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2135-17-3

Basic Information
CAS No.: 2135-17-3
Name: Flumethasone
Molecular Structure:
Molecular Structure of 2135-17-3 (Flumethasone)
Formula: C22H28F2O5
Molecular Weight: 410.458
Synonyms: U-10,974;Anaprime;Prestwick_229;Pregna-1,4-diene-3,20-dione, 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxy-16.alpha.-methyl-;Flucorticin;6alpha,9alpha-Difluoro-16alpha-methylprednisolone;U-10974;Fluvet;Cortexillar;RS 2177;Flumethason;Flucort (Veterinary);6alpha-Fluorodexamethasone;Testosterone Undecanoate;
EINECS: 218-370-9
Density: 1.36 g/cm3
Melting Point: 237-240oC
Boiling Point: 569.8 °C at 760 mmHg
Flash Point: 298.4 °C
Solubility: 1mg/L(20 oC)
Appearance: White crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 40
Safety: 22-36
PSA: 94.83000
LogP: 1.84370
Synthetic route

C24H30F2O5

2135-17-3

flumetasone

Conditions
ConditionsYield
With monoperoxyphthalic acid In dichloromethane; ethyl acetate at 27℃;93%
2002-29-1

flumethasone pivalate

2135-17-3

flumetasone

Conditions
ConditionsYield
With Curvularia lunata In water at 30℃; for 72h; Yield given;

4,6 alpha,9 alpha-trifluoro-11 beta,17 alpha-dihydroxy-16 alpha-methyl-3-oxoandrosta-1,4-diene

A

4,6 alpha,9 alpha-trifluoro-11 beta-hydroxy-16 alpha-methyl-3-oxo-17 alpha-propionyloxyandrosta-1,4-diene

B

2135-17-3

flumetasone

Conditions
ConditionsYield
With pyridine In propionic acid anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; water / methanol / 10 h
2: hydrogen fluoride / 5 h / -15 - -10 °C
View Scheme
epoxyparamethasone

epoxyparamethasone

2135-17-3

flumetasone

Conditions
ConditionsYield
With hydrogen fluoride at -15 - -10℃; for 5h;
2135-17-3

flumetasone

28416-82-2

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid

Conditions
ConditionsYield
With water; periodic acid In tetrahydrofuran at 20℃; for 1h;100%
With periodic acid In tetrahydrofuran; water at 0 - 20℃; for 2h;99.12%
With periodic acid In tetrahydrofuran; water at 0 - 20℃; for 5.75h;98%
34914-36-8

2-(triphenylmethylthio)ethanoic acid

2135-17-3

flumetasone

flumethasone 2-(tritylmercapto)acetate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃;98%
2135-17-3

flumetasone

C22H27BrF2O4

Conditions
ConditionsYield
With pyridine; N-Bromosuccinimide; sulfur dioxide at 20℃; for 1h;97.3%
2135-17-3

flumetasone

2607-06-9

6α,9-difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With trimethylsilyl iodide In acetonitrile at -20℃; for 2h; Inert atmosphere;93%
2135-17-3

flumetasone

115-80-0

Triethyl orthopropionate

22593-09-5

6α,9α-difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione cyclic 17,21-(ethyl orthopropionate)

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; toluene at 20℃; for 2h;90%
Downstream Products
2607-06-9
28416-82-2
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Specification

1. Introduction of Flumethasone
Flumethasone is an odorless, white to creamy white, crystalline pow­der. The IUPAC name is (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one.

2. Properties of Flumethasone
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 5
Polar Surface Area: 61.83 Å2
Index of Refraction: 1.579
Molar Refractivity: 100.33 cm3
Molar Volume: 301.7 cm3
Surface Tension: 54.3 dyne/cm
Density: 1.36 g/cm3
Flash Point: 298.4 °C
Enthalpy of Vaporization: 98.19 kJ/mol
Boiling Point: 569.8 °C at 760 mmHg
Vapour Pressure: 2.33E-15 mmHg at 25°C
Storage temp.: 2-8°C

3. Structure Descriptors of Flumethasone
SMILES: O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)[C@@H](F)C[C@H]4[C@@H]2C[C@H]3C)C)C
InChI: InChI=1/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1 Copy
InChIKey: WXURHACBFYSXBI-GQKYHHCABT
Std. InChI: InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
Std. InChIKey: WXURHACBFYSXBI-GQKYHHCASA-N

4. Safety Information of Flumethasone

Hazard Codes: HarmfulXn
Risk Statements: 40
40: Limited evidence of a carcinogenic effect
Safety Statements: 22-36
22: Do not breathe dust
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: TU3832000
Experimental reproductive effects. When heated to decomposition it emits toxic fumes of F.

5. Use of Flumethasone
Flumethasone is a glucocorticoid. It is an anti-inflammatory and a corticosteroid for topical use. Besides, flumethasone is also used for the treatment of otitis externa and otomycosis.