88847-88-5

Usage

Uses

Used in Pharmaceutical and Analytical Chemistry:
4-Chloroestradiol is utilized as a reference compound for the determination of estradiol impurities through high-performance liquid chromatography (HPLC). This technique is essential for ensuring the purity and quality of estradiol-based pharmaceutical products, as well as for research purposes in endocrinology and reproductive biology.
Used in Environmental Monitoring:
As a contaminant of emerging concern (CECs), 4-chloroestradiol is monitored in environmental samples to assess the presence and impact of endocrine-disrupting chemicals in various ecosystems. This monitoring is crucial for understanding the potential ecological and public health risks associated with exposure to these compounds.

InChI:InChI=1/C18H23ClO2/c1-18-9-8-11-10-4-6-15(20)17(19)13(10)3-2-12(11)14(18)5-7-16(18)21/h4,6,11-12,14,16,20-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1

Upstream product

• 116382-89-9 4,10β-dichloro-17β-hydroxyestra-1,4-dien-3-one 
• 116382-87-7 2,4,10β-trichloro-17β-hydroxyesra-1,4-dien-3-one 
• 50-28-2 estradiol 

Relevant academic research and scientific papers

Effect of 11β-substituents on the regioselective chlorination of estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone

The reaction of 11β-substituted estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone affords exclusively ortho-substituted monochlorinated products including a major 4-chloro and a minor 2-chloro derivative.In the absence of an 11β-substituent, regioselectivity is lost, resulting in a mixture of 10β- and ortho-chlorinated products.Keywords: estradiol derivative; regioselective chlorination; 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone

10&β-Chloro-17&β-hydroxyestra-1,4-dien-3-one and its Related Compounds

Chlorination of steroidal ring A phenols with N-chloro imide reagents (e.g.N-chlorosuccinimide and trichloroisocyanuric acid) afforded the 10β-chloroestra-1,4-dien-3-one (2) together with a smaller proportion of 2,4,10β-trichloroestra-1,4-dien-3-one (4), 2,10β-, and 4,10β-dichloroestra-1,4-dien-3-one .In contrast with the results of bromination using N-bromo imide reagents, only substitution of aromatic ring A was observed.The structure of compound (2b) was established by an X-ray diffraction study.Compounds (2a) and (2b) were readily reduced to the original phenol, and compound (2a) underwent dienone-phenol rearrangement with acetic anhydride-sulphuric acid to yield 4-chloroestra-1,3,5(10)-triene-1,17-diyl diacetate (7).