2,3-Dichlorobenzyl Bromide: Properties, Uses & Handling FAQ

2,3-Dichlorobenzyl Bromide is a halogenated benzyl reagent widely employed in organic synthesis as an electrophilic alkylating agent for introducing the 2,3-dichlorobenzyl group onto nucleophilic substrates.

Chemical Name

2,3-Dichlorobenzyl Bromide

SKU

D139027

Molecular Formula

C7H5BrCl2

Functional Class

Benzylic alkylating agent / electrophilic halide

Key Reactive Site

Benzylic C–Br bond, highly electrophilic

Typical Storage

Cool, dry, well-ventilated area; away from moisture and light

Chemical Identity and Properties

2,3-Dichlorobenzyl Bromide (SKU: D139027) is an aryl-substituted benzyl bromide bearing two chlorine substituents at the 2- and 3-positions of the phenyl ring. The compound belongs to the class of benzylic halides, characterized by a methylene (–CH₂–) bridge between the aromatic ring and the bromine leaving group. This structural arrangement confers high electrophilicity at the benzylic carbon, making the C–Br bond particularly reactive toward nucleophiles via S_N2 or, under certain conditions, S_N1 mechanisms. The two ortho/meta chlorine substituents exert an electron-withdrawing inductive effect on the ring, which can influence reaction kinetics and the regioselectivity of downstream transformations. The compound is typically encountered as a pale to off-white solid or low-melting crystalline material and is sensitive to moisture, which can promote hydrolysis of the benzylic bromide.

Research Applications and Synthetic Utility

2,3-Dichlorobenzyl Bromide serves as a versatile building block and protecting-group reagent in medicinal chemistry, agrochemical research, and fine-chemical synthesis. Its primary role is as an electrophilic benzylation agent: it reacts readily with oxygen nucleophiles (alcohols, phenols, carboxylates) to form the corresponding 2,3-dichlorobenzyl ethers or esters, and with nitrogen or sulfur nucleophiles to form N- or S-benzylated products. The 2,3-dichlorobenzyl moiety introduced by this reagent can serve as a masked functional handle that is cleaved under specific conditions. Researchers also employ such dichlorobenzyl bromides in the synthesis of pharmaceutically relevant scaffolds, where the halogenated aryl group contributes to lipophilicity and can engage in further cross-coupling reactions (e.g., Suzuki, Negishi) if required. The compound may additionally function as a precursor to 2,3-dichlorobenzyl phosphonium salts or organometallic intermediates.

Safe Handling, Storage, and Stability

As a benzylic bromide, 2,3-Dichlorobenzyl Bromide is a lachrymatory and potentially irritating compound. It should be handled exclusively in a well-ventilated fume hood with appropriate personal protective equipment including chemical-splash goggles, nitrile gloves, and a laboratory coat. Avoid inhalation of vapors or dust and prevent contact with skin, eyes, and mucous membranes. The compound is moisture-sensitive: exposure to atmospheric water can hydrolyze the benzylic bromide to yield the corresponding benzyl alcohol and hydrobromic acid. For storage, keep the reagent tightly sealed in a cool (2–8 °C recommended), dry, dark environment and under inert-gas atmosphere where possible. Incompatibilities include strong bases, strong oxidizers, and nucleophilic solvents such as water or alcohols unless used intentionally as reaction partners. Consult the product Safety Data Sheet (SDS) for full hazard classifications, first-aid measures, and disposal instructions before use.

Ordering, Purity, and Quality Specifications

2,3-Dichlorobenzyl Bromide is available from Aladdin Scientific under SKU D139027. Customers should consult the current product page or contact Aladdin's technical support for up-to-date information on available pack sizes, purity grades, and lot-specific certificates of analysis (CoA). Typical purity specifications for research-grade benzylic bromide reagents are confirmed by GC or HPLC analysis; the CoA will document purity, appearance, and any additional characterization data. For procurement inquiries, volume pricing, or custom quantities, contact the Aladdin sales team. When placing an order, ensure that appropriate import, transport, and hazardous-material regulations applicable to halogenated organic compounds in your jurisdiction are observed, as this compound may be subject to specific shipping restrictions.

Frequently asked questions

What is 2,3-Dichlorobenzyl Bromide used for in organic synthesis?

2,3-Dichlorobenzyl Bromide is primarily used as an electrophilic benzylation reagent. It introduces the 2,3-dichlorobenzyl group onto nucleophilic substrates such as alcohols, phenols, amines, and thiols, producing the corresponding ethers, esters, or N/S-benzylated derivatives. It is also used as a building block in medicinal chemistry and agrochemical synthesis.

How should 2,3-Dichlorobenzyl Bromide be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool (2–8 °C), dry, and dark location, preferably under an inert atmosphere such as nitrogen or argon. Because the benzylic C–Br bond is susceptible to hydrolysis, exposure to moisture must be avoided. Always reseal the container promptly after use.

What safety precautions are required when handling 2,3-Dichlorobenzyl Bromide?

Handle this reagent exclusively in a well-ventilated fume hood. Wear chemical-splash goggles, nitrile gloves, and a laboratory coat at all times. The compound is lachrymatory and may cause skin and respiratory irritation. Consult the product SDS for full hazard information, emergency procedures, and compliant disposal methods before beginning any experiment.

What nucleophiles react well with 2,3-Dichlorobenzyl Bromide?

Common nucleophiles that react efficiently with 2,3-Dichlorobenzyl Bromide include alkoxides and phenoxides (giving benzyl ethers), carboxylates (giving benzyl esters), primary and secondary amines (giving N-benzyl amines), and thiols or thiolates (giving thioethers). The highly electrophilic benzylic carbon undergoes facile SN2 reactions with these species under mild conditions.

Can 2,3-Dichlorobenzyl Bromide participate in cross-coupling reactions?

The two aryl chlorine substituents on 2,3-Dichlorobenzyl Bromide can, in principle, participate in transition-metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura or Negishi coupling, though aryl chlorides generally require more active catalysts than aryl bromides or iodides. Researchers should optimize catalyst system and conditions for specific coupling applications involving this substrate.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for SN2 reactions of benzylic halides.)
2. Aladdin Scientific product page for 2,3-Dichlorobenzyl Bromide, SKU D139027. (Primary source for product identity and availability.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.