2-Amino-3-bromo-5-fluoropyridine (869557-43-7)

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2-amino-5-fluoropyridinium,tetrachlorocuprate was synthesized and characterized structurally and magnetically. While the data may be modeled as a strong-rung ladder, computation studies show the compound to be 3D-antiferromagnetic with a singlet ground state.

Reaction of CuCl2 with 2-amino-5-fluoropyridine and HCl in aqueous solution yields bis(2-amino-5-fluoropyridinium) tetrachlorocuprate(II), (5FAP)2CuCl4, (1). The complex crystallizes in the monoclinic space group P21/c with cell dimensions a = 6.926(7) Å, b = 21.73(2) Å, c = 10.911(10) Å, β = 100.19(2)°, V = 1616(3) Å3, and R1 = 0.0424 based on 2640 independent reflections. The crystal packing shows that each tetrachlorocuprate ion has four nearest-neighbor Cu(II) ions through three types of Cu−Cl···Cl−Cu potential magnetic interactions:  one short Cl···Cl distance (d1 = 3.657 Å) and two longer Cl···Cl distances (d2 = 4.073 Å) that form a layered distorted honeycomb structure. The third nearest neighbor (d3 = 4.239 Å) links these layers into a three-dimensional structure. Both powder and single-crystal magnetic susceptibility measurements on 1, over the temperature range of 1.8−325 K, show significant antiferromagnetic interactions. Attempts to analyze the data using a variety of models showed a best fit to the strong-rung ladder model, with 2Jrung = −17.170(14) and 2Jrail = −5.94(5) K [−11.92(1) and −4.13(3) cm-1, respectively] for the powder, although a comparable result is obtained using an alternate chain model. However, neither of these two models is compatible with a layered distorted honeycomb crystal packing structure. A first-principles bottom-up theoretical study using the 165 K crystallographic data reproduces the macroscopic properties and reveals that at low temperature the crystal has a 3D magnetic topology (all three magnetic pathways are significant) and a singlet ground state.

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2-Amino-3-bromo-5-fluoropyridine (869557-43-7) Specifications

CAS 869557-43-7
CAS Min % 95%
CAS Max % 100%
MDL Number MFCD03092924
Chemical Name or Material 2-Amino-3-bromo-5-fluoropyridine
Infrared Spectrum Authentic
Physical Form powder
Packaging Glass bottle
Molecular Formula C5H4BrFN2
Molecular Weight (g/mol) 191.00
Color white
Melting Point 61-63°C
Assay 97%


2-Amino-3-bromo-5-fluoropyridine (869557-43-7) Safety and HandlingAPICMO hazard icons

 (869557-43-7) GHS H Statement

  • Harmful if swallowed
  • Causes skin irritation.
  • Causes serious eye damage
  • May cause respiratory irritation.

2-Amino-3-bromo-5-fluoropyridine GHS P Statement

  • Avoid breathing dust/fume/gas/mist/vapors/spray.
  • Wear protective gloves/protective clothing/eye protection/face protection.
  • IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
  • In case of skin contact: Wash off with soap and plenty of water. Consult a physician.
  • If swallowed: Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician
  • Store locked up.

WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.

2-Amino-3-bromo-5-fluoropyridine (869557-43-7) Articles

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A series of 2,3,4,4a,10,10a-hexahydropyrano[3,2-b]chromene analogs was developed that demonstrated high selectivity (>2000-fold) for BACE1 vs Cathepsin D (CatD). Three different Asp-binding moieties were examined: spirocyclic acyl guanidines, aminooxazolines, and aminothiazolines in order to modulate potency, selectivity, efflux, and permeability.

Journal of Medicinal Chemistry 2014 vol. 57 # 23 p. 10112 – 10129

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