1-(2-Chloroacetyl)-5,9b-difluoro-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl propanoate

Base Information

• Chemical Name: 1-(2-Chloroacetyl)-5,9b-difluoro-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl propanoate
• CAS No.: 66852-54-8
• Molecular Formula: C25H31ClF2O5
• Molecular Weight: 484.968
• Hs Code.: 2937220000
• European Community (EC) Number: 686-247-0
• DSSTox Substance ID: DTXSID40860827
• NCI Thesaurus Code: C47553
• RXCUI: 45318
• Mol file: 66852-54-8.mol

Synonyms:6 alpha-fluoroclobetasol 17-propionate;6-fluoroclobetasol 17-propionate;CGP 14 458;CGP 14458;CGP-14458;halobetasol;halobetasol propionate;ulobetasol;Ultravate

Chemical Property of 1-(2-Chloroacetyl)-5,9b-difluoro-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl propanoate

Chemical Property:

• Appearance/Colour: Distributed as 0.05% ointment.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: -32°C
• Refractive Index: 1.551
• Boiling Point: 570.7 °C at 760 mmHg
• PKA: 12.55±0.70(Predicted)
• Flash Point: 298.9 °C
• PSA: 80.67000
• Density: 1.31 g/cm³
• LogP: 4.05110
• Storage Temp.: Refrigerator
• Solubility.: Dioxane (Sparingly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 484.1828081
• Heavy Atom Count: 33
• Complexity: 964

Purity/Quality:

99% ^*data from raw suppliers

HalobetasolPropionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)OC1(C(CC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)C)C(=O)CCl
• Description: Halobetasol propionate is a new ultra-potent topical corticosteroid exhibiting both antiinflammatory and antihyperplasia properties. The compound is recommended for the treatment of moderate to severe corticosteroid-responsive dermatoses and appears to be particularly effective in patients with plaque psoriasis. Halobetasol propionate is a synthetic glucocorticoid. It inhibits dermatitis induced by ultraviolet light in guinea pigs (ED50 = 1.45 μg/animal) and by oxazolone in mice (ED50 = 0.8 μg/animal). Halobetasol propionate also has anti-inflammatory effects on croton oil-induced ear edema in rats (ED50s = 10 μg/ml and 0.5 μg/ear) and mice (ED50s = 1.2 and <0.32 μg/ear after 6 and 24 hours of treatment, respectively). Topical formulations containing halobetasol propionate have been used for inflammatory and pruritic dermatitis.
• Uses: Anti-inflammatory; a dermatologic agent commonly used to treat psoriasis

Technology Process of 1-(2-Chloroacetyl)-5,9b-difluoro-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl propanoate

There total 4 articles about 1-(2-Chloroacetyl)-5,9b-difluoro-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl propanoate 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:

6α,9α-difluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, 17-propionate 21-mesylate (84509-92-2) → halobetasol propionate (66852-54-8) + halobetasol (98651-66-2) + 6α,9α-difluoro-11β-hydroxy-16β-methyl-3-oxoandrosta-1,4-diene-17(R)-spiro-2'-[4'-chloro-5'-ethylfuran-3-(2'H)-one] + 6α,9α-difluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, 21-propionate (541502-98-1) + 6α,9α-difluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, 17-propionate (924726-89-6) + 11β,17α,21-trihydroxy-6α,9α-difluoro-16β-methylpregna-1,4-diene-3,20-dione (2557-49-5)

Guidance literature:

6α,9α-difluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, 17-propionate 21-mesylate; With lithium chloride; In ISOPROPYLAMIDE; at 80 ℃; for 3h;

With water; In ISOPROPYLAMIDE; at 20 ℃; for 1.83333h;

Reference yield:

halobetasol propionate methylene chloride → halobetasol propionate (66852-54-8)

Guidance literature:

at 140 ℃; for 0.166667h;

Reference yield:

halobetasol propionate ethyl acetate → halobetasol propionate (66852-54-8)

Guidance literature:

at 120 ℃; for 0.166667h;

upstream raw materials:

6α,9α-difluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione, 17-propionate 21-mesylate

Refernces

• 1、 -. "Crystalline forms of halobetasol propionate". Page 6. . Retrieved 2008/06/13.
• 2、 -. "Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor". . . Retrieved 2008/06/13.