2-Bromo-5-nitrothiazole: Properties, Handling & Lab Use Guide

2-Bromo-5-nitrothiazole is a halogenated nitroheterocyclic building block widely employed in medicinal chemistry and synthetic organic chemistry for the preparation of pharmacologically active thiazole derivatives.

Chemical Name

2-Bromo-5-nitrothiazole

Molecular Formula

C₃HBrN₂O₂S

Molecular Weight

209.02 g/mol

CAS Number

3034-48-8

Appearance

Pale yellow to yellow crystalline solid

Key Functional Groups

C–Br bond at position 2; nitro group (–NO₂) at position 5 of the thiazole ring

Primary Application

Electrophilic and nucleophilic substitution reactions; cross-coupling chemistry; pharmaceutical intermediate synthesis

Storage Condition

Store in a cool, dry, well-ventilated area away from light and moisture; keep container tightly closed

Chemical Properties and Structure

2-Bromo-5-nitrothiazole (CAS 3034-48-8, molecular formula C₃HBrN₂O₂S, MW 209.02 g/mol) is a five-membered heterocyclic compound containing both sulfur and nitrogen atoms in the thiazole ring. The bromine substituent at C-2 and the electron-withdrawing nitro group at C-5 create a highly electron-deficient ring system. This electronic configuration makes the compound exceptionally reactive toward nucleophilic aromatic substitution (S_NAr) at C-2, where the bromine acts as a leaving group activated by the combined electron-withdrawing effects of the adjacent nitrogen and the nitro group at C-5.

The compound also serves as an excellent electrophilic partner in palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings, enabling efficient C–C and C–heteroatom bond formation. The nitro group can itself be further transformed by reduction to an amine, providing additional synthetic versatility.

Synthetic Applications and Use Cases

2-Bromo-5-nitrothiazole is a versatile heterocyclic building block used extensively in medicinal chemistry for the synthesis of bioactive molecules. Key synthetic applications include:

• Nucleophilic Aromatic Substitution: The C-2 bromine is readily displaced by amines, thiols, alkoxides, and other nucleophiles under mild conditions, affording 2-substituted-5-nitrothiazole derivatives relevant to drug discovery programs.
• Palladium-Catalyzed Cross-Coupling: Under standard cross-coupling conditions (e.g., Pd(PPh₃)₄ or Pd(dppf)Cl₂, base, solvent), the C–Br bond participates in Suzuki, Sonogashira, and Negishi couplings to introduce aryl, alkynyl, or alkyl groups at C-2.
• Reduction of the Nitro Group: The C-5 nitro group can be selectively reduced to an amine (e.g., using Fe/AcOH, Zn/NH₄Cl, or catalytic hydrogenation), giving access to 2-bromo-5-aminothiazole or fully functionalized 2,5-disubstituted thiazole pharmacophores.
• Pharmaceutical Intermediate: Thiazole-containing scaffolds incorporating nitro or amino groups at C-5 appear in a broad range of pharmacological agents, including antimicrobial, antiparasitic, and kinase-inhibitor lead compounds.

Researchers should optimize reaction conditions (temperature, solvent, base, catalyst loading) empirically, as the strong electron-withdrawing character of the nitro group can influence reaction rates and selectivity.

Safe Handling and Storage Guidelines

Safe and responsible handling of 2-Bromo-5-nitrothiazole requires adherence to standard laboratory safety practices for halogenated nitro-heterocycles. Researchers and lab managers should observe the following precautions:

• Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves (e.g., nitrile), safety goggles, and a laboratory coat. Work in a well-ventilated fume hood to minimise inhalation of dust or vapours.
• Storage: Store the compound in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified on the Certificate of Analysis), dry, and well-ventilated location away from direct light, heat sources, oxidising agents, and strong bases or acids.
• Stability: As with most aromatic nitro compounds, avoid exposure to reducing agents, heat, and shock or friction in bulk quantities. Keep away from flammable materials.
• Waste Disposal: Dispose of waste in accordance with local, national, and institutional regulations for halogenated organic waste. Do not pour down the drain.
• Spill Management: In the event of a spill, contain with inert absorbent material, collect into a labelled waste container, and ventilate the area thoroughly.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use. The SDS contains authoritative hazard classification, first-aid measures, and disposal information specific to this product (SKU B124453).

Quality, Purity, and Analytical Verification

For research applications where reagent purity directly affects experimental outcomes—such as catalytic cross-coupling, biological assays, or structure–activity relationship (SAR) studies—it is essential to verify the identity and purity of 2-Bromo-5-nitrothiazole (SKU B124453) before use.

Certificate of Analysis (CoA): Aladdin Scientific provides a lot-specific CoA for each batch of B124453. Researchers should download and review the CoA, which typically includes purity (determined by HPLC or GC), melting point, and spectroscopic confirmation (e.g., NMR, MS).

Recommended In-House Checks:

• TLC or HPLC: Compare against an authentic standard or a previously characterised lot to confirm purity and the absence of common impurities (e.g., debrominated or reduced by-products).
• ¹H NMR: The compound is expected to show a characteristic aromatic singlet for the ring proton at C-4, consistent with the electron-deficient thiazole environment.
• Melting Point: Compare the observed melting point with the literature or CoA value as a rapid purity indicator.

If discrepancies in analytical data are observed, contact Aladdin Scientific technical support before proceeding with critical experiments.

Procurement and Ordering Information

2-Bromo-5-nitrothiazole is available from Aladdin Scientific under SKU B124453. Laboratory managers and procurement officers should note the following when ordering:

• Available Pack Sizes: Multiple pack sizes may be available to suit gram-scale synthesis or larger batch requirements. Contact Aladdin Scientific or visit the product page for current pack size options and pricing.
• Regulatory and Import Considerations: As a halogenated nitro compound, import regulations may apply in certain jurisdictions. Buyers are responsible for ensuring compliance with local import and hazardous-materials regulations.
• Lead Time: Standard stock items are typically dispatched promptly; consult the Aladdin Scientific website or your regional sales representative for real-time stock availability and lead times.
• Custom Quantities: For bulk or custom synthesis inquiries, contact Aladdin Scientific's custom synthesis team directly.

When placing an order, reference SKU B124453 to ensure correct product identification. A valid SDS and CoA are available upon request or for download from the Aladdin Scientific product page.

Frequently asked questions

What is 2-Bromo-5-nitrothiazole used for in organic synthesis?

2-Bromo-5-nitrothiazole is primarily used as a heterocyclic building block in nucleophilic aromatic substitution reactions, palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Sonogashira), and as a precursor for 2,5-disubstituted thiazole derivatives. Its electron-deficient ring system facilitates C–Br bond activation, and the nitro group can be reduced to an amine for further functionalization.

How should 2-Bromo-5-nitrothiazole be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location away from direct light, heat, oxidising agents, and strong acids or bases. Refer to the lot-specific Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for precise storage temperature recommendations for SKU B124453.

Can the nitro group of 2-Bromo-5-nitrothiazole be selectively reduced without affecting the C–Br bond?

Selective reduction of the nitro group in the presence of the C–Br bond is achievable using mild reducing systems such as iron powder in acetic acid (Fe/AcOH) or zinc in ammonium chloride (Zn/NH₄Cl). Catalytic hydrogenation conditions should be used cautiously, as they may also cleave the C–Br bond depending on catalyst and pressure. Reaction conditions should be optimised empirically for the desired selectivity.

Is 2-Bromo-5-nitrothiazole (SKU B124453) available with a Certificate of Analysis?

Yes. Aladdin Scientific provides a lot-specific Certificate of Analysis (CoA) for SKU B124453. The CoA is available for download from the product page or upon request from Aladdin Scientific customer service, and includes purity data, analytical test results, and physical characterisation.

What personal protective equipment is required when handling 2-Bromo-5-nitrothiazole?

Researchers should wear chemical-resistant gloves (e.g., nitrile), safety goggles, and a laboratory coat when handling this compound. All operations should be conducted in a well-ventilated fume hood to prevent inhalation of dust or vapours. Consult the SDS for full hazard and first-aid information before use.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for nucleophilic aromatic substitution and cross-coupling reactions.)
2. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for thiazole chemistry and reactivity.)
3. Aladdin Scientific. Product Page and Certificate of Analysis for 2-Bromo-5-nitrothiazole, SKU B124453. Retrieved from Aladdin Scientific official website.

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