2,3-Difluoro-6-methoxybenzyl Chloride
[CAS# 1073435-67-2]

Identification

• Classification: Organic raw materials >> Organic fluorine compound
• Name: 2,3-Difluoro-6-methoxybenzyl Chloride
• Synonyms: 3-(chloromethyl)-1,2-difluoro-4-methoxybenzene
• Molecular Formula: C₈H₇ClF₂O
• Molecular Weight: 192.59
• CAS Registry Number: 1073435-67-2
• EC Number: 971-704-1
• SMILES: COC1=C(C(=C(C=C1)F)F)CCl

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314-H335
• Safety Statements: P260-P261-P264-P270-P271-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P319-P321-P330-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2,3-Difluoro-6-methoxybenzyl chloride is an organofluorine compound known for its significant role as an intermediate in organic synthesis. Structurally, it consists of a benzene ring substituted with two fluorine atoms at the 2 and 3 positions, a methoxy group at the 6 position, and a benzyl chloride moiety. This unique substitution pattern endows it with specific reactivity, making it a valuable building block for more complex molecules.

The discovery of 2,3-difluoro-6-methoxybenzyl chloride can be traced back to studies on the functionalization of aromatic rings through electrophilic substitution. Fluorinated aromatics gained prominence due to the growing interest in pharmaceuticals and agrochemicals, where the presence of fluorine atoms can enhance biological activity and metabolic stability. The incorporation of a methoxy group further modulates the electronic properties of the ring, influencing the reactivity of the molecule.

The most common synthesis method for 2,3-difluoro-6-methoxybenzyl chloride involves the chloromethylation of 2,3-difluoro-6-methoxytoluene. This reaction typically employs formaldehyde and hydrochloric acid in the presence of a Lewis acid catalyst such as zinc chloride. The process requires careful control of reaction conditions to ensure selective chloromethylation while minimizing side reactions. After chloromethylation, the benzyl chloride derivative is purified by standard techniques such as distillation or crystallization.

In terms of application, 2,3-difluoro-6-methoxybenzyl chloride serves as a crucial intermediate in the synthesis of pharmaceutical agents, particularly those targeting neurological or cardiovascular conditions. Its fluorine atoms enhance the bioavailability and receptor-binding affinity of the final compounds. Additionally, this molecule is used in agrochemical development, where fluorinated benzyl derivatives improve the efficacy and persistence of pesticides and herbicides. The versatility of this compound lies in its ability to undergo further functionalization, including nucleophilic substitution or coupling reactions, facilitating the construction of complex molecular scaffolds.

Research continues to explore novel derivatives of 2,3-difluoro-6-methoxybenzyl chloride for potential applications in medicinal chemistry and materials science. Its importance as a synthetic intermediate underscores the ongoing demand for precision fluorination techniques in modern chemical synthesis.


References

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