5-Bromo-2-pyridinecarbonitrile
[CAS# 97483-77-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Cyanopyridine
• Name: 5-Bromo-2-pyridinecarbonitrile
• Synonyms: 5-Bromo-2-cyanopyridine
• Molecular Formula: C₆H₃BrN₂
• Molecular Weight: 183.01
• CAS Registry Number: 97483-77-7
• EC Number: 628-634-9
• SMILES: C1=CC(=NC=C1Br)C#N

Properties

• Melting point: 128-132 ºC
• Boiling point: 100-110 ºC 3 mmHg)

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Hazard Statements: H301-H315-H318-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311

Discovory and Applicatios

5-Bromo-2-pyridinecarbonitrile is an organic compound consisting of a bromine atom, a nitrile group (-C≡N), and a pyridine ring. Its structure imparts significant versatility in various synthetic pathways, particularly in the field of medicinal chemistry and material science. The presence of both bromine and nitrile groups makes this compound a valuable intermediate in the preparation of more complex molecules, allowing for further functionalization at both the bromine position and the nitrile group.

The discovery and synthesis of 5-bromo-2-pyridinecarbonitrile came as part of ongoing research efforts in heterocyclic chemistry, where scientists have been focused on modifying pyridine-based structures for diverse chemical applications. Pyridine derivatives are essential in many natural and synthetic products, and the addition of a bromine atom and a nitrile group to the pyridine ring allows for a wide range of chemical transformations.

In the pharmaceutical industry, 5-bromo-2-pyridinecarbonitrile is widely used as a key intermediate in drug development. Its bromine atom enables it to undergo nucleophilic substitution reactions, facilitating the introduction of various functional groups at the 5-position. The nitrile group, meanwhile, can be transformed into amines, carboxylic acids, or other functional groups, depending on the synthetic needs. This flexibility makes it an ideal building block in the synthesis of biologically active compounds, particularly in the development of anti-inflammatory, antiviral, and anticancer agents.

Beyond pharmaceuticals, 5-bromo-2-pyridinecarbonitrile is also valuable in the production of agrochemicals. Its structure can be incorporated into various formulations aimed at enhancing crop protection, pest control, and plant growth regulation. The stability of the pyridine ring combined with the reactivity of the nitrile and bromine groups makes this compound highly adaptable in these applications.

Additionally, 5-bromo-2-pyridinecarbonitrile is used in materials science, particularly in the design of advanced organic materials. Its role as a precursor for complex molecules allows for the creation of specialty polymers, dyes, and other materials that require precise structural control. Its ability to easily participate in cross-coupling reactions, such as the Suzuki or Heck reactions, further highlights its utility in constructing larger, more intricate molecular frameworks.

References

2024. Ir-Catalyzed Borylation of Heterocycles Through C-H Activation. Functionalisation of Heterocycles through Transition Metal Catalyzed C-H Activation.
DOI: 10.1007/7081_2024_72

2023. Synthesis of inventive biphenyl and azabiphenyl derivatives as potential insecticidal agents against the cotton leafworm, Spodoptera littoralis. BMC Chemistry, 17(1).
DOI: 10.1186/s13065-023-01050-w

2017. Small Molecules as Long-Wavelength Fluorophores: Push-Pull Substituted 4-Alkoxy-1,3-thiazoles. Synthesis, 49(22).
DOI: 10.1055/s-0036-1588581