This ketone intermediate sits early in the tamoxifen synthetic pathway, positioned before the alkene-forming step. Its carbonyl group undergoes downstream transformation --- typically via Grignard addition and dehydration --- to construct the tetrasubstituted (Z)-configured alkene characteristic of tamoxifen and related SERMs (such as the "(Z)-Chlorolefin" intermediate). The terminal chloroethyl group is preserved through this sequence, ultimately serving as the electrophilic site for the final amination step that installs the dimethylaminoethoxy side chain in tamoxifen.
1-[4-(2-Chloroethoxy)phenyl]-2-phenylbutan-1-one is an aryl ketone bearing a reactive chloroethoxy substituent, serving as a key upstream intermediate in the industrial synthesis of tamoxifen and its metabolites, including afimoxifene (4-hydroxytamoxifen) and related triphenylethylene selective estrogen receptor modulators (SERMs).
| Chemical Name | 1-[4-(2-Chloroethoxy)phenyl]-2-phenylbutan-1-one |
| CAS Number | 103628-22-4 |
| IUPAC Name | 1-[4-(2-Chloroethoxy)phenyl]-2-phenylbutan-1-one |
| Molecular Formula | C18H19ClO2 |
| Molecular Weight | 302.80 g/mol g/mol |
| Boiling Point | 445.3°C at 760 mmHg |
| Density | 1.132 g/cm³ |
Upstream synthetic intermediate in the multi-step industrial route to tamoxifen citrate.
Building block for producing afimoxifene (4-hydroxytamoxifen) and related active metabolite reference standards.
Used in API process optimization studies for establishing efficient, scalable tamoxifen synthesis routes.
Supports early-stage process impurity characterization and synthetic route validation.
Br. J. Pharmacol.
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