17-Bromoacetoxy-4-androsten-3-one

Base Information

• Chemical Name: 17-Bromoacetoxy-4-androsten-3-one
• CAS No.: 4588-81-2
• Molecular Formula: C21H29BrO3
• Molecular Weight: 409.363
• DSSTox Substance ID: DTXSID50963454
• Mol file: 4588-81-2.mol

Synonyms:17-BAAO;17-bromoacetoxy-4-androsten-3-one

Chemical Property of 17-Bromoacetoxy-4-androsten-3-one

Chemical Property:

• Vapor Pressure: 1.2E-09mmHg at 25°C
• Boiling Point: 487.3°Cat760mmHg
• Flash Point: 248.5°C
• PSA: 43.37000
• Density: 1.32g/cm³
• LogP: 4.82500
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 408.13001
• Heavy Atom Count: 25
• Complexity: 627

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2OC(=O)CBr)CCC4=CC(=O)CCC34C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2OC(=O)CBr)CCC4=CC(=O)CC[C@]34C

Technology Process of 17-Bromoacetoxy-4-androsten-3-one

There total 2 articles about 17-Bromoacetoxy-4-androsten-3-one 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: 89.0%

2-bromoacetyl chloride (22118-09-8) + testosterone (58-22-0) → 17β-bromoacetoxy-4-androsten-3-one (4588-81-2)

Guidance literature:

With N,N-dimethyl-aniline; In 1,4-dioxane; at 0 ℃; for 2h;

DOI:10.1016/0039-128X(90)90072-J

Reference yield: 71.0%

testosterone (58-22-0) + 2-Bromoacetyl bromide (598-21-0) → 17β-bromoacetoxy-4-androsten-3-one (4588-81-2)

Guidance literature:

With N,N-dimethyl-aniline; In 1,4-dioxane; at 0 ℃; for 3h;

DOI:10.1002/adsc.202001209

Reference yield:

17β-bromoacetoxy-4-androsten-3-one (4588-81-2) → testosterone 17β-phenylpropionate (1255-49-8)

Guidance literature:

Multi-step reaction with 3 steps

1: benzene / 24 h

2: sodium hydroxide / water; methanol / 3 h

3: potassium tert-butylate; C₁₆H₃₅BrMnN₃O₂P₂ / 1,4-dioxane / 24 h / 130 °C / Inert atmosphere

With potassium tert-butylate; C₁₆H₃₅BrMnN₃O₂P₂; sodium hydroxide; In 1,4-dioxane; methanol; water; benzene;

DOI:10.1002/adsc.202001209

upstream raw materials:

2-bromoacetyl chloride

testosterone

2-Bromoacetyl bromide

Downstream raw materials:

testosterone triphenylphosphoranylideneacetate

testosterone 17β-phenylpropionate

Refernces

• 1、 -. "Testosterone prodrugs for improved drug delivery". . . Retrieved 2008/06/13.
• 2、 -. "Brain-specific drug delivery". . . Retrieved 2008/06/13.