The terminal alkyl chloride of this molecule readily undergoes nucleophilic substitution reactions (Friedel-Crafts acylation, Williamson ether synthesis, and amine displacement), making it a workhorse intermediate for installing chloroethoxyphenyl and dimethylaminoethoxyphenyl motifs common across multiple drug classes. Its role in tamoxifen-related synthesis specifically involves Friedel-Crafts acylation to construct the chloroethoxyphenyl ketone precursor, which is subsequently elaborated into the full triphenylethylene SERM scaffold.
2-(2-Chloroethoxy)benzene, also known as 2-phenoxyethyl chloride or ß-chlorophenetole, is a versatile alkylating agent combining a phenyl ether linkage with a terminal reactive chloride. It serves as a foundational building block across pharmaceutical API synthesis, most notably in routes toward tamoxifen-class SERMs and various chloroethoxyphenyl-substituted drug intermediates.
| Chemical Name | 2-(2-Chloroethoxy)benzene (2-Phenoxyethyl Chloride, ß-Chlorophenetole) |
| CAS Number | 622-86-6 |
| IUPAC Name | 2-Chloroethoxybenzene |
| Molecular Formula | C8H9ClO |
| Molecular Weight | 156.61 g/mol g/mol |
Key building block for constructing chloroethoxyphenyl ketone precursors in triphenylethylene SERM manufacturing.
Widely used reagent for installing chloroethoxy or (after amination) aminoethoxy side chains across various API structures.
Related structurally to intermediates used in chlorpheniramine and similar antihistamine synthesis routes.
General-purpose building block for medicinal chemistry and CDMO process development.
Br. J. Pharmacol.
Advanced Organic Chemistry (reference text)
J. Chem. Soc. Perkin Trans. 1
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