DNA circuit to templated reactions allows for the detection of the fM concentration of analyte and can respond with the release of a cytotoxic drug.

6-MEMBERED HETEROCYCLIC DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

A compound represented by Formula (I): wherein or the like Y1 is O or the like; Z1 is C(R4) or N; Z2a is C(R5a) or the like; Z3a is C(R6) or the like; R4, R5a and R6 are each independently a hydrogen atom or the like; R1 is substituted or unsubstituted aromatic carbocyclyl or the like; R2a, R2b, R2c and R2d are each independently a hydrogen atom or the like; X is N(R7a) or the like; R7a is a hydrogen atom or the like; R3 is or the like Ring B is a 6-membered aromatic carbocycle or the like; R9a and R10a are each independently halogen or the like; n is an integer from 1 to 5; m is an integer from 0 to 4; and p1 is an integer from 0 to 3, or a pharmaceutically acceptable salt thereof.

Development of matrix metalloproteinase-13 inhibitors – A structure-activity/structure-property relationship study

A structure-activity/structure-property relationship study based on the physicochemical as well as in vitro pharmacokinetic properties of a first generation matrix metalloproteinase (MMP)-13 inhibitor (2) was undertaken. After systematic variation of inhi

5-fluoro-uracil immunoassay

Novel conjugates of 5-fluoro-uracil and novel 5-fluoro-uracil immunogens and monoclonal antibodies generated by these immunogens which are useful in immunoassays for the quantification and monitoring of 5-fluoro-uracil in biological fluids.

Novel 5-fluorouracil derivatives: Synthesis and cytotoxic activity of 2-butoxy-4-substituted 5-fluoropyrimidines

Twenty two new 5-fluorouracil (5-FU) derivatives, 2-butoxy-4-substituted 5-fluoropyrimidines, were synthesized and characterized by IR, 1H NMR, MS, HRMS. All compounds were preliminarily evaluated by MTT assay on human liver BEL-7402 cancer cell line in vitro. Ten compounds were selected to test their cytotoxic activity against A549, HL-60 and MCF-7 cancer cell lines in vitro. These compounds were more sensitive to BEL-7402 than other cell lines, particularly, cytotoxic activity of compounds 6b, 6d-f, 6p, 6s-u were in sub-micromolar scale. The highest cytotoxic potency against A549, HL-60 and MCF-7 was shown by 2-butoxy-4-chloro-5- fluoropyrimidine (5) with IC 50 values of 0.10, 1.66 and 0.59 μM, respectively. Compounds 6d and 6e were effective against MCF-7 with IC50 9.73 μM and HL-60 with IC50 8.83 μM, respectively.

Design and synthesis of pyrimidinone and pyrimidinedione inhibitors of dipeptidyl peptidase IV

The discovery of two classes of heterocyclic dipeptidyl peptidase IV (DPP-4) inhibitors, pyrimidinones and pyrimidinediones, is described. After a single oral dose, these potent, selective, and noncovalent inhibitors provide sustained reduction of plasma DPP-4 activity and lowering of blood glucose in animal models of diabetes. Compounds 13a, 27b, and 27j were selected for development.

POLYMORPHS OF TARTRATE SALT OF 2-[2-(3-(R)-AMINO-PIPERIDIN-1-YL)-5-FLUORO-6-OXO-6H-PYRIMIDIN-1-YLMETHYL]-BENZONITRILE AND METHODS OF USE THEREFOR

Compositions comprising Compound I, wherein the Compound I is present in one or more polymorphic forms. Also provided are kits and articles of manufacture with compositions comprising one or more polymorphs of Compound I, and methods of using the compositions to treat various diseases.

ADMINISTRATION OF DIPEPTIDYL PEPTIDASE INHIBITORS

Pharmaceutical compositions comprising 2-[[2-[(3R)-3-Amino-piperidinyl)-5-fluoro-6-oxo-6H-pyrimidinyl]methyl]-benzonitrile and pharmaceutically acceptable salts thereof are provided as well as kits and articles of manufacture comprising the pharmaceutical

Dipeptidyl peptidase inhibitors

Compounds, pharmaceuticals, kits and methods are provided for use with DPP-IV inhibitors comprising Formula I: wherein the substituents are as described herein.