Production Method 1

823-78-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetonitrile ;  13 min, 60 °C

Reference

A Scalable Procedure for Light-Induced Benzylic Brominations in Continuous Flow

Cantillo, David; et al, Journal of Organic Chemistry, 2014, 79(1), 223-229

Production Method 2

823-78-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Benzoyl peroxide Solvents: Carbon tetrachloride ;  reflux

Reference

Design, synthesis and biological evaluation of low molecular weight CXCR4 ligands

Sakyiamah, Maxwell M.; et al, Bioorganic & Medicinal Chemistry, 2019, 27(6), 1130-1138

Production Method 3

1878-67-7

823-78-9

Reaction Conditions

1.1 Reagents: Dibromoisocyanuric acid Catalysts: Silver(1+), bis(1,10-phenanthroline-κN1,κN10)-, (T-4)-, 1,1,1-trifluoromethanesu… Solvents: 1,2-Dichloroethane ;  1 h, rt

Reference

Silver-Catalyzed Decarboxylative Bromination of Aliphatic Carboxylic Acids

Tan, Xinqiang; et al, Organic Letters, 2017, 19(7), 1634-1637

Production Method 4

15852-73-0

823-78-9

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Toluene ;  0 - 5 °C; 30 min, rt; 2 h, 100 °C

Reference

Development of Chromen-4-one Derivatives as (Ant)agonists for the Lipid-Activated G Protein-Coupled Receptor GPR55 with Tunable Efficacy

Schoeder, Clara T.; et al, ACS Omega, 2019, 4(2), 4276-4295

Production Method 5

585-76-2

823-78-9

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  30 min, > rt; 4 h, rt
1.2 Reagents: Sulfuric acid Solvents: Water ;  0 - 5 °C
2.1 Reagents: Phosphorus tribromide Solvents: Toluene ;  0 - 5 °C; 30 min, rt; 2 h, 100 °C

Reference

Development of Chromen-4-one Derivatives as (Ant)agonists for the Lipid-Activated G Protein-Coupled Receptor GPR55 with Tunable Efficacy

Schoeder, Clara T.; et al, ACS Omega, 2019, 4(2), 4276-4295

Production Method 6

823-78-9

585-76-2

Reaction Conditions

Reference

Synthesis by substitution of hydrogen

Pfeiffer, W. D., Science of Synthesis, 2007, 35, 391-408

Production Method 7

15852-73-0

823-78-9

932-77-4

Reaction Conditions

1.1 Reagents: Cyanuric chloride Solvents: Dimethylformamide ;  25 °C
1.2 Reagents: Sodium bromide Solvents: Dichloromethane ;  10 h, 25 °C
1.3 25 min, rt

Reference

A chemoselective, easy bromination of (hydroxymethyl)phenols

Nieddu, Giammario; De Luca, Lidia; Giacomelli, Giampaolo, Synthesis, 2008, (24), 3937-3940

Production Method 8

823-78-9

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  3.5 h, reflux

Reference

Synthesis and bioactivity of some imidazole- and triazole-ether compounds

Li, Zai-feng; et al, Jingxi Huagong, 2005, 22(8), 619-624

Production Method 9

15852-73-0

823-78-9

Reaction Conditions

1.1 Reagents: Tetrabutylammonium iodide ,  Triphenylphosphine Solvents: 1,2-Dibromoethane ;  2 h, 60 °C

Reference

Halogenation through Deoxygenation of Alcohols and Aldehydes

Chen, Jia; et al, Organic Letters, 2018, 20(10), 3061-3064

Production Method 10

15852-73-0

823-78-9

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  0 °C; 2 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Synthesis and Biological Evaluation of Small Molecules as Potential Anticancer Multitarget Agents

Pla-Lopez, Alberto; et al, International Journal of Molecular Sciences, 2022, 23(13),

Production Method 11

3132-99-8

823-78-9

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt; 30 min, rt
2.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  15 min, 0 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Synthesis of α-Aryldiazophosphonates via a Diazo Transfer Reaction

Beletskaya, Irina P.; et al, Journal of Organic Chemistry, 2022, 87(5), 2748-2757

3-Bromobenzyl bromide Raw materials

• 3-Bromobenzaldehyde
• 3-Bromobenzyl alcohol
• 3-Bromobenzoic acid
• 3-Bromophenylacetic acid

3-Bromobenzyl bromide Preparation Products

• 3-Bromobenzyl bromide (823-78-9)
• 3-Bromobenzoic acid (585-76-2)
• 3-Bromobenzyl chloride (932-77-4)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyl halides Benzyl bromides

Professional Introduction to 3-Bromobenzyl bromide (CAS No. 823-78-9)

3-Bromobenzyl bromide, with the chemical formula C₇H₅Br₃, is a significant compound in the realm of organic synthesis and pharmaceutical research. This compound, identified by its unique CAS number 823-78-9, has garnered considerable attention due to its versatile applications in the development of novel drugs and agrochemicals. The presence of both bromine atoms and a benzyl group makes it a valuable intermediate in various synthetic pathways, particularly in the construction of more complex molecular structures.

The utility of 3-Bromobenzyl bromide stems from its reactivity, which allows for facile functionalization at multiple sites. This property is particularly advantageous in medicinal chemistry, where the ability to introduce specific functional groups is crucial for optimizing drug efficacy and pharmacokinetic profiles. Researchers have leveraged this compound to synthesize a range of derivatives that exhibit promising biological activities.

In recent years, there has been a surge in interest regarding the application of 3-Bromobenzyl bromide in the synthesis of small-molecule inhibitors targeting various disease pathways. For instance, studies have demonstrated its role in developing inhibitors for enzymes involved in cancer metabolism. The benzyl bromide moiety serves as a key structural feature that enhances binding affinity and selectivity, making it an indispensable tool for medicinal chemists.

Moreover, the compound has found utility in the field of material science, particularly in the synthesis of polymers and specialty chemicals. Its ability to undergo cross-coupling reactions with various organic substrates has enabled the creation of novel materials with tailored properties. These materials find applications in electronics, coatings, and even biodegradable polymers.

The synthetic versatility of 3-Bromobenzyl bromide is further highlighted by its role in constructing complex heterocyclic compounds. Heterocycles are a cornerstone of modern pharmaceuticals, often serving as the core structure for bioactive molecules. The introduction of bromine atoms into these structures allows for further derivatization via palladium-catalyzed reactions, such as Suzuki-Miyaura couplings, which are pivotal in constructing biaryl systems prevalent in many drugs.

Recent advancements in green chemistry have also seen the adoption of 3-Bromobenzyl bromide in more sustainable synthetic protocols. Efforts to minimize waste and reduce hazardous byproducts have led to innovative methodologies that leverage this compound's reactivity while adhering to environmental standards. Such approaches are increasingly important as the pharmaceutical industry moves towards more eco-friendly practices.

The biological activity of derivatives derived from 3-Bromobenzyl bromide has been extensively studied. Researchers have identified several compounds derived from this scaffold that exhibit inhibitory effects on enzymes such as kinases and phosphodiesterases. These enzymes are often implicated in various diseases, including cancer and inflammatory disorders. The benzyl bromide group facilitates the introduction of bulky substituents that can modulate enzyme active sites, leading to improved therapeutic outcomes.

In conclusion, 3-Bromobenzyl bromide (CAS No. 823-78-9) is a multifaceted compound with broad applications across organic synthesis and pharmaceutical research. Its unique structural features and reactivity make it an invaluable intermediate for constructing complex molecules with significant biological activity. As research continues to evolve, it is likely that new applications for this compound will emerge, further solidifying its importance in both academic and industrial settings.

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