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Raloxifene
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Name

Raloxifene

 EINECS 686-786-1
CAS No. 84449-90-1 Density 1.289 g/cm3
PSA 98.24000 LogP 6.01310
Solubility DMSO: 28 mg/mL, soluble Melting Point 250-253 °C
Formula C28H27NO4S Boiling Point 728.2 °C at 760 mmHg
Molecular Weight 473.593 Flash Point 394.2 °C
Transport Information N/A Appearance light-yellow solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 84449-90-1 (Raloxifene) Hazard Symbols N/A
Synonyms

Keoxifene;LY 139481;[2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-(2-(1-piperidinyl)ethoxy)phenyl]methanone;

Article Data 29

Raloxifene Synthetic route

82640-04-8

raloxifene hydrochloride

84449-90-1

Raloxifen

Conditions
ConditionsYield
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
1293408-87-3

1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide

84449-90-1

Raloxifen

Conditions
ConditionsYield
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%
84541-38-8

[6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-Piperidinyl)ethoxy]phenyl] Methanone

84449-90-1

Raloxifen

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 50℃;90%
With aluminium trichloride; ethanethiol demethylation;78%
In dichloromethane for 6h; Ionic liquid; Reflux;61%
3040-44-6

1-piperidinoethanol

202336-25-2

[2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl] [4-fluorophenyl]methanone

84449-90-1

Raloxifen

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 5h;86%
84449-85-4

<6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothien-3-yl><4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methanone hydrochloride

84449-90-1

Raloxifen

Conditions
ConditionsYield
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%

6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-piperidinoethoxy)-benzoyl]benzo[b]thiophene

84449-90-1

Raloxifen

Conditions
ConditionsYield
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
3040-44-6

1-piperidinoethanol

84449-90-1

Raloxifen

Conditions
ConditionsYield
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
403-43-0

4-fluorobenzoyl chloride

84449-90-1

Raloxifen

Conditions
ConditionsYield
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
111359-29-6

6-methoxy-N,N-dimethylbenzo[b]thiophen-2-amine

84449-90-1

Raloxifen

Conditions
ConditionsYield
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
165742-76-7

[2-dimethylamino-6-methoxybenzothien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone

84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / tetrahydrofuran / 2 h / 5 - 23 °C
2: 78 percent / AlCl3; ethanethiol
View Scheme

Raloxifene Chemical Properties

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 Uses

  Raloxifene (CAS NO.84449-90-1) is used as a nonsteroidal estrogen receptor mixed agonist/antagonist.

Raloxifene Safety Profile

WGK Germany of Raloxifene (CAS NO.84449-90-1): 3

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