Production Method 1

332883-48-4

84459-32-5

Reaction Conditions

1.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  rt; 24 h, rt

Reference

Axially Chiral Binaphthyl Surrogates with an Inner N-H-N Hydrogen Bond

Kawabata, Takeo; et al, Journal of the American Chemical Society, 2009, 131(1), 54-55

Production Method 2

332883-48-4

84459-32-5

Reaction Conditions

1.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 0 °C; 0 °C → rt; 3 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Enantioselective, Catalytic Vicinal Difluorination of Alkenes

Scheidt, Felix; et al, Angewandte Chemie, 2018, 57(50), 16431-16435

Production Method 3

943-14-6

84459-32-5

Reaction Conditions

1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 3 h, 0 °C; 12 h, 0 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water
1.3 Reagents: Dess-Martin periodinane Solvents: Water ;  1 h, rt

Reference

Hydrogen-Bonding Catalysis and Inhibition by Simple Solvents in the Stereoselective Kinetic Epoxide-Opening Spirocyclization of Glycal Epoxides to Form Spiroketals

Wurst, Jacqueline M.; et al, Journal of the American Chemical Society, 2011, 133(20), 7916-7925

Production Method 4

6630-33-7

84459-32-5

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Nitric acid ;  0 °C; 12 h, rt
1.2 Solvents: Water ;  0 °C

Reference

Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives

Yamada, Tsuyoshi ; et al, Organic Letters, 2020, 22(5), 1883-1888

Production Method 5

373622-95-8

84459-32-5

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ,  Tetrahydrofuran ;  1 h, -78 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  -78 °C

Reference

Discovery of a Highly Potent, Selective, and Orally Bioavailable Macrocyclic Inhibitor of Blood Coagulation Factor VIIa-Tissue Factor Complex

Zhang, Xiaojun; et al, Journal of Medicinal Chemistry, 2016, 59(15), 7125-7137

Production Method 6

6638-79-5

943-14-6

84459-32-5

Reaction Conditions

1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  20 min, 0 °C; 4 h, rt
1.2 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  10 min, 0 °C; 1 h, 0 °C; overnight, rt
2.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ,  Tetrahydrofuran ;  1 h, -78 °C
2.2 Reagents: Ammonium chloride Solvents: Water ;  -78 °C

Reference

Discovery of a Highly Potent, Selective, and Orally Bioavailable Macrocyclic Inhibitor of Blood Coagulation Factor VIIa-Tissue Factor Complex

Zhang, Xiaojun; et al, Journal of Medicinal Chemistry, 2016, 59(15), 7125-7137

Production Method 7

6942-36-5

84459-32-5

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C; -78 °C → 0 °C; 30 min, 0 °C; 0 °C → -78 °C
1.2 Reagents: Methanol ;  -78 °C
1.3 Reagents: Potassium sodium tartrate Solvents: Ethyl acetate ,  Water ;  2 h, rt
2.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  rt; 24 h, rt

Reference

Axially Chiral Binaphthyl Surrogates with an Inner N-H-N Hydrogen Bond

Kawabata, Takeo; et al, Journal of the American Chemical Society, 2009, 131(1), 54-55

Production Method 8

99-61-6

593-56-6

84459-32-5

Reaction Conditions

1.1 Reagents: Pyridine Solvents: Dichloromethane ;  1 h, rt
2.1 Reagents: N-Bromosuccinimide Catalysts: Silver trifluoroacetate ,  Palladium diacetate Solvents: 1,2-Dichloroethane ;  24 h, 120 °C
3.1 Reagents: Formaldehyde ,  p-Toluenesulfonic acid Solvents: Tetrahydrofuran ,  Water ;  15 min, 100 °C

Reference

Selective ortho-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C-H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes

Dubost, Emmanuelle; et al, Journal of Organic Chemistry, 2011, 76(15), 6414-6420

Production Method 9

943-14-6

84459-32-5

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  0 °C; 30 min, 0 °C; 0 °C → rt; 1 h, rt; rt → reflux; 3 h, reflux; reflux → rt
2.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C; -78 °C → 0 °C; 30 min, 0 °C; 0 °C → -78 °C
2.2 Reagents: Methanol ;  -78 °C
2.3 Reagents: Potassium sodium tartrate Solvents: Ethyl acetate ,  Water ;  2 h, rt
3.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  rt; 24 h, rt

Reference

Axially Chiral Binaphthyl Surrogates with an Inner N-H-N Hydrogen Bond

Kawabata, Takeo; et al, Journal of the American Chemical Society, 2009, 131(1), 54-55

Production Method 10

332883-48-4

84459-32-5

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: 1,10-Phenanthroline ,  Cuprous iodide Solvents: Toluene ;  7 - 48 h, 80 °C; 80 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Simple, Copper(I)-Catalyzed Oxidation of Benzylic/Allylic Alcohols to Carbonyl Compounds: Synthesis of Functionalized Cinnamates in One Pot

Reddy, Alavala Gopi Krishna; et al, Synthetic Communications, 2014, 44(14), 2076-2087

Production Method 11

943-14-6

84459-32-5

Reaction Conditions

1.1 Reagents: (Dimethyl sulfide)trihydroboron Solvents: Tetrahydrofuran ;  0 °C; 0 °C; 2 h, 0 °C; 22 h, rt
1.2 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  0 °C; 0 °C; 0 °C → rt; 3 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Enantioselective, Catalytic Vicinal Difluorination of Alkenes

Scheidt, Felix; et al, Angewandte Chemie, 2018, 57(50), 16431-16435

Production Method 12

943-14-6

84459-32-5

Reaction Conditions

1.1 Reagents: Borane
1.2 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane

Reference

Palladium-catalyzed carbonylative cyclization of Baylis-Hillman adducts. An efficient approach for the stereoselective synthesis of 3-alkenyl phthalides

Coelho, Fernando; et al, Tetrahedron, 2006, 62(18), 4563-4572

Production Method 13

84459-32-5

Reaction Conditions

1.1 Reagents: Formaldehyde ,  p-Toluenesulfonic acid Solvents: Tetrahydrofuran ,  Water ;  15 min, 100 °C

Reference

Selective ortho-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C-H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes

Dubost, Emmanuelle; et al, Journal of Organic Chemistry, 2011, 76(15), 6414-6420

Production Method 14

139194-79-9

84459-32-5

Reaction Conditions

1.1 Reagents: Cesium carbonate ,  Oxygen Catalysts: Zinc oxide (ZnO) ,  Copper oxide (CuO) ,  Gold Solvents: Water ;  120 min, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Novel metal oxide nanocomposite of Au/CuO-ZnO for recyclable catalytic aerobic oxidation of alcohols in water

Albadi, Jalal; et al, Catalysis Communications, 2014, 49, 1-5

Production Method 15

99-61-6

84459-32-5

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: 2-Trifluoromethyl-4-chloroaniline ,  Palladium diacetate Solvents: Trifluoroacetic acid ,  1,2-Dichloroethane ;  24 h, 60 °C

Reference

Palladium-catalyzed ortho-C(sp2)-H bromination of benzaldehydes via a monodentate transient directing group strategy

Yong, Qiyun; et al, Tetrahedron Letters, 2019, 60(46),

Production Method 16

84459-32-5

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Silver trifluoroacetate ,  Palladium diacetate Solvents: 1,2-Dichloroethane ;  24 h, 120 °C
2.1 Reagents: Formaldehyde ,  p-Toluenesulfonic acid Solvents: Tetrahydrofuran ,  Water ;  15 min, 100 °C

Reference

Selective ortho-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C-H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes

Dubost, Emmanuelle; et al, Journal of Organic Chemistry, 2011, 76(15), 6414-6420

Production Method 17

80887-01-0

6638-79-5

84459-32-5

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  10 min, 0 °C; 1 h, 0 °C; overnight, rt
2.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ,  Tetrahydrofuran ;  1 h, -78 °C
2.2 Reagents: Ammonium chloride Solvents: Water ;  -78 °C

Reference

Discovery of a Highly Potent, Selective, and Orally Bioavailable Macrocyclic Inhibitor of Blood Coagulation Factor VIIa-Tissue Factor Complex

Zhang, Xiaojun; et al, Journal of Medicinal Chemistry, 2016, 59(15), 7125-7137

2-Bromo-5-nitrobenzaldehyde Raw materials

• 3-Nitrobenzaldehyde
• Methoxyamine hydrochloride
• 2-Bromo-5-nitrobenzoic Acid Methyl Ester
• (2-Bromo-5-nitrophenyl)methanol
• (3-bromo-5-nitro-phenyl)methanol
• 2-Bromobenzaldehyde
• 2-Bromo-N-methoxy-N-methyl-5-nitrobenzamide
• 2-bromo-5-nitrobenzoyl chloride
• N,O-Dimethylhydroxylamine hydrochloride
• 2-Bromo-5-nitrobenzoic acid

2-Bromo-5-nitrobenzaldehyde Preparation Products

• 2-Bromo-5-nitrobenzaldehyde (84459-32-5)

• 1. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan
• 2. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555
• 3. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 4. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 5. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991

Comprehensive Overview of 2-Bromo-5-nitrobenzaldehyde (CAS No. 84459-32-5): Properties, Applications, and Industry Insights

2-Bromo-5-nitrobenzaldehyde (CAS No. 84459-32-5) is a specialized organic compound widely recognized for its versatile applications in pharmaceutical intermediates, agrochemical synthesis, and advanced material research. This yellow crystalline solid belongs to the class of nitrobenzaldehyde derivatives, characterized by the presence of both bromo and nitro functional groups on the benzene ring. Its molecular formula, C₇H₄BrNO₃, and unique structural features make it a valuable building block in modern organic chemistry.

The compound's electrophilic aromatic substitution reactivity, driven by the electron-withdrawing effects of the nitro group, enables its use in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig animations. Recent studies highlight its role in developing photoactive materials for OLEDs and bioconjugation probes for biochemical assays. With growing interest in sustainable synthesis methods, researchers are exploring catalytic approaches to optimize the production of 2-Bromo-5-nitrobenzaldehyde while minimizing environmental impact.

In pharmaceutical contexts, this compound serves as a precursor for antimicrobial agents and kinase inhibitors, aligning with current trends in targeted drug discovery. Analytical techniques like HPLC purity analysis (typically >98%) and FT-IR spectroscopy are essential for quality control, particularly when the material is used in GMP-compliant synthesis. The global market for nitroaromatic compounds shows steady growth, projected at 4.2% CAGR through 2030, driven by demand from Asia-Pacific pharmaceutical manufacturers.

Handling 2-Bromo-5-nitrobenzaldehyde requires standard laboratory precautions due to its potential photosensitivity and moderate solubility profile (soluble in DMSO, DMF; sparingly soluble in water). Storage recommendations include amber glass containers at 2-8°C under inert atmosphere to prevent oxidative degradation. These stability considerations are particularly relevant for researchers working on long-term stability studies of derivative compounds.

Emerging applications in materials science leverage the compound's ability to form Schiff base ligands for transition metal complexes. This has sparked interest in developing molecular sensors for environmental monitoring, especially for heavy metal detection. The compound's X-ray crystallography data (CCDC deposition numbers available) provides valuable structural insights for computational chemists developing QSAR models of related aromatic aldehydes.

From a regulatory perspective, 2-Bromo-5-nitrobenzaldehyde is not classified under restricted categories, though proper SDS documentation should always accompany shipments. Suppliers typically offer technical and analytical grade variants, with pricing influenced by purity levels and batch scalability. Recent patent analyses reveal increasing use of this compound in heterocyclic synthesis, particularly for benzimidazole scaffolds with potential therapeutic applications.

The synthesis route typically involves bromination of 5-nitrobenzaldehyde using NBS or molecular bromine, with yields optimized through microwave-assisted synthesis techniques. Process chemists emphasize the importance of reaction monitoring via TLC or GC-MS to control byproduct formation. These methodological advancements address the pharmaceutical industry's need for cost-effective intermediates in multi-step syntheses.

Environmental fate studies indicate that 2-Bromo-5-nitrobenzaldehyde undergoes aerobic biodegradation in soil systems (half-life ≈ 14-28 days), with photodegradation being the primary pathway in aquatic environments. These findings support its inclusion in green chemistry initiatives when proper waste management protocols are followed. The compound's EC50 values in standard ecotoxicity assays confirm it requires standard industrial handling precautions.

For researchers sourcing this chemical, key specifications include melting point (typically 98-102°C), residual solvent levels (meeting ICH Q3C guidelines), and heavy metal content (typically <10 ppm). These parameters are critical for applications in cGMP manufacturing where impurity profiles directly impact downstream reactions. Leading suppliers now provide certificates of analysis with detailed chromatographic purity data and NMR verification.

Future research directions focus on developing continuous flow processes for its production and exploring its potential in click chemistry applications. The compound's balanced lipophilicity (calculated logP ≈ 1.8) makes it particularly interesting for medicinal chemistry applications requiring blood-brain barrier penetration. These developments position 2-Bromo-5-nitrobenzaldehyde as a compound of continuing significance in synthetic organic chemistry.

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