5-Bromo-N,N-diethylpicolinamide: Properties & Lab FAQ

5-Bromo-N,N-diethylpicolinamide is a brominated pyridine-2-carboxamide building block widely used in medicinal chemistry and organic synthesis as a versatile halogenated heterocyclic intermediate.

Chemical Name

5-Bromo-N,N-diethylpicolinamide

SKU / Catalog Number

B730902

Compound Class

Brominated pyridinecarboxamide (halogenated heterocycle)

Core Structure

Pyridine-2-carbonyl scaffold with bromine at position 5 and N,N-diethyl amide

Primary Research Use

Synthetic intermediate for cross-coupling reactions and medicinal chemistry programs

Supplier

Aladdin Scientific

What Is 5-Bromo-N,N-diethylpicolinamide?

5-Bromo-N,N-diethylpicolinamide is a halogenated heteroaromatic amide comprising a pyridine ring bearing a bromine substituent at the 5-position and an N,N-diethylcarboxamide group at the 2-position. This combination of a directing amide moiety and a reactive aryl bromide makes the compound a highly flexible synthetic building block.

The picolinamide (pyridine-2-carboxamide) scaffold is well established in coordination chemistry and organic synthesis. The N,N-diethyl substitution on the amide nitrogen modulates both the electronic character of the carbonyl and the steric environment, influencing reactivity in downstream transformations. The aryl bromide at C-5 serves as a handle for palladium-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and related methodologies.

Key Chemical Properties and Handling

As a brominated aromatic amide, 5-Bromo-N,N-diethylpicolinamide is expected to be a solid or low-melting crystalline material at room temperature, consistent with compounds of comparable molecular weight and structure in its class. Specific melting point, exact molecular weight, and spectroscopic data should be confirmed from the certificate of analysis (CoA) supplied with each lot.

Standard laboratory precautions should be observed: use of appropriate personal protective equipment (gloves, lab coat, eye protection), work in a well-ventilated area or fume hood, and avoidance of inhalation or skin contact. Organobromine compounds should be handled with care; consult the Safety Data Sheet (SDS) for full hazard classification, first-aid measures, and disposal guidance.

For storage, the compound should generally be kept in a tightly sealed container, away from light and moisture, at cool temperatures (typically 2–8 °C or as indicated on the product label). Confirm storage conditions on the product page or CoA before use.

Common Research and Synthetic Applications

The primary utility of 5-Bromo-N,N-diethylpicolinamide in synthetic chemistry lies in its dual functionality: the aryl C–Br bond and the pyridyl amide directing group. These features enable a range of applications:

• Palladium-catalyzed cross-coupling: The aryl bromide undergoes Suzuki–Miyaura coupling with boronic acids/esters, Negishi coupling with organozincs, and related transformations to install diverse aryl, heteroaryl, or alkenyl substituents at C-5.
• Directed C–H functionalization: The picolinamide moiety is a well-known bidentate directing group that can facilitate transition-metal-catalyzed C–H activation on tethered substrates.
• Medicinal chemistry fragment libraries: Bromopyridinecarboxamides are valued fragments in drug discovery due to the pharmacophoric importance of the pyridine nitrogen and the amide bond.
• Ligand and coordination chemistry: The pyridyl-amide scaffold can coordinate to metal centers, making derivatives useful in catalyst development.

Ordering, Specifications, and Quality

5-Bromo-N,N-diethylpicolinamide is available from Aladdin Scientific under catalog number B730902. Researchers and procurement teams can place orders directly through the Aladdin Scientific website or by contacting the sales team.

Each lot is accompanied by a Certificate of Analysis (CoA) detailing purity (typically assessed by HPLC or NMR), lot number, and storage recommendations. Researchers requiring specific purity grades or larger custom quantities are encouraged to contact Aladdin Scientific customer service for tailored quotations.

For the most current pricing, available pack sizes, and stock status, please refer to the product listing on the Aladdin Scientific website or contact your regional representative.

Frequently asked questions

What is the catalog number for 5-Bromo-N,N-diethylpicolinamide at Aladdin Scientific?

The catalog number (SKU) for 5-Bromo-N,N-diethylpicolinamide at Aladdin Scientific is B730902. You can search this SKU directly on the Aladdin Scientific website to access the product page, pricing, and CoA downloads.

What types of chemical reactions is 5-Bromo-N,N-diethylpicolinamide commonly used for?

This compound is primarily used as a building block in palladium-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Negishi) via its aryl C–Br bond. The picolinamide moiety additionally serves as a bidentate directing group in transition-metal-catalyzed C–H functionalization, and the scaffold is valuable in medicinal chemistry fragment-based drug discovery programs.

How should 5-Bromo-N,N-diethylpicolinamide be stored to maintain stability?

As a general guideline for compounds of this class, the reagent should be stored in a tightly sealed container at cool temperatures (2–8 °C is typical), protected from light and moisture. Always verify the specific storage conditions printed on the product label or CoA for each lot, as manufacturer recommendations take precedence.

Can I obtain a Certificate of Analysis (CoA) for this product?

Yes. Aladdin Scientific provides a Certificate of Analysis for each lot of B730902. The CoA includes purity data, lot number, and storage instructions. You can download the CoA from the product page on the Aladdin Scientific website using your lot number, or request it from customer service.

Is 5-Bromo-N,N-diethylpicolinamide suitable for medicinal chemistry applications?

Yes. Bromopyridinecarboxamide scaffolds are widely valued in medicinal chemistry and fragment-based drug discovery due to the pharmacophoric significance of the pyridine nitrogen, the hydrogen-bond-accepting carbonyl, and the readily modifiable aryl bromide. This compound can serve as a starting material or intermediate for generating diverse analogue libraries.

References

1. Aladdin Scientific product page: 5-Bromo-N,N-diethylpicolinamide, SKU B730902.
2. General reference on picolinamide directing groups in C–H functionalization: textbook-level knowledge; specific primary literature not cited in source material.
3. General reference on Suzuki–Miyaura and related palladium-catalyzed cross-coupling reactions: textbook-level knowledge; no specific citation provided in source material.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.