89667-09-4

Basic information

• Product Name: 3-Pyridinemethanol, a-(2-bromophenyl)-
• Synonyms: (2-bromophenyl)(3-pyridyl)methanol;(2-bromophenyl)pyridin-3-ylmethanol;(2-Bromo-phenyl)-pyridin-3-yl-methanol
• CAS NO: 89667-09-4
• Molecular Formula: C12H10BrNO
• Molecular Weight: 264.121
• Mol File: 89667-09-4.mol

Chemical Properties

• CAS DataBase Reference: 3-Pyridinemethanol, a-(2-bromophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinemethanol, a-(2-bromophenyl)-(89667-09-4)
• EPA Substance Registry System: 3-Pyridinemethanol, a-(2-bromophenyl)-(89667-09-4)

Safety Data

• Hazardous Substances Data: 89667-09-4(Hazardous Substances Data)

Upstream product

• 626-55-1 3-Bromopyridine 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 5424-19-1 3-Benzoylpyridine 
• 795309-03-4 2-bromobenzyl-3-pyridine 
• 795309-00-1 acetic acid (2-bromophenyl)pyridin-3-ylmethyl ester 
• 77744-06-0 (2-bromophenyl)(3-pyridyl)methanone 
• 6270-47-9 1-phenyl-1-(pyrid-3-yl)methanol 

Relevant articles and documents

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Intramolecular 6-exolendo-trig and 5-exo-trig cyclisations of aryl radical intermediates to the α-, β- P- and γ-carbons of pyridine have been shown to be facile processes at neutral pH. The tether conjoining the radical donor to the pyridine plays an important role in determining the outcome of the reaction. When a Z-alkene is used as a tether, ortho-cyclisation proceeds in good yield. A more complex course is followed when a saturated two carbon tether is employed, leading to products derived from hydrogen atom abstraction, ipso-cyclisation and ortho-cyclisation pathways. All attempts to effect 5-exolendo-trig cyclisations failed. Tributyltin hydride, tris(trimethylsilyl)silane, tris(trimethylsilyl)germane and, in part, samarium(II) iodide can each be employed as mediators of the reaction.

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Compositions and methods using silicon-based cross-coupling agents in the formation of carbon-carbon and carbon-nitrogen bonds are described.

Orientation and alkylation effects on cation-π interactions in aqueous solution

We have investigated the orientation dependence of the cation-π interaction between a phenyl ring and a pyridinium ring in the context of a flexible model system in water. Of the four possible positions of the pyridinium nitrogen, ipso, ortho, meta, and para, we found a variation in the interaction energy of about 0.75 kcal mol-1, with the stacking of the ipso-pyridinium ring providing the strongest interaction. The observed stability is attributed to the maximization of the electrostatic interaction, minimization of rotamers, and possible differences in hydration phenomena arising from alkylation.

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