1093418-77-9

Basic information

• Product Name: 2,5-Diiodopyrazine
• Synonyms: 2,5-Diiodopyrazine
• CAS NO: 1093418-77-9
• Molecular Formula: C₄H₂I₂N₂
• Molecular Weight: 331.88102
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1093418-77-9.mol

Chemical Properties

• Melting Point: 141 °C
• Boiling Point: 329.733 °C at 760 mmHg
• Flash Point: 153.217 °C
• Appearance: /
• Density: 2.765 g/cm³
• PKA: -3.70±0.10(Predicted)
• CAS DataBase Reference: 2,5-Diiodopyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diiodopyrazine(1093418-77-9)
• EPA Substance Registry System: 2,5-Diiodopyrazine(1093418-77-9)

Safety Data

• Hazardous Substances Data: 1093418-77-9(Hazardous Substances Data)

Upstream product

• 290-37-9 1,4-pyrazine 
• 23229-26-7 2-5-dibromopyrazine 

Downstream Products

• 1361113-83-8 2,5-Bis((4,5-bis(dodecyloxy)-2-(pyridin-2-ylethynyl)phenyl)-ethynyl)pyrazine 
• 1361113-87-2 2,5-bis((4,5-bis(dodecyloxy)-2-(pyridin-3-ylethynyl)phenyl)-ethynyl)pyrazine 
• 1361113-94-1 2,5-bis((4,5-bis(dodecyloxy)-2-(pyridin-4-ylethynyl)phenyl)-ethynyl)pyrazine 

Relevant articles and documents

New lithium-zincate approaches for the selective functionalisation of pyrazine: Direct dideprotozincation vs. nucleophilic alkylation

Comparing the reactivity of the related lithium zincates [(THF)LiZn(TMP)tBu2] (1) and [(PMDETA)LiZn tBu3] (2) towards pyrazine discloses two new bimetallic approaches for the selective 2,5-dideprotonation and room temperature C-H alkylation of this sensitive heterocycle.

Synthesis of 2,5-diiodopyrazine by deprotonative dimetalation of pyrazine

The deproto-metalation reactions of pyrimidine and pyrazine were regioselectively carried out using lithium tris(2,2,6,6-tetramethylpiperidino) cadmate in tetrahydrofuran at room temperature. This result was demonstrated by subsequent trapping with iodine to afford 4-iodopyrimidine and 2-iodopyrazine in 71% and 63% yields, respectively. The same reaction performed on pyridazine afforded a mixture of the 3- and 4-iodo derivatives (55% and 41% yields, respectively). From pyrazine, access to the 2,5-diiodo derivative (40% on a 25 mmol scale) proved possible using a larger amount of base (1 equiv instead of 0.33). Georg Thieme Verlag Stuttgart.

Evidence of enhanced conjugation in ortho -arylene ethynylenes with transition metal coordination

The effective conjugation of ortho and ortho-alt-para-arylene ethynylenes, with appropriately positioned pyridine and pyrazine heterocycles, increases upon binding to Ag(I) and Pd(II) cations. Significant bathochromic shifts in the electronic spectra, wit

Alkali-metal mediated zincation of N-heterocyclic substrates using the lithium zincate complex, (THF)Li(TMP)Zn(tBu)2 and applications in in situ cross coupling reactions

This study investigates the ability of the mixed-metal reagent [Li(TMP)Zn(tBu)2] 1 to promote direct Zn-H exchange reactions (zincations) of a wide range of N-heterocyclic molecules. The generated metallated intermediates from these reactions are intercepted with I2 and some of them are also employed as precursors in Pd-catalysed Negishi cross-coupling applications. A comparison with recent precedents in metallation chemistry reveals that for some of these heterocycles, 1 allows improved conversions, under milder conditions and in certain cases, even gives unique regioselectivities.

Deprotonative cadmation of functionalized aromatics

This communication describes the deproto-metalation of a large range of aromatics including heterocycles using a newly developed lithium-cadmium base; the reaction proceeds at room temperature with an excellent chemoselectivity and efficiency, and proved to be regioselective in most cases. The Royal Society of Chemistry.