Production Method 1

21190-87-4

83004-10-8

Reaction Conditions

1.1 Reagents: Triethylamine ,  Ethyl chloroformate Solvents: Tetrahydrofuran ;  0 °C
1.2 Reagents: Sodium borohydride Solvents: Water
2.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  0 °C → rt

Reference

Novel bisphosphonate inhibitors of the human farnesyl pyrophosphate synthase

De Schutter, Joris W.; et al, Bioorganic & Medicinal Chemistry Letters, 2010, 20(19), 5781-5786

Production Method 2

34160-40-2

83004-10-8

Reaction Conditions

1.1 Reagents: Calcium chloride ,  Sodium borohydride Solvents: Ethanol ;  3 h, 0 °C
2.1 Reagents: Carbon tetrabromide ,  Potassium carbonate ,  Triphenylphosphine Solvents: Dichloromethane ;  0 °C; overnight, 0 °C → rt

Reference

Library Synthesis, Screening, and Discovery of Modified Zinc(II)-Bis(dipicolylamine) Probe for Enhanced Molecular Imaging of Cell Death

Plaunt, Adam J.; et al, Bioconjugate Chemistry, 2014, 25(4), 724-737

Production Method 3

626-05-1

83004-10-8

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  < -70 °C; 15 min, < -70 °C
1.2 Solvents: Dimethylformamide ;  30 s, < -70 °C; 15 min, -78 °C
1.3 Reagents: Acetic acid ,  Sodium borohydride ;  -78 °C → rt
1.4 Reagents: Ammonium chloride Solvents: Water ;  rt
2.1 Reagents: Hydrogen bromide Solvents: Water ;  12 h, reflux
2.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized

Reference

Iron complexes of new hydrophobic derivatives of tris(2-pyridylmethyl)amine: synthesis, characterization, and catalysis of alkane oxygenation by H2O2

Guisado-Barrios, Gregorio; et al, Journal of Coordination Chemistry, 2010, 63(14-16), 2642-2658

Production Method 4

33674-96-3

83004-10-8

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  0 °C → rt

Reference

Novel bisphosphonate inhibitors of the human farnesyl pyrophosphate synthase

De Schutter, Joris W.; et al, Bioorganic & Medicinal Chemistry Letters, 2010, 20(19), 5781-5786

Production Method 5

33674-96-3

83004-10-8

Reaction Conditions

1.1 Reagents: Hydrogen bromide Solvents: Water ;  4 h, rt → 120 °C; cooled
1.2 Reagents: Sodium bicarbonate ;  pH 5 - 6

Reference

Solid State and Solution Characterization of Chiral, Conformationally Mobile Tripodal Ligands

Canary, James W.; et al, Inorganic Chemistry, 1998, 37(24), 6255-6262

Production Method 6

5315-25-3

83004-10-8

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Dichloromethane ,  Water ;  5 - 6 h, rt

Reference

Ruthenium complexes bearing N-heterocyclic carbene based CNC and CNC?H2C' pincer ligands: Photophysics, electrochemistry, and solar energy conversion

Jain, Nimisha; et al, Journal of Organometallic Chemistry, 2022, 959,

Production Method 7

5315-25-3

83004-10-8

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Benzene ;  24 h, 90 °C

Reference

Optimization of 2-aminothiazole derivatives as CCR4 antagonists

Wang, Xuemei; et al, Bioorganic & Medicinal Chemistry Letters, 2006, 16(10), 2800-2803

Production Method 8

1824-81-3

83004-10-8

Reaction Conditions

Reference

A new ligand containing a pyridine, a 2,2'-bipyridine and a carboxylate moiety and its lanthanide polymeric complexes: Synthesis, characterization and photophysical studies

Bejan, Claudia C. C.; et al, Inorganic Chemistry Communications, 2006, 9(5), 464-468

Production Method 9

1824-81-3

83004-10-8

Reaction Conditions

1.1 Reagents: Bromine ,  Hydrogen bromide Solvents: Water ;  -20 °C
1.2 Reagents: Sodium nitrite ;  0 °C
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Dichloromethane ,  Water ;  reflux

Reference

Catalytic etherification of N-protected tris(hydroxymethyl)aminomethane for the synthesis of ligands with C3 symmetry

Weibel, Nicolas; et al, Tetrahedron Letters, 2006, 47(11), 1793-1796

Production Method 10

5315-25-3

83004-10-8

82315-66-0

Reaction Conditions

1.1 Reagents: Bromine Solvents: Benzene ,  Water
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Alternative approach to the free radical bromination of oligopyridine benzylic-methyl group

Bedel, Sebastien; et al, Tetrahedron Letters, 2002, 43(9), 1697-1700

2-Bromo-6-(bromomethyl)pyridine Raw materials

• 2,6-Dibromopyridine
• 6-Bromo-2-pyridinecarboxaldehyde
• 6-bromopyridine-2-carboxylic acid
• 2-Bromo-6-methylpyridine
• (6-Bromopyridin-2-yl)methanol
• 6-methylpyridin-2-amine

2-Bromo-6-(bromomethyl)pyridine Preparation Products

• 2-Bromo-6-(bromomethyl)pyridine (83004-10-8)
• 2-Bromo-6-(dibromomethyl)pyridine (82315-66-0)

• 1. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
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2-Bromo-6-(bromomethyl)pyridine (CAS No. 83004-10-8): A Comprehensive Overview

2-Bromo-6-(bromomethyl)pyridine (CAS No. 83004-10-8) is a brominated pyridine derivative that has garnered significant attention in the fields of organic synthesis, materials science, and pharmacology. This compound, characterized by its bromine substituents at positions 2 and 6 of the pyridine ring, exhibits unique chemical properties that make it a valuable building block in various research and industrial applications. Recent studies have highlighted its potential in the development of advanced materials, drug delivery systems, and as a precursor for bioactive molecules.

The chemical structure of 2-Bromo-6-(bromomethyl)pyridine consists of a pyridine ring with bromine atoms at positions 2 and 6. The bromomethyl group (-CH?Br) at position 6 introduces additional reactivity, enabling this compound to participate in a wide range of organic reactions. Its physical properties, including a melting point of approximately 155°C and a boiling point around 355°C, make it suitable for use in high-temperature synthetic processes. The compound is also sparingly soluble in water but dissolves readily in organic solvents such as dichloromethane and THF.

Recent advancements in synthetic chemistry have led to innovative methods for the preparation of 2-Bromo-6-(bromomethyl)pyridine. One notable approach involves the bromination of pyridine derivatives using N-bromosuccinimide (NBS) under radical conditions. This method not only ensures high yields but also allows for precise control over the substitution pattern on the pyridine ring. Another emerging technique employs transition-metal-catalyzed cross-coupling reactions, which enable the construction of complex pyridine-based architectures incorporating brominated substituents.

The chemical reactivity of 2-Bromo-6-(bromomethyl)pyridine is primarily influenced by the electron-withdrawing nature of the bromine atoms and the presence of the reactive bromomethyl group. These features make it an excellent substrate for nucleophilic aromatic substitution (SNAr), elimination reactions, and coupling reactions. For instance, recent studies have demonstrated its utility in Suzuki-Miyaura cross-couplings, where it serves as a versatile electrophile for constructing biaryl compounds with unprecedented efficiency.

In terms of applications, 2-Bromo-6-(bromomethyl)pyridine has found significant use in the synthesis of heterocyclic compounds, which are widely employed in pharmaceuticals and agrochemicals. Its ability to act as a precursor for bioactive molecules has been exploited in drug discovery programs targeting various diseases, including cancer and infectious diseases. Moreover, this compound has been incorporated into polymer frameworks to create advanced materials with tailored electronic and mechanical properties.

Recent research has also explored the potential of 2-Bromo-6-(bromomethyl)pyridine in energy storage applications. For example, studies have shown that its derivatives can serve as cathode materials in lithium-ion batteries due to their high redox activity and stability under cycling conditions. Additionally, its role as a building block for metal-organic frameworks (MOFs) has opened new avenues for gas storage and catalysis.

The toxicological profile of 2-Bromo-6-(bromomethyl)pyridine is an area of ongoing investigation. While preliminary data suggest that it exhibits moderate cytotoxicity against certain cancer cell lines, further studies are required to fully understand its safety profile and potential risks associated with occupational exposure.

In conclusion, 2-Bromo-6-(bromomethyl)pyridine (CAS No. 83004-10-8) is a versatile compound with a rich array of chemical properties that make it an invaluable tool in modern chemistry. Its applications span across multiple disciplines, from organic synthesis to materials science, and recent advancements have underscored its potential for future innovations in drug development and energy storage technologies.

• 656258-97-8(2,2'-Bipyridine, 6-bromo-6'-(bromomethyl)-)
• 1227563-56-5(3,6-Dibromo-2-(bromomethyl)pyridine)
• 5315-25-3(2-Bromo-6-methylpyridine)
• 113385-63-0(3-bromo-1-(dibromomethyl)isoquinoline)
• 937268-66-1(2-Bromo-6-(1-bromoethyl)pyridine)
• 1804381-30-3(2-Bromo-6-bromomethyl-4-fluoropyridine)
• 32938-46-8(2-bromo-6-(bromomethyl)pyridine hydrobromide)
• 478620-05-2(PYRIDINE, 2-BROMO-6-METHYL-, HYDROCHLORIDE)
• 1805123-59-4(4-Amino-2-bromo-6-(bromomethyl)pyridine)
• 82315-66-0(2-Bromo-6-(dibromomethyl)pyridine)