4-Nitroestrone

Base Information

• Chemical Name: 4-Nitroestrone
• CAS No.: 5976-74-9
• Molecular Formula: C18H21 N O4
• Molecular Weight: 315.369
• NSC Number: 239728,32058
• UNII: IM60NNH5BH
• DSSTox Substance ID: DTXSID90975172
• Nikkaji Number: J456.532K
• Wikidata: Q27149003
• ChEMBL ID: CHEMBL1835541
• Mol file: 5976-74-9.mol

Synonyms:4-Nitroestrone;IM60NNH5BH;3-Hydroxy-4-nitroestra-1,3,5(10)-trien-17-one;NSC-32058;NSC-239728;5976-74-9;UNII-IM60NNH5BH;CHEMBL1835541;CHEBI:79864;1,3,5(10)-Estratrien-4-nitro-3-ol-17-one;Estra-1,3,5(10)-trien-17-one, 3-hydroxy-4-nitro-;MLS003115201;SCHEMBL670939;DTXSID90975172;WNYWRAYXFFPPGN-QDTBLXIISA-N;NSC32058;BDBM50355361;NSC239728;Q27149003

Chemical Property of 4-Nitroestrone

Chemical Property:

• Vapor Pressure: 3.41E-09mmHg at 25°C
• Boiling Point: 463°Cat760mmHg
• Flash Point: 187.4°C
• Density: 1.292g/cm³
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 315.14705815
• Heavy Atom Count: 23
• Complexity: 530

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4[N+](=O)[O-])O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4[N+](=O)[O-])O

Technology Process of 4-Nitroestrone

There total 9 articles about 4-Nitroestrone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

Estrone (53-16-7) → 2-nitroestrone (5976-73-8) + 4-nitroestrone (5976-74-9)

Guidance literature:

With Phenylselenyl chloride; silver nitrate; In acetonitrile; for 3h; Ambient temperature;

Reference yield: 45.0%

Estrone (53-16-7) → 4-nitroestrone (5976-74-9)

Guidance literature:

With nitric acid; In dichloromethane; at 40 ℃; for 1h;

DOI:10.1039/d1ra01889b

Reference yield: 13.0%

Estrone (53-16-7) + phenobarbital (50-06-6) → 4-nitroestrone (5976-74-9)

Guidance literature:

With nitric acid; In acetic acid;

upstream raw materials:

Estrone

phenobarbital

2-nitroestrone

Downstream raw materials:

4-nitroestrone 3-O-(3-hydroxypropyl) ether

4-aminoestra-1,3,5(10)-triene-3,17β-diol

4-nitro-3-benzyloxyestra-1,3,5-triene-17-one

(5bS,7aS,10aS,10bR)-2-(4-Methoxy-phenylamino)-7a-methyl-5b,6,7,7a,9,10,10a,10b,11,12-decahydro-3-oxa-1-aza-dicyclopenta[a,i]phenathren-8-one

Refernces

• 1、 Kovács, Ferenc,Gopisetty, Mohana K.,Adamecz, Dóra I.,Kiricsi, Mónika,Enyedy, éva A.,Frank, éva. "Synthesis and conversion of primary and secondary 2-aminoestradiols into A-ring-integrated benzoxazolone hybrids and theirin vitroanticancer activity". . p. 13885 - 13896. Retrieved 2021/04/22.
• 2、 Mostafa, Yaser A.,Kralt, Braden,Rao, Praveen P.N.,Taylor, Scott D.. "A-ring substituted 17β-arylsulfonamides of 17β-aminoestra-1,3,5(10)-trien-3-ol as highly potent reversible inhibitors of steroid sulfatase". . p. 5681 - 5692. Retrieved 2015/11/11.