2802-61-1

Basic information

• Product Name: 2,4-DIFLUOROPYRIMIDINE
• Synonyms: 2,4-DIFLUOROPYRIMIDINE;Pyrimidine, 2,4-difluoro- (6CI,8CI,9CI);2,4-Difluoropyrimidine 98%;2,4-Difluoropyrimidine98%;NSC 331813;EOS-61621
• CAS NO: 2802-61-1
• Molecular Formula: C₄H₂F₂N₂
• Molecular Weight: 116.07
• EINECS: -0
• Product Categories: PYRIMIDINE;Halides;Pyrazines, Pyrimidines & Pyridazines;Heterocyclic Compounds;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 2802-61-1.mol

Chemical Properties

• Boiling Point: 118-120 °C
• Flash Point: 106 °F
• Appearance: /
• Density: 1.359 g/mL at 25 °C
• Vapor Pressure: 2200mmHg at 25°C
• Refractive Index: n20/D 1.432
• PKA: -2.52±0.20(Predicted)
• CAS DataBase Reference: 2,4-DIFLUOROPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIFLUOROPYRIMIDINE(2802-61-1)
• EPA Substance Registry System: 2,4-DIFLUOROPYRIMIDINE(2802-61-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 10-22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2802-61-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Difluoropyrimidine is used as a starting material for the synthesis of 3-Pyrimidin-4-yl-oxazolidin-2-one derivatives, which are mutant isocitrate dehydrogenase (IDH1) inhibitors. These inhibitors play a crucial role in the treatment of certain types of cancer by targeting the mutated IDH1 enzyme, which is often found in various malignancies.
Additionally, 2,4-Difluoropyrimidine is used as a starting material for the synthesis of N,N′-(1,4-phenylenebis(methylene))bis(2-fluoropyrimidin-4-amine), which are chemokine receptor type 4 (CXCR4) antagonists. These antagonists have potential applications in the treatment of various diseases, including cancer, by blocking the CXCR4 receptor and disrupting the chemotactic signaling pathways involved in tumor growth and metastasis.

Synthesis

Crown ethers are able to enhance the performance of KF in two ways. Firstly, they complex the potassium cation making a better fluoride source and secondly they increase the solubility of KF in the solvent. KF with a catalytic amount of dicyclohexano-18-crown-6 in tetraglyme converted 2,4-dichloropyrimidine into 2,4-difluoropyrimidine.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 22, p. 149, 1985 DOI: 10.1002/jhet.5570220137

InChI:InChI=1/C3ClF5/c4-2(6)1(5)3(7,8)9/b2-1+

Upstream product

• 3934-20-1 2,6-Dichloropyrimidine 

Downstream Products

• 96548-92-4 2-diisopropylamino-4-fluoropyrimidine 
• 96548-93-5 4-diisopropylamino-2-fluoropyrimidine 
• 898194-29-1 MSX-193 
• 1450596-71-0 N-(2,4-dimethoxybenzyl)-2-fluoropyrimidin-4-amine 
• 96548-91-3 4-amino-2-fluoropyrimidine 
• 1429181-06-5 (S)-3-(2-fluoropyrimidin-4-yl)-4-isopropyloxazolidin-2-one 
• 881207-34-7 5-Bromo-N-(2-fluoropyrimidin-4-yl)-N-methyl-2-phenylpyrimidin-4-amine 
• 881207-42-7 5-fluoro-N-(2-fluoropyrimidin-4-yl)-N-methyl-2-phenylpyrimidin-4-amine 

Relevant articles and documents

The proton sponge-triethylamine tris(hydrogen fluoride) system as a selective nucleophilic fluorinating reagent for chlorodiazines

The proton sponge-triethylamine tris(hydrogen fluoride) mixture provides a mild and efficient fluorinating - reagent for the selective introduction of a fluorine atom, by halogen exchange, into dichlorodiazines. (C) 2000 Elsevier Science Ltd.

Selective fluorination by halogen exchange of chlorodiazines and chloropyridines promoted by the 'proton sponge' - Triethylamine tris(hydrogen fluoride) system

The 'proton sponge' - triethylamine tris(hydrogen fluoride) mixtures provide a mild and efficient fluorinating reagent to introduce selectively fluorine atoms by halogen exchange into chlorodiazines and chloronitropyridine series.

Metalation of diazines. XI. Directed ortho-lithiation of fluoropyrimidines and application to synthesis of an azacarboline

For the first time fluoropyrimidines were successfully lithiated. The resulting lithio derivatives were reacted with various electrophiles for the synthesis of new pyrimidines. The synthesis of an azacarboline derivative is reported.

Fluorinated Heterocyclic Compounds. 2. 2,4-Difluoro and 4-Amino-2-fluoropyrimidines, Nucleoside Base Analogs

Nucleoside base analogs in which fluoro substituents replace the enolic hydroxy groups of uracil, thymine and cytosine have been prepared.Improved methods for the preparation and isolation of the known 2,4-difluoropyrimidine, 2,4-difluoro-6-methylpyrimidine and the new 2,4-difluoro-5-methylpyrimidine, 2-fluoro-4-aminopyrimidine, 4-fluoro-2-aminopyrimidine, and other alkylaminofluoropyrimidines are described.