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CAS No.: | 84449-90-1 |
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Name: | Raloxifene |
Article Data: | 29 |
Molecular Structure: | |
Formula: | C28H27NO4S |
Molecular Weight: | 473.593 |
Synonyms: | Keoxifene;LY 139481;[2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-(2-(1-piperidinyl)ethoxy)phenyl]methanone; |
EINECS: | 686-786-1 |
Density: | 1.289 g/cm3 |
Melting Point: | 250-253 °C |
Boiling Point: | 728.2 °C at 760 mmHg |
Flash Point: | 394.2 °C |
Solubility: | DMSO: 28 mg/mL, soluble |
Appearance: | light-yellow solid |
PSA: | 98.24000 |
LogP: | 6.01310 |
raloxifene hydrochloride
Raloxifen
Conditions | Yield |
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Stage #1: raloxifene hydrochloride With sodium hydroxide In water; acetone at 20℃; Stage #2: With acetic acid In water; acetone at 16 - 20℃; for 1.75h; pH=8; | 100% |
Stage #1: raloxifene hydrochloride With sodium hydroxide In water; acetone at 20℃; Stage #2: With acetic acid In water; acetone at 16 - 18℃; for 0.75h; pH=8; | 100% |
With sodium hydroxide; water; isopropyl alcohol at 20℃; for 5h; pH=9; | |
With sodium hydroxide In methanol; water at 15 - 30℃; for 12.5h; pH=8 - 8.5; | 180 g |
1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide
Raloxifen
Conditions | Yield |
---|---|
Stage #1: 1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide With sodium hydroxide In water; acetone at 20℃; Stage #2: With acetic acid In water; acetone at 12℃; for 1h; pH=8 - 9; | 100% |
Stage #1: 1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide With sodium hydroxide In 1,4-dioxane; water at 16 - 20℃; Stage #2: With acetic acid In 1,4-dioxane; water for 0.166667h; pH=8; Product distribution / selectivity; | 85.8% |
[6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-Piperidinyl)ethoxy]phenyl] Methanone
Raloxifen
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 50℃; | 90% |
With aluminium trichloride; ethanethiol demethylation; | 78% |
In dichloromethane for 6h; Ionic liquid; Reflux; | 61% |
1-piperidinoethanol
[2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl] [4-fluorophenyl]methanone
Raloxifen
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 5h; | 86% |
<6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothien-3-yl><4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methanone hydrochloride
Raloxifen
Conditions | Yield |
---|---|
Stage #1: <6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothien-3-yl><4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methanone hydrochloride With potassium hydroxide; water In dimethyl sulfoxide at 60 - 62℃; for 4h; Stage #2: With acetic acid In water; dimethyl sulfoxide at 20℃; Stage #3: With ammonia In water; dimethyl sulfoxide at 20℃; Product distribution / selectivity; | 70.5% |
Stage #1: <6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothien-3-yl><4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methanone hydrochloride With potassium hydroxide; water In dimethyl sulfoxide at 60 - 62℃; for 4h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 1h; Stage #3: With ammonia In water; dimethyl sulfoxide at 20℃; Product distribution / selectivity; | 66.33% |
With sodium hydroxide In ethanol for 1.5h; Heating; | 42% |
Raloxifen
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide Inert atmosphere; | 67% |
Stage #1: 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-piperidinoethoxy)-benzoyl]benzo[b]thiophene With sodium hydroxide; ethanol; water for 1.5h; Stage #2: In water Acidic aqueous solution; Stage #3: With sodium hydrogencarbonate In water Product distribution / selectivity; | 42.2% |
With sodium hydroxide In tetrahydrofuran; methanol; chloroform | |
With sodium hydroxide In tetrahydrofuran; methanol; chloroform | |
With sodium hydroxide In tetrahydrofuran; methanol; chloroform |
1-piperidinoethanol
Raloxifen
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / NaH / dimethylformamide / 0.5 h / 20 °C 2: 78 percent / AlCl3; ethanethiol View Scheme | |
Multi-step reaction with 3 steps 1: 97 percent / NaH / dimethylformamide / 0.25 h / 20 °C 2: 90 percent / tetrahydrofuran / 2 h / 5 - 23 °C 3: 78 percent / AlCl3; ethanethiol View Scheme |
4-fluorobenzoyl chloride
Raloxifen
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 70 percent / chlorobenzene / 20 °C 2: 97 percent / NaH / dimethylformamide / 0.25 h / 20 °C 3: 90 percent / tetrahydrofuran / 2 h / 5 - 23 °C 4: 78 percent / AlCl3; ethanethiol View Scheme | |
Multi-step reaction with 4 steps 1: 70 percent / chlorobenzene / 20 °C 2: 83 percent / tetrahydrofuran / 1 h / 5 - 23 °C 3: 90 percent / NaH / dimethylformamide / 0.5 h / 20 °C 4: 78 percent / AlCl3; ethanethiol View Scheme | |
Multi-step reaction with 4 steps 1: 70 percent / chlorobenzene / 20 °C 2: 97 percent / dimethylformamide / 0.25 h / 20 °C 3: 90 percent / tetrahydrofuran / 2 h / 5 - 23 °C 4: 78 percent / AlCl3; ethanethiol View Scheme | |
Multi-step reaction with 3 steps 1: 74 percent / AlCl3 / CH2Cl2 2: 81 percent / BBr3 / CH2Cl2 / 3 h / 5 °C 3: 86 percent / NaH / dimethylformamide / 5 h / 50 °C View Scheme |
6-methoxy-N,N-dimethylbenzo[b]thiophen-2-amine
Raloxifen
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 70 percent / chlorobenzene / 20 °C 2: 97 percent / NaH / dimethylformamide / 0.25 h / 20 °C 3: 90 percent / tetrahydrofuran / 2 h / 5 - 23 °C 4: 78 percent / AlCl3; ethanethiol View Scheme | |
Multi-step reaction with 4 steps 1: 70 percent / chlorobenzene / 20 °C 2: 83 percent / tetrahydrofuran / 1 h / 5 - 23 °C 3: 90 percent / NaH / dimethylformamide / 0.5 h / 20 °C 4: 78 percent / AlCl3; ethanethiol View Scheme | |
Multi-step reaction with 4 steps 1: 70 percent / chlorobenzene / 20 °C 2: 97 percent / dimethylformamide / 0.25 h / 20 °C 3: 90 percent / tetrahydrofuran / 2 h / 5 - 23 °C 4: 78 percent / AlCl3; ethanethiol View Scheme |
[2-dimethylamino-6-methoxybenzothien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone
Raloxifen
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / tetrahydrofuran / 2 h / 5 - 23 °C 2: 78 percent / AlCl3; ethanethiol View Scheme |
Molecular Structure:
Molecular Formula: C28H27NO4S
Molecular Weight: 473.5833
IUPAC Name: [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
Synonyms of Raloxifene (CAS NO.84449-90-1): Raloxifene [INN:BAN] ; (2-(4-Hydroxyphenyl)-6-hydroxybenzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)methanone ; CCRIS 7129 ; HSDB 7460 ; LY 139481 ; Raloxifeno ; Raloxifeno [Spanish] ; Raloxifenum ; Raloxifenum [Latin] ; UNII-YX9162EO3I ; Keoxifene ; Methanone, (6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-
CAS NO: 84449-90-1
Classification Code: Anti-estrogen ; Bone Density Conservation Agents ; Estrogen Receptor Modulators ; Estrogen antagonists ; Hormone Antagonists ; Hormones, Hormone Substitutes, and Hormone Antagonists ; Selective Estrogen Receptor Modulators
Melting point: 250-253°C
Index of Refraction: 1.666
Molar Refractivity: 136.57 cm3
Molar Volume: 367.3 cm3
Surface Tension: 57.3 dyne/cm
Density: 1.289 g/cm3
Flash Point: 394.2 °C
Enthalpy of Vaporization: 110.08 kJ/mol
Boiling Point: 728.2 °C at 760 mmHg
Vapour Pressure: 6.46E-22 mmHg at 25°C
Raloxifene (CAS NO.84449-90-1) is used as a nonsteroidal estrogen receptor mixed agonist/antagonist.
WGK Germany of Raloxifene (CAS NO.84449-90-1): 3