The compound's defining feature is its (Z)-configured tetrasubstituted alkene, which must be precisely controlled during synthesis to ensure the correct geometric isomer carries through to the final drug substance --- geometric isomer purity is pharmacologically critical, since the (Z)- and (E)-isomers of triphenylethylene SERMs display markedly different estrogen receptor binding profiles (tamoxifen is the Z-isomer; the E-isomer is a distinct, less desirable compound). The terminal chloroethyl group serves as the electrophilic handle for the subsequent amination step that installs the dimethylaminoethoxy side chain defining tamoxifen's final structure.
(Z)-1-[4-(2-Chloroethoxy)phenyl]-1,2-diphenylbut-1-ene, commonly known as "(Z)-Chlorolefin," is a stereodefined triarylbutene bearing a reactive chloroethoxy side chain. It is a critical late-stage intermediate in the industrial synthesis of tamoxifen and related triphenylethylene-based selective estrogen receptor modulators (SERMs) used in breast cancer therapy.
| Chemical Name | (Z)-1-[4-(2-Chloroethoxy)phenyl]-1,2-diphenylbut-1-ene ((Z)-Chlorolefin) |
| CAS Number | 97818-83-2 |
| IUPAC Name | (Z)-Chlorolefin |
| Molecular Formula | C24H23ClO |
| Molecular Weight | 362.90 g/mol g/mol |
Direct penultimate synthetic intermediate for tamoxifen, a first-line SERM used in hormone receptor-positive breast cancer treatment and prevention.
Building block for structurally related triphenylethylene SERM analogs and research compounds.
Used in API process development to establish stereoselective synthesis routes ensuring Z-isomer geometric purity.
Supports HPLC/chiral method development for monitoring geometric isomer purity in tamoxifen manufacturing.
Br. J. Pharmacol.
J. Chem. Soc. Perkin Trans. 1
J. Med. Chem.
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