Cas no 181363-10-0 ((2-chloropyrimidin-4-yl)methanamine)

(2-Chloropyrimidin-4-yl)methanamine is a versatile pyrimidine derivative featuring a reactive 2-chloro substituent and an amino-functionalized methyl group at the 4-position. This bifunctional compound serves as a valuable intermediate in pharmaceutical and agrochemical synthesis, enabling selective nucleophilic substitution at the chlorinated position or further derivatization via the primary amine. The electron-deficient pyrimidine core enhances reactivity in cross-coupling reactions, while the aminomethyl group provides a convenient handle for conjugation or scaffold elaboration. Its crystalline solid form ensures good stability and handling characteristics. The compound's balanced lipophilicity (predicted LogP ~0.9) and molecular weight (143.57 g/mol) make it particularly useful in medicinal chemistry for developing kinase inhibitors and other biologically active heterocycles. Structural characterization typically includes 1H NMR (DMSO-d6) showing characteristic pyrimidine proton at δ 8.5 ppm and aminomethyl protons at δ 4.0 ppm.
(2-chloropyrimidin-4-yl)methanamine structure
181363-10-0 structure
Product Name:(2-chloropyrimidin-4-yl)methanamine
CAS No:181363-10-0
MF:C5H6ClN3
MW:143.574239253998
MDL:MFCD25977382
CID:113652
PubChem ID:45080138
Update Time:2025-07-02

(2-chloropyrimidin-4-yl)methanamine Chemical and Physical Properties

Names and Identifiers

    • 4-Pyrimidinemethanamine,2-chloro-
    • (2-chloropyrimidin-4-yl)methanamine
    • 4-Pyrimidinemethanamine, 2-chloro- hcl
    • C-(2-Chloro-pyrimidin-4-yl)-methylamine
    • 4-Pyrimidinemethanamine, 2-chloro- (9CI)
    • EN300-206918
    • FT-0724618
    • SCHEMBL445949
    • amino-methyl pyrimidine chloride
    • CS-0057788
    • AKOS006303396
    • AB58851
    • BB 0262366
    • 4-PYRIMIDINEMETHANAMINE, 2-CHLORO-
    • 181363-10-0
    • DA-09039
    • MDL: MFCD25977382
    • Inchi: 1S/C5H6ClN3/c6-5-8-2-1-4(3-7)9-5/h1-2H,3,7H2
    • InChI Key: YLWQRUVKEZYEED-UHFFFAOYSA-N
    • SMILES: ClC1=NC=CC(CN)=N1

Computed Properties

  • Exact Mass: 143.02518
  • Monoisotopic Mass: 143.025
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 1
  • Complexity: 88.3
  • 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: 51.8A^2
  • XLogP3: 0.1

Experimental Properties

  • PSA: 51.8

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Additional information on (2-chloropyrimidin-4-yl)methanamine

Comprehensive Overview of (2-chloropyrimidin-4-yl)methanamine (CAS No. 181363-10-0): Properties, Applications, and Industry Insights

(2-chloropyrimidin-4-yl)methanamine, identified by its CAS number 181363-10-0, is a specialized heterocyclic amine derivative with a pyrimidine backbone. This compound has garnered significant attention in pharmaceutical and agrochemical research due to its versatile molecular scaffold, which enables diverse functionalization. The presence of both a chloro substituent and an aminomethyl group at the 2- and 4-positions of the pyrimidine ring, respectively, makes it a valuable intermediate for synthesizing small-molecule inhibitors and bioactive compounds.

Recent trends in drug discovery highlight the growing demand for pyrimidine-based building blocks, with 181363-10-0 frequently appearing in patent literature. Researchers are particularly interested in its role in developing kinase inhibitors, a hot topic in oncology and autoimmune disease therapeutics. The compound’s structural flexibility allows for modifications that enhance target selectivity—a critical factor addressed in AI-driven molecular design platforms. Notably, computational studies suggest its potential in fragment-based drug discovery (FBDD), aligning with the industry’s shift toward high-efficiency lead optimization.

From a synthetic chemistry perspective, (2-chloropyrimidin-4-yl)methanamine serves as a precursor for cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig animations, which dominate discussions in green chemistry forums. Its chloropyrimidine moiety is reactive toward nucleophilic substitution, enabling the introduction of tailored functional groups—a feature leveraged in combinatorial chemistry workflows. Environmental considerations have also spurred interest in catalytic methods for its production, reducing reliance on hazardous reagents.

Analytical characterization of CAS 181363-10-0 typically involves HPLC purity testing and mass spectrometry, with structural confirmation via NMR spectroscopy. These techniques are frequently searched in conjunction with QC protocols for intermediates, reflecting the compound’s industrial relevance. Stability studies under varying pH conditions and thermal stress are also critical, as they inform formulation strategies for downstream applications.

In material science, derivatives of (2-chloropyrimidin-4-yl)methanamine have been explored for organic electronic materials, particularly in OLED and photovoltaic research. The pyrimidine core’s electron-deficient nature facilitates charge transport tuning, a key focus area for next-gen semiconductors. This interdisciplinary appeal underscores the compound’s value beyond traditional chemistry sectors.

Regulatory compliance for 181363-10-0 adheres to REACH and GMP guidelines, with suppliers emphasizing documentation transparency—a priority for contract manufacturing organizations (CMOs). Searches for scalable synthesis routes and cost-effective sourcing dominate B2B inquiries, reflecting market dynamics. Additionally, structure-activity relationship (SAR) studies leveraging this compound are frequently cited in open-access journals, aligning with the open science movement.

Future prospects for (2-chloropyrimidin-4-yl)methanamine include its integration into automated synthesis platforms and machine-learning-aided molecular libraries. As precision medicine advances, the demand for customized heterocycles like this will likely surge, solidifying its position as a high-value chemical entity in both academic and industrial settings.

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