1,3-Dibromo-5-nitrobenzene: Properties, Uses & FAQs

1,3-Dibromo-5-nitrobenzene is a symmetrically substituted aromatic building block bearing two bromo leaving groups and an electron-withdrawing nitro group, making it a versatile intermediate for cross-coupling reactions, materials science, and pharmaceutical synthesis.

Chemical Name

1,3-Dibromo-5-nitrobenzene

SKU / Catalog Number

D171254

Molecular Formula

C₆H₃Br₂NO₂

Molecular Weight

280.90 g/mol

CAS Number

6311-60-0

Symmetry

C₂ᵥ symmetry; nitro group at position 5, bromo groups at positions 1 and 3

Key Application

Difunctional aryl halide for Suzuki, Negishi, and Buchwald-Hartwig cross-coupling reactions

Chemical Identity and Structure

1,3-Dibromo-5-nitrobenzene (CAS 6311-60-0, MW 280.90 g/mol, molecular formula C₆H₃Br₂NO₂) is a trisubstituted benzene derivative in which two bromine atoms occupy the 1- and 3-positions while a nitro group sits at the 5-position. This arrangement confers C₂ᵥ symmetry on the molecule and places both C–Br bonds in electronically equivalent environments, a property that simplifies reaction planning when both sites are to be functionalized sequentially or simultaneously.

The electron-withdrawing nitro group activates the ring toward nucleophilic aromatic substitution and simultaneously deactivates it toward electrophilic aromatic substitution. In cross-coupling chemistry, the nitro substituent increases the electrophilicity of the aryl–halide bond, which can facilitate oxidative addition of palladium(0) catalysts.

Synthetic Applications and Reactivity

The two aryl bromide handles of 1,3-Dibromo-5-nitrobenzene make it a valuable difunctional building block in modern synthetic chemistry. Key reaction types include:

• Suzuki–Miyaura coupling: Reaction with aryl- or vinyl boronic acids in the presence of a Pd catalyst and base yields biaryl or styryl products, enabling construction of extended π-conjugated frameworks useful in organic electronics and supramolecular chemistry.
• Negishi coupling: Use of organozinc partners under Pd catalysis provides access to diverse aryl–aryl and aryl–alkyl architectures.
• Buchwald–Hartwig amination: The compound serves as a substrate for Pd-catalyzed C–N bond formation, enabling the preparation of diarylamine-containing motifs relevant to pharmaceutical and materials research.
• Sonogashira coupling: Reaction with terminal alkynes installs alkynyl arms at both positions, producing bis-alkynyl arenes for use in molecular wires and functional materials.
• Reduction of the nitro group: Selective reduction (e.g., with Fe/AcOH, H₂/Pd-C, or SnCl₂) affords the corresponding 3,5-dibromoaniline, a further versatile intermediate.

The symmetric nature of the compound allows either mono- or di-functionalization strategies, providing synthetic flexibility in target-oriented synthesis.

Handling, Storage, and Safety

When working with 1,3-Dibromo-5-nitrobenzene, researchers should observe standard laboratory safety practices for halogenated aromatic nitro compounds:

• Personal protective equipment: Wear chemical-resistant gloves, a laboratory coat, and safety glasses. Use a fume hood for all weighing and reaction operations to avoid inhalation of dust or vapors.
• Storage: Store the compound in a tightly sealed container in a cool, dry, well-ventilated area, away from reducing agents, flammable materials, and strong acids or bases. Typical recommended storage is at room temperature unless the supplier's certificate of analysis specifies otherwise.
• Waste disposal: Dispose of waste in accordance with applicable local, regional, and national regulations for halogenated organic waste. Do not discharge into drains or water systems.
• First aid: In case of skin or eye contact, rinse with copious amounts of water and seek medical advice. If inhaled, move to fresh air immediately.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific (SKU D171254) before first use for compound-specific hazard information, GHS classifications, and emergency procedures.

Purity, Quality, and Specification

Aladdin Scientific supplies 1,3-Dibromo-5-nitrobenzene (SKU D171254) as a research-grade reagent. Typical quality parameters evaluated for this class of compound include:

• Purity: Assessed by GC or HPLC analysis. Research-grade material is generally ≥97% or ≥98% purity; refer to the current Certificate of Analysis (CoA) available on the Aladdin Scientific product page for the lot-specific value.
• Appearance: Off-white to pale yellow crystalline solid.
• Identity confirmation: Verified by techniques such as ¹H NMR, ¹³C NMR, or mass spectrometry. The ¹H NMR spectrum of 1,3-Dibromo-5-nitrobenzene in CDCl₃ shows two distinct singlet signals consistent with the two types of aromatic protons in a 2:1 ratio.
• Melting point: Literature values for this compound are reported in the range of approximately 97–103 °C; consult the CoA for the confirmed lot value.

For critical applications, customers are encouraged to request the current CoA at the time of order to verify lot-specific analytical data.

Frequently Ordered Alongside and Related Products

Researchers working with 1,3-Dibromo-5-nitrobenzene typically require complementary reagents such as palladium catalysts (e.g., Pd(PPh₃)₄, Pd(dppf)Cl₂), phosphine ligands, organoboron coupling partners, and inorganic bases (e.g., K₂CO₃, Cs₂CO₃) for cross-coupling workflows. Reducing agents such as iron powder, tin(II) chloride, or palladium on carbon may be needed for nitro group reduction.

Related halogenated arene building blocks available from Aladdin Scientific may include other dibromonitrobenzene isomers, bromonitrobenzene derivatives, and related aryl halide intermediates. Please browse the Aladdin Scientific catalog or contact our technical support team for current availability and pricing.

Frequently asked questions

What is 1,3-Dibromo-5-nitrobenzene used for in organic synthesis?

1,3-Dibromo-5-nitrobenzene is primarily used as a difunctional aryl halide building block in transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and Sonogashira couplings. Its two equivalent C–Br bonds allow mono- or di-functionalization, making it valuable for constructing branched or star-shaped π-conjugated architectures used in organic electronics, supramolecular chemistry, and pharmaceutical intermediate synthesis. The nitro group can also be selectively reduced to an amine, further expanding synthetic utility.

How should 1,3-Dibromo-5-nitrobenzene be stored to maintain stability?

1,3-Dibromo-5-nitrobenzene should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from incompatible materials such as strong reducing agents, strong acids, strong bases, and flammable substances. Under these conditions the compound is expected to be stable for an extended period. Always refer to the current Safety Data Sheet (SDS) and Certificate of Analysis from Aladdin Scientific (SKU D171254) for lot-specific storage recommendations.

What is the CAS number and molecular formula of 1,3-Dibromo-5-nitrobenzene?

The CAS registry number of 1,3-Dibromo-5-nitrobenzene is 6311-60-0, its molecular formula is C₆H₃Br₂NO₂, and its molecular weight is 280.90 g/mol. These identifiers can be used to confirm the compound identity against the Certificate of Analysis and spectral databases.

Can both bromine atoms in 1,3-Dibromo-5-nitrobenzene be functionalized independently?

In principle, selective mono-functionalization of one C–Br bond is possible but challenging because both bromines are electronically equivalent due to the molecule's C₂ᵥ symmetry. Statistical mixtures of mono- and di-functionalized products are commonly obtained under standard cross-coupling conditions. Sequential functionalization with differentiated coupling partners or careful stoichiometric control can be used to favor the mono-substituted product. For full di-functionalization, both bromines can be engaged with the same or different coupling partners in one-pot or sequential reaction sequences.

What purity grade is the Aladdin Scientific D171254 product, and how is purity verified?

Aladdin Scientific supplies 1,3-Dibromo-5-nitrobenzene (SKU D171254) as a research-grade reagent; purity is typically assessed by GC or HPLC analysis. The lot-specific purity value is reported on the Certificate of Analysis (CoA) available on the product page or upon request. Customers requiring confirmation of compound identity may additionally verify by ¹H NMR, ¹³C NMR, or mass spectrometry against known spectral data.

References

1. CAS Registry: 1,3-Dibromo-5-nitrobenzene, CAS RN 6311-60-0. SciFinder / CAS databases.
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
3. Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholz, U. Industrial-Scale Palladium-Catalyzed Coupling of Aryl Chlorides and Amines — A Personal Account. Adv. Synth. Catal. 2006, 348, 23–39.
4. Aladdin Scientific Certificate of Analysis, SKU D171254, 1,3-Dibromo-5-nitrobenzene. Available from Aladdin Scientific product page.

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