Cas no 5750-74-3 (2,5-Dichloro-4-methoxypyrimidine)

2,5-Dichloro-4-methoxypyrimidine is a chlorinated pyrimidine derivative with a methoxy substituent at the 4-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the pharmaceutical and agrochemical industries. Its dichloro and methoxy functional groups enhance reactivity, making it suitable for nucleophilic substitution reactions and further derivatization. The electron-withdrawing chlorine atoms improve electrophilicity, while the methoxy group contributes to stability and solubility in organic solvents. This structural combination allows for selective modifications, facilitating the synthesis of complex heterocyclic compounds. It is commonly used in the preparation of active pharmaceutical ingredients (APIs) and specialty chemicals, offering a balance of reactivity and handling stability.
2,5-Dichloro-4-methoxypyrimidine structure
5750-74-3 structure
Product Name:2,5-Dichloro-4-methoxypyrimidine
CAS No:5750-74-3
MF:C5H4Cl2N2O
MW:179.004058837891
MDL:MFCD11858598
CID:1040791
PubChem ID:49761746
Update Time:2025-06-09

2,5-Dichloro-4-methoxypyrimidine Chemical and Physical Properties

Names and Identifiers

    • 2,5-Dichloro-4-methoxypyrimidine
    • C5H4Cl2N2O
    • 2,5-dichloro-4-methoxy-pyrimidine
    • 2.5-Dichlor-4-methoxy-pyrimidin
    • ACN-S001414
    • AK103404
    • ANW-64826
    • CTK8C0521
    • QC-85
    • FNXVYHFDDCNERP-UHFFFAOYSA-N
    • Pyrimidine,2,5-dichloro-4-methoxy-
    • 8473AB
    • Pyrimidine, 2,5-dichloro-4-methoxy-
    • 2,5-Dichloro-4-methoxypyrimidine, AldrichCPR
    • SCHEMBL1981633
    • SB57340
    • 5750-74-3
    • DTXSID90678474
    • SY020945
    • AKOS016005080
    • DA-19247
    • AS-61138
    • CS-0021206
    • EN300-7225126
    • MFCD11858598
    • MDL: MFCD11858598
    • Inchi: 1S/C5H4Cl2N2O/c1-10-4-3(6)2-8-5(7)9-4/h2H,1H3
    • InChI Key: FNXVYHFDDCNERP-UHFFFAOYSA-N
    • SMILES: ClC1=CN=C(N=C1OC)Cl

Computed Properties

  • Exact Mass: 354.02313
  • Monoisotopic Mass: 177.97
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 114
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 35
  • XLogP3: 2.1

Experimental Properties

  • Color/Form: NA
  • Density: 1.446±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 52-54 oC
  • Boiling Point: 303.7±22.0 °C at 760 mmHg
  • Flash Point: 194.8±23.2 °C
  • Refractive Index: 1.721
  • Solubility: Slightly soluble (5 g/l) (25 o C),
  • PSA: 55.13

2,5-Dichloro-4-methoxypyrimidine Pricemore >>

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Additional information on 2,5-Dichloro-4-methoxypyrimidine

2,5-Dichloro-4-methoxypyrimidine: A Comprehensive Overview

The compound 2,5-Dichloro-4-methoxypyrimidine, also known by its CAS number 5750-74-3, is a heterocyclic aromatic compound with significant applications in various fields. This compound belongs to the pyrimidine family, which is a six-membered ring consisting of four carbon atoms and two nitrogen atoms at positions 1 and 3. The substitution pattern of this compound includes two chlorine atoms at positions 2 and 5, and a methoxy group (-OCH3) at position 4. These substituents play a crucial role in determining the chemical properties and reactivity of the molecule.

Recent studies have highlighted the potential of 2,5-Dichloro-4-methoxypyrimidine in the field of medicinal chemistry. Researchers have explored its role as a building block for synthesizing bioactive compounds with potential therapeutic applications. For instance, derivatives of this compound have shown promising results in anti-cancer studies, particularly in targeting specific enzymes involved in cancer cell proliferation. The methoxy group at position 4 contributes to the compound's solubility and bioavailability, making it an attractive candidate for drug development.

In addition to its medicinal applications, 2,5-Dichloro-4-methoxypyrimidine has also found utility in agrochemicals. Its ability to inhibit certain enzymes related to plant growth regulation has led to its investigation as a potential herbicide or fungicide. Recent advancements in green chemistry have further enhanced the synthesis methods of this compound, making it more environmentally friendly and cost-effective.

The synthesis of 2,5-Dichloro-4-methoxypyrimidine typically involves multi-step reactions, often starting from readily available starting materials such as pyrimidine derivatives or chlorinated intermediates. Modern synthetic strategies have focused on improving yield and purity through optimized reaction conditions and catalysts. For example, microwave-assisted synthesis has been employed to accelerate reaction rates and reduce reaction times.

From a structural perspective, the presence of electron-withdrawing groups like chlorine atoms at positions 2 and 5 significantly influences the electronic properties of the pyrimidine ring. This makes the compound highly reactive towards nucleophilic substitution and electrophilic aromatic substitution reactions. The methoxy group at position 4 introduces electron-donating effects through resonance, which can modulate the reactivity of the molecule depending on the reaction conditions.

Recent research has also delved into the photochemical properties of 2,5-Dichloro-4-methoxypyrimidine. Studies have shown that this compound exhibits fluorescence under UV light due to its conjugated system. This property has opened up new avenues for its application in sensors and optoelectronic devices. Furthermore, its stability under various environmental conditions makes it suitable for long-term applications.

In conclusion, 2,5-Dichloro-4-methoxypyrimidine, with its unique structural features and versatile reactivity, continues to be a focal point in both academic and industrial research. Its potential applications span across medicine, agriculture, and materials science, making it a valuable compound for future innovations.

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