549-03-1

Basic information

• Product Name: 10-hydroxyestra-1,4-diene-3,17-dione
• CAS NO: 549-03-1
• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.3655
• Mol File: 549-03-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 485.2°C at 760 mmHg
• Flash Point: 261.3°C
• Density: 1.24g/cm³
• Vapor Pressure: 1.89E-11mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: 10-hydroxyestra-1,4-diene-3,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 10-hydroxyestra-1,4-diene-3,17-dione(549-03-1)
• EPA Substance Registry System: 10-hydroxyestra-1,4-diene-3,17-dione(549-03-1)

Safety Data

• Hazardous Substances Data: 549-03-1(Hazardous Substances Data)

Upstream product

• 86846-54-0 10β-hydroperoxy-estra-1(2),4(5)-dien-3,17-dione 
• 901-93-9 estrone acetate 
• 901-93-9 Oestron-3-acetat 

Downstream Products

• 2208-12-0 6-dehydroestrone 
• 53-16-7 Estrone 
• 4147-12-0 10β-acetoxyestra-1,4-dien-3,17-dione 
• 4147-06-2 1,4-diacetoxyestra-1,3,5(10)-trien-17-one 

Relevant articles and documents

Electrophilic hydroxylation of aromatics in superacids

In superacids, protonated hydrogen peroxide hydroxylates various aromatics to give phenols.The substrates react in their protonated forms with the electrophile H3O2+.Phenols (and their methyl ethers), anilines, indolines, indoles, aromatic aldehydes and ketones are hydroxylated without any degradation; protonation protects the functional group(s) that are normally sensitive to oxidants.Electrophilic hydroxylation of polyfunctional natural products (vincadifformine, estrane derivatives) has been succesfully performed with H2O2/HF/SbF5. - Keywords: superacids / hydroxylation / hydrogen peroxide / aromatics / phenols / indoles

HYDROXYLATION DE L'ESTRONE ET DE SON ACETATE PAR LE PEROXYDE D'HYDROGENE EN MILIEU SUPERACIDE

Estrone 1a and its acetate 1b react with hydrogen peroxide in SbF5-HF to give hydroxylated compounds.The formation of the dienone 2 can be accounted for by reaction of the electrophile H3O2+ on the neutral substrate, whereas formation of compound 3b implies electrophilic attack on the protonated ester 1b.Higher acidity favours rearrangement of the resulting ion 9 to yield, through a spiro intermediate, the ester 4b.Under the reaction conditions esters 3b and 4b are slowly converted into the corresponding phenols 3a and 4a.