Production Method 1

6967-82-4

90221-55-9

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  cooled; 15 min, cooled
1.2 Reagents: Boron trifluoride etherate ;  cooled; 1 h, 60 °C
1.3 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane ;  rt; overnight, rt

Reference

Intriguing substituent effect in modified Hoveyda-Grubbs metathesis catalysts incorporating a chelating iodo-benzylidene ligand

Barbasiewicz, Michal; Blocki, Krzysztof; Malinska, Maura; Pawlowski, Robert, Dalton Transactions, 2013, 42(2), 355-358

Production Method 2

870-63-3

959687-83-3

90221-55-9

Reaction Conditions

1.1 Reagents: Magnesate(1-), chlorobis(1-methylethyl)-, lithium (1:1) Solvents: Tetrahydrofuran ,  1,4-Dioxane ;  24 h, rt
1.2 Solvents: Tetrahydrofuran ;  rt; 12 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  rt; 15 min, rt

Reference

AuCl3-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis

Wang, Rui ; Chen, Yi; Shu, Mao; Zhao, Wenwen; Tao, Maoling; et al, Chemistry - A European Journal, 2020, 26(9), 1941-1946

Production Method 3

6967-82-4

90221-55-9

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.; Liu, Guodong; Tan, Derek S., Journal of the American Chemical Society, 2011, 133(20), 7916-7925

Production Method 4

27561-50-8

90221-55-9

Reaction Conditions

1.1 Reagents: Potassium bicarbonate Solvents: Dimethyl sulfoxide ;  overnight, 80 °C

Reference

Formal asymmetric hydrobromination of styrenes via copper-catalyzed 1,3-halogen migration

Van Hoveln, R. J.; Schmid, S. C.; Tretbar, M.; Buttke, C. T.; Schomaker, J. M., Chemical Science, 2014, 5(12), 4763-4767

Production Method 5

727985-37-7

90221-55-9

Reaction Conditions

1.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane

Reference

[5]Helicene-based chiral triarylboranes with large luminescence dissymmetry factors over a 10-2 level: synthesis and design strategy via isomeric tuning of steric substitutions

Zhao, Fei; Zhao, Jingyi; Wang, Yu; Liu, Hou-Ting; Shang, Qinghai; et al, Dalton Transactions, 2022, 51(16), 6226-6234

Production Method 6

42872-83-3

90221-55-9

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Toluene ;  0 °C; 0 °C → 45 °C; 12 h, 45 °C; 45 °C → rt
1.2 Reagents: Methanol Solvents: Toluene

Reference

Palladium-Catalyzed Ring-Forming Aminoalkenylation of Alkenes with Aldehydes Initiated by Intramolecular Aminopalladation

Hu, Yue; Xie, Yinjun; Shen, Zhiqiang; Huang, Hanmin, Angewandte Chemie, 2017, 56(9), 2473-2477

2-Bromo-5-methylbenzaldehyde Raw materials

• 2-Bromo-5-methylbenzonitrile
• 2-Bromo-5-methylbenzoic acid
• (2-bromo-5-methylphenyl)methanol
• 1-Bromo-2-(bromomethyl)-4-methylbenzene
• 1-bromo-3-methyl-but-2-ene
• Benzene, 1-bromo-2-(dimethoxymethyl)-4-methyl-

2-Bromo-5-methylbenzaldehyde Preparation Products

• 2-Bromo-5-methylbenzaldehyde (90221-55-9)

• 1. Dimethylnonacethrene – en route to a magnetic switch
  Daniel ?avlovi?,Olivier Blacque,Ivo Krummenacher,Holger Braunschweig,Prince Ravat,Michal Jurí?ek Chem. Commun. 2023 59 7743

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

Introduction to CAS No. 90221-55-9: 2-Bromo-5-Methylbenzaldehyde

2-Bromo-5-methylbenzaldehyde, also known by its CAS registry number 90221-55-9, is a versatile organic compound with significant applications in various fields of chemistry. This compound is characterized by its unique structure, which combines a bromine atom at the second position and a methyl group at the fifth position on the benzene ring, along with an aldehyde functional group. The combination of these substituents imparts distinctive chemical properties, making it a valuable molecule in both academic research and industrial applications.

The synthesis of 2-bromo-5-methylbenzaldehyde typically involves multi-step organic reactions, often utilizing directing groups and protecting strategies to achieve the desired substitution pattern. Recent advancements in catalytic methods and green chemistry have enabled more efficient and environmentally friendly syntheses of this compound. For instance, researchers have explored the use of transition metal catalysts to facilitate the bromination and alkylation steps, reducing reaction times and minimizing byproducts.

In terms of chemical properties, 2-bromo-5-methylbenzaldehyde exhibits moderate solubility in common organic solvents such as dichloromethane and ethyl acetate, while being relatively insoluble in water. Its aldehyde group makes it reactive towards nucleophilic additions, a property that has been exploited in various synthetic transformations. For example, recent studies have demonstrated its utility as a precursor in the synthesis of heterocyclic compounds, which are of great interest in drug discovery.

The applications of 2-bromo-5-methylbenzaldehyde span across multiple domains. In the pharmaceutical industry, it serves as an intermediate in the synthesis of bioactive molecules targeting various therapeutic areas such as cancer and inflammation. Its bromine substituent facilitates Suzuki-Miyaura coupling reactions, enabling the construction of complex molecular architectures. Moreover, its methyl group provides steric bulk, which can influence the pharmacokinetic properties of derived compounds.

In materials science, 2-bromo-5-methylbenzaldehyde has been employed as a building block for the preparation of advanced materials such as polymers and coordination complexes. Its ability to undergo cross-coupling reactions makes it a valuable component in the design of functional materials with tailored properties. Recent research has highlighted its potential in creating stimuli-responsive materials that can adapt to environmental changes, opening new avenues for smart technologies.

The study of 2-bromo-5-methylbenzaldehyde has also contributed to our understanding of aromatic substitution patterns and reactivity trends. Its structure serves as a model system for investigating how substituents influence electronic effects and steric interactions on aromatic rings. Such insights are crucial for designing new molecules with desired reactivity profiles.

In conclusion, CAS No. 90221-55-9 (2-bromo-5-methylbenzaldehyde) is a multifaceted compound with wide-ranging applications in chemistry and related disciplines. Its unique structure and reactivity continue to inspire innovative research directions, underscoring its importance as a key building block in modern chemical synthesis.

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• 6630-33-7(2-Bromobenzaldehyde)
• 5629-98-1(2,4-Dibromobenzaldehyde)
• 400822-47-1(4-Bromo-3,5-dimethylbenzaldehyde)
• 824-54-4(2-Bromo-4-methylbenzaldehyde)
• 36276-24-1(3-Bromo-4-methylbenzaldehyde)
• 3378-82-3(1-Bromo-2-naphthaldehyde)
• 79839-49-9(2-bromobenzene-1,3-dicarbaldehyde)
• 78775-11-8(4-Bromo-3-methylbenzaldehyde)