19590-55-7

Basic information

• Product Name: 2,4-DIBROMOESTRADIOL
• Synonyms: 2,4-Dibromoestradiol(formB);2,4-DIBROMOESTRADIOL;1,3,5(10)-ESTRATRIEN-2,4-DIBROMO-3,17-BETA-DIOL;2,4-dibromo-17-estradiol
• CAS NO: 19590-55-7
• Molecular Formula: C₁₈H₂₂Br₂O₂
• Molecular Weight: 430.17
• Mol File: 19590-55-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 454.8°Cat760mmHg
• Flash Point: 228.9°C
• Appearance: /
• Density: 1.623g/cm³
• Vapor Pressure: 4.61E-09mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 2,4-DIBROMOESTRADIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIBROMOESTRADIOL(19590-55-7)
• EPA Substance Registry System: 2,4-DIBROMOESTRADIOL(19590-55-7)

Safety Data

• Hazardous Substances Data: 19590-55-7(Hazardous Substances Data)

Usage

General Description

2,4-DIBROMOESTRADIOL is a synthetic derivative of the hormone estradiol, which is a form of estrogen. It is a potent inhibitor of cytochrome P450 enzymes, which play a crucial role in the metabolism of various drugs and hormones in the body. 2,4-DIBROMOESTRADIOL has been studied for its potential anti-cancer effects, particularly in hormone-sensitive tumors such as breast cancer. It has been shown to inhibit the growth of breast cancer cells in laboratory studies, and may have potential as a therapeutic agent for certain types of cancer. However, further research is needed to fully understand its mechanisms of action and potential therapeutic applications.

InChI:InChI=1/C18H22Br2O2/c1-18-7-6-9-10(13(18)4-5-15(18)21)2-3-11-12(9)8-14(19)17(22)16(11)20/h8-10,13,15,21-22H,2-7H2,1H3

Upstream product

• 15087-02-2 estradiol-17β 17-(β-D-glucuronide) sodium salt 
• 50-28-2 estradiol 
• 79-15-2 N-bromoacetamide 
• 64-17-5 ethanol 

Downstream Products

• 15087-02-2 estradiol-17β 17-(β-D-glucuronide) sodium salt 
• 549-02-0 10β,17β-dihydroxyestra-1,4-dien-3-one 
• 6301-87-7 2-Aminoestratriene-3,17beta-diol 
• 362-05-0 2-Hydroxyestradiol 
• 26788-23-8 4-methoxy-17β-estradiol 
• 15833-07-5 2-bromoestradiol 
• 434-22-0 19-nortestosterone 
• 50-28-2 estradiol 
• 1630-83-7 4-bromo-β-estradiol 

Relevant articles and documents

A NEW SYNTHETIC ROUTE TO PYROGALLOLESTROGEN DIMETHYL ETHERS BY NUCLEOPHILIC SUBSTITUTION OF 2,4-DIBROMOESTROGENS

A novel synthetic route to pyrogallolestrogen dimethyl ethers was developed.Benzo-15-crown-5 with CuI catalyses the specific nucleophilic substitution of bromo atoms by methoxide ions.

Chemical synthesis of two novel diaryl ether dimers of estradiol-17β

We recently detected the formation of estradiol-17β (estradiol) dimers, linked together through a diaryl ether bond between the C-3 phenolic oxygen of one estradiol molecule and the 2- or 4-position aromatic carbon of another estradiol, following incubations of [3H]estradiol with human liver microsomes or cytochrome P450 enzymes in the presence of NADPH. Using estradiol as the starting material, we designed a four-step method for the chemical synthesis of these two estrogen dimers with the Ullmann condensation reaction as a key step. Step 1: Synthesis of 2- or 4-bromoestradiol from estradiol. Step 2: Protection of the C-3 phenolic hydroxyl group of the 2- or 4-bromoestradiol. Step 3: The Ullmann condensation reaction between the phenol-protected bromoestradiol and the estradiol potassium salt under our modified reaction conditions (with a 41% product yield). Step 4: Removal of the C-3 benzyl group by catalytic hydrogenation. The chromatographic and various spectrometric properties of the two synthesized compounds were identical to those metabolically formed by human cytochrome P450 3A4.

Reaction of Benzeneselenyl Halides with Estrogens

The reaction of estradiol and estrone with benzeneselenyl chloride affords mainly 2-phenylselenyl adducts which are readily converted into the corresponding 2-halogenated estrogens upon treatment with a variety of reagents.