Production Method 1

97456-81-0

83647-40-9

Reaction Conditions

1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Dimethylformamide ;  2 h, rt
1.2 Reagents: Triethylamine Catalysts: Tris(dibenzylideneacetone)dipalladium ;  6 h, 70 °C

Reference

Use of Carbonyldiimidazole as an Activator of Formic Acid in a Tris(dibenzylideneacetone)dipalladium-Catalyzed Formylation of Aryl Iodides

Nadhagopal, Sundar; et al, Synlett, 2023, 34(15), 1809-1813

Production Method 2

529-20-4

83647-40-9

90050-59-2

Reaction Conditions

1.1 Reagents: Hydrogen tribromide, compd. with 1-methyl-1H-imidazole (1:1) ;  21 h, 70 °C

Reference

Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromide as reagent/solvent

Chiappe, Cinzia; et al, Chemical Communications (Cambridge, 2004, (22), 2536-2537

Production Method 3

69321-60-4

83647-40-9

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C
1.2 30 min, -78 °C; 1 h, -78 °C → 0 °C
1.3 Reagents: Water

Reference

Addition of Fluorine and a Late-Stage Functionalization (LSF) of the Oral SERD AZD9833

Scott, James S. ; et al, ACS Medicinal Chemistry Letters, 2020, 11(12), 2519-2525

Production Method 4

76006-33-2

83647-40-9

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride
1.2 Reagents: Manganese oxide (MnO2)

Reference

Regioselective Functionalization of 4-Methyl-1H-indole for Scalable Synthesis of 2-Cyano-5-formyl-4-methyl-1H-indole

Zhang, Jun; et al, Organic Process Research & Development, 2018, 22(1), 97-102

3-Bromo-2-methylbenzaldehyde Raw materials

• 1,3-dibromo-2-methylbenzene
• 3-bromo-2-methyl-benzoic acid
• 1-Bromo-3-iodo-2-methylbenzene
• 2-Methylbenzaldehyde

3-Bromo-2-methylbenzaldehyde Preparation Products

• 3-Bromo-2-methylbenzaldehyde (83647-40-9)
• 5-Bromo-2-methylbenzaldehyde (90050-59-2)

• 1. Fate of single walled carbon nanotubes in wetland ecosystems?
  Joseph H. Bisesi,Tara Sabo-Attwood Environ. Sci.: Nano, 2014,1, 574-583
• 2. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119
• 3. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 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. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives

Properties and Applications of 3-Bromo-2-methylbenzaldehyde (CAS No. 83647-40-9)

3-Bromo-2-methylbenzaldehyde, with the chemical formula C?H?BrO, is a halogenated aromatic aldehyde that has garnered significant attention in the field of organic synthesis and pharmaceutical research. This compound, identified by its CAS number 83647-40-9, serves as a versatile intermediate in the synthesis of various biologically active molecules. Its unique structural features, combining a bromine substituent with a methyl group on a benzene ring and an aldehyde functional group, make it a valuable building block for medicinal chemistry applications.

The 3-Bromo-2-methylbenzaldehyde molecule exhibits distinct chemical properties that facilitate its use in synthetic pathways. The presence of the bromine atom at the 3-position enhances its reactivity in cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are pivotal in constructing complex molecular architectures. Additionally, the methyl group at the 2-position influences the electronic distribution of the aromatic ring, affecting its interaction with other functional groups during synthesis.

In recent years, 3-Bromo-2-methylbenzaldehyde has been explored in the development of novel pharmaceuticals. Its aldehyde functionality allows for condensation reactions with various nucleophiles, including amines and hydrazines, leading to imines and hydrazones respectively. These derivatives have shown promise in preliminary studies as intermediates for drugs targeting neurological disorders. For instance, researchers have utilized derivatives of 3-Bromo-2-methylbenzaldehyde to synthesize small molecules that modulate enzyme activity associated with neurodegenerative diseases.

Moreover, the compound has found applications in agrochemical research. The structural motif of 3-Bromo-2-methylbenzaldehyde is reminiscent of several natural products known for their pesticidal and herbicidal properties. By leveraging its reactivity, chemists have designed analogs that exhibit enhanced efficacy against plant pathogens while maintaining environmental safety. Such efforts align with global trends toward sustainable agriculture and the development of next-generation crop protection agents.

The synthesis of 3-Bromo-2-methylbenzaldehyde typically involves bromination and formylation reactions starting from commercially available precursors like toluene or xylene derivatives. Advanced synthetic methodologies, including catalytic hydrogenation and metal-catalyzed coupling reactions, have been optimized to improve yield and purity. These advancements underscore the compound's importance as a synthetic intermediate in industrial-scale production.

Recent studies have also highlighted the role of 3-Bromo-2-methylbenzaldehyde in material science. Its ability to participate in polymerization reactions makes it a candidate for developing novel functional materials. For example, researchers have incorporated it into polymer backbones to create materials with enhanced thermal stability or luminescent properties. Such innovations open doors to applications in electronics, coatings, and specialty plastics.

In conclusion, 3-Bromo-2-methylbenzaldehyde (CAS No. 83647-40-9) is a multifaceted compound with broad utility across pharmaceuticals, agrochemicals, and material science. Its unique structural features enable diverse synthetic transformations, making it indispensable in modern chemical research. As scientific understanding progresses, further applications of this compound are expected to emerge, reinforcing its significance in advancing chemical innovation.

• 24078-12-4(4-bromo-2-methyl-benzaldehyde)
• 88174-55-4(Benzaldehyde, 5-bromo-2,3,4-trimethyl-)
• 88174-52-1(Benzaldehyde, 3-bromo-2,4,5,6-tetramethyl-)
• 88174-44-1(4-bromo-2,3,5,6-tetramethylbenzaldehyde)
• 88174-34-9(Benzaldehyde, 2-bromo-3,4,5,6-tetramethyl-)
• 88174-27-0(Benzaldehyde, 3-bromo-2,4,6-trimethyl-)
• 36276-24-1(3-Bromo-4-methylbenzaldehyde)
• 88174-53-2(Benzaldehyde, 2-bromo-4,6-dimethyl-)
• 88174-38-3(Benzaldehyde, 6-bromo-2,3,4-trimethyl-)
• 88111-74-4(4-Bromo-2,5-dimethylbenzaldehyde)