2-Bromo-4,5-dimethoxybenzyl bromide
[CAS# 53207-00-4]

Identification

• Classification: Organic raw materials >> Aryl compounds
• Name: 2-Bromo-4,5-dimethoxybenzyl bromide
• Synonyms: 1-Bromo-2-(bromomethyl)-4,5-dimethoxybenzene; 1-Bromo-2-bromomethyl-4,5-dimethoxybenzene
• Molecular Formula: C₉H₁₀Br₂O₂
• Molecular Weight: 309.98
• CAS Registry Number: 53207-00-4
• EC Number: 610-978-6
• SMILES: COC1=C(C=C(C(=C1)CBr)Br)OC

Properties

• Solubility: Very slightly soluble (0.2 g/L) (25 ºC), Calc.^*
• Density: 1.692±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Melting point: 84.0-85.5 ºC^**
• Boiling point: 320.6±37.0 ºC (760 Torr), Calc.^*
• Flash point: 129.6±25.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

^** Ma, Hong Min; Chinese Chemical Letters 2003, V14(4), P371-374.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H312-H314-H315-H317-H319-H332-H335
• Precautionary Statements: P260-P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Skin corrosion	Skin Corr.	1	H314
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

2-Bromo-4,5-dimethoxybenzyl bromide is a chemical compound that belongs to the class of organobromine compounds, characterized by the presence of two bromine atoms and methoxy groups attached to a benzene ring. It is primarily used in organic synthesis due to its versatile reactivity and the role it plays as an important intermediate in the synthesis of other chemical compounds.

The discovery of 2-bromo-4,5-dimethoxybenzyl bromide is linked to the broader field of halogenated aromatic compounds, which have been well studied for their utility in the synthesis of various organic materials. The compound is typically synthesized through bromination reactions involving the appropriate precursor molecules, with the positioning of the bromine atoms on the benzene ring achieved through careful control of reaction conditions.

2-Bromo-4,5-dimethoxybenzyl bromide is an important intermediate in the synthesis of other organic compounds, particularly those containing the benzyl group or the dimethoxy group. These groups are valuable for modifying the chemical and physical properties of the final product, and their presence makes the compound a useful building block in the production of more complex molecules. The compound’s ability to participate in nucleophilic substitution reactions and its reactivity in electrophilic aromatic substitution reactions further enhance its utility in synthetic organic chemistry.

In organic synthesis, 2-bromo-4,5-dimethoxybenzyl bromide is used as a reagent in the preparation of various bioactive molecules and pharmaceutical intermediates. It plays a critical role in the synthesis of substituted aromatic compounds, which have potential applications in the development of therapeutic agents. For instance, compounds derived from this molecule may possess properties useful for anti-inflammatory, antimicrobial, or anticancer applications. The bromine atoms in 2-bromo-4,5-dimethoxybenzyl bromide enable the molecule to undergo various transformations, making it a valuable tool in medicinal chemistry.

Moreover, the compound is employed in the synthesis of functionalized materials, including those used in the field of materials science. Its reactivity allows for the introduction of specific functional groups into polymers or other material matrices, leading to the development of new materials with tailored properties. This characteristic has made 2-bromo-4,5-dimethoxybenzyl bromide useful in the creation of advanced materials with applications in electronics, coatings, and composites.

In addition to its synthetic and material applications, 2-bromo-4,5-dimethoxybenzyl bromide has been utilized in the study of reaction mechanisms and catalysis. The compound’s ability to undergo halogen exchange and substitution reactions has made it a subject of interest for researchers investigating the kinetics and mechanisms of these types of reactions. The use of 2-bromo-4,5-dimethoxybenzyl bromide in catalytic processes has contributed to a better understanding of the behavior of halogenated aromatic compounds in organic transformations.

In summary, 2-bromo-4,5-dimethoxybenzyl bromide is an important intermediate in organic synthesis with applications in the pharmaceutical, materials, and chemical industries. Its reactivity and versatile nature make it a key reagent for the preparation of bioactive compounds, functionalized materials, and complex organic molecules. The compound’s contribution to the development of new materials and its use in the study of chemical reaction mechanisms further demonstrate its value in both industrial and academic research.

References

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DOI: 10.1002/hlca.201900167

2015. Synthesis of 2-Benzylbenzimidazole and 2-Benzylbenzothiazole Derivatives. Helvetica Chimica Acta, 98(5).
DOI: 10.1002/hlca.201400312

2010. Synthesis of 2-Benzylbenzoxazole and 2-Benzylbenzothiazole Derivatives via a One-Pot Reaction of o-Aminophenols and o-Aminothiophenols with Benzylamines. Helvetica Chimica Acta, 93(5).
DOI: 10.1002/hlca.200900350