Product Name

  • Name

    Raloxifene

  • EINECS 686-786-1
  • CAS No. 84449-90-1
  • Article Data29
  • CAS DataBase
  • Density 1.289 g/cm3
  • 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
  • Appearance light-yellow solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 84449-90-1 (Raloxifene)
  • Hazard Symbols
  • Synonyms Keoxifene;LY 139481;[2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-(2-(1-piperidinyl)ethoxy)phenyl]methanone;
  • PSA 98.24000
  • LogP 6.01310

Synthetic route

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Raloxifen
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
1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide
1293408-87-3

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

Raloxifen
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%
[6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-Piperidinyl)ethoxy]phenyl] Methanone
84541-38-8

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

Raloxifen
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%
1-piperidinoethanol
3040-44-6

1-piperidinoethanol

[2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl] [4-fluorophenyl]methanone
202336-25-2

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

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
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
84449-85-4

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

Raloxifen
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

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

Raloxifen
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
1-piperidinoethanol
3040-44-6

1-piperidinoethanol

Raloxifen
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
4-fluorobenzoyl chloride
403-43-0

4-fluorobenzoyl chloride

Raloxifen
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
6-methoxy-N,N-dimethylbenzo[b]thiophen-2-amine
111359-29-6

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

Raloxifen
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
[2-dimethylamino-6-methoxybenzothien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone
165742-76-7

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

Raloxifen
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
6-methoxy-2-(4-methoxyphenyl)-3-(4-fluorobenzoyl)benzo[b]thiophene
206434-77-7

6-methoxy-2-(4-methoxyphenyl)-3-(4-fluorobenzoyl)benzo[b]thiophene

Raloxifen
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 2 steps
1: 81 percent / BBr3 / CH2Cl2 / 3 h / 5 °C
2: 86 percent / NaH / dimethylformamide / 5 h / 50 °C
View Scheme
(2-dimethylamino-6-methoxy-benzo[b]thiophen-3-yl)-(4-fluoro-phenyl)-methanone
243845-88-7

(2-dimethylamino-6-methoxy-benzo[b]thiophen-3-yl)-(4-fluoro-phenyl)-methanone

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
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
Multi-step reaction with 3 steps
1: 83 percent / tetrahydrofuran / 1 h / 5 - 23 °C
2: 90 percent / NaH / dimethylformamide / 0.5 h / 20 °C
3: 78 percent / AlCl3; ethanethiol
View Scheme
Multi-step reaction with 3 steps
1: 97 percent / dimethylformamide / 0.25 h / 20 °C
2: 90 percent / tetrahydrofuran / 2 h / 5 - 23 °C
3: 78 percent / AlCl3; ethanethiol
View Scheme
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
63675-74-1

2-(4'-methoxyphenyl)-6-methoxybenzothiophene

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
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
Multi-step reaction with 4 steps
1: 71 percent / pyridine hydrochloride / 6 h / 220 °C
2: 99 percent / 4-(dimethylamino)pyridine, pyridine / Ambient temperature
3: 93 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / Heating
4: 42 percent / 5 N aq. NaOH / ethanol / 1.5 h / Heating
View Scheme
3-methoxybenzenethiol
15570-12-4

3-methoxybenzenethiol

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 80.4 percent / KOH / ethanol; H2O; ethyl acetate / Ambient temperature
2: 69 percent / PPA / 1 h / 85 - 90 °C
3: 71 percent / pyridine hydrochloride / 6 h / 220 °C
4: 99 percent / 4-(dimethylamino)pyridine, pyridine / Ambient temperature
5: 93 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / Heating
6: 42 percent / 5 N aq. NaOH / ethanol / 1.5 h / Heating
View Scheme
6-hydroxy-2-(4-hydroxyphenyl)benzo[B]-thiophene
63676-22-2

6-hydroxy-2-(4-hydroxyphenyl)benzo[B]-thiophene

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / 4-(dimethylamino)pyridine, pyridine / Ambient temperature
2: 93 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / Heating
3: 42 percent / 5 N aq. NaOH / ethanol / 1.5 h / Heating
View Scheme
4-(2-(piperidin-1-yl)ethoxy)benzoyl chloride
166975-76-4

4-(2-(piperidin-1-yl)ethoxy)benzoyl chloride

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / Heating
2: 42 percent / 5 N aq. NaOH / ethanol / 1.5 h / Heating
View Scheme
α-(3-methoxyphenyl-thio)-4-methoxyacetophenone
63675-73-0

α-(3-methoxyphenyl-thio)-4-methoxyacetophenone

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 69 percent / PPA / 1 h / 85 - 90 °C
2: 71 percent / pyridine hydrochloride / 6 h / 220 °C
3: 99 percent / 4-(dimethylamino)pyridine, pyridine / Ambient temperature
4: 93 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / Heating
5: 42 percent / 5 N aq. NaOH / ethanol / 1.5 h / Heating
View Scheme
6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothiophene
84449-65-0

6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothiophene

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / Heating
2: 42 percent / 5 N aq. NaOH / ethanol / 1.5 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: aluminum (III) chloride / 1,2-dichloro-ethane / 20.5 h / 20 °C / Inert atmosphere
2: sodium t-butanolate / acetonitrile / 16 h / 80 °C / Inert atmosphere
3: potassium hydroxide / dimethyl sulfoxide / Inert atmosphere
View Scheme
4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride
84449-80-9

4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2, DMF / toluene
2: 93 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / Heating
3: 42 percent / 5 N aq. NaOH / ethanol / 1.5 h / Heating
View Scheme
2-Bromo-4'-methoxyacetophenone
2632-13-5

2-Bromo-4'-methoxyacetophenone

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 80.4 percent / KOH / ethanol; H2O; ethyl acetate / Ambient temperature
2: 69 percent / PPA / 1 h / 85 - 90 °C
3: 71 percent / pyridine hydrochloride / 6 h / 220 °C
4: 99 percent / 4-(dimethylamino)pyridine, pyridine / Ambient temperature
5: 93 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / Heating
6: 42 percent / 5 N aq. NaOH / ethanol / 1.5 h / Heating
View Scheme
6-acetoxy-2-(4-acetoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride
84449-82-1

6-acetoxy-2-(4-acetoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
With sodium hydroxide In methanol; chloroform; water
With sodium hydroxide In methanol; chloroform; water
6-benzoyloxy-2-(4-benzoyloxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride
84449-83-2

6-benzoyloxy-2-(4-benzoyloxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
With methanesulfonic acid In ethanol; water
6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-piperidinoethoxy)-benzoyl]benzo[b]thiophene

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

A

C29H29NO6S2
1100049-65-7

C29H29NO6S2

B

C29H29NO6S2
1100049-66-8

C29H29NO6S2

C

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Stage #1: 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-piperidinoethoxy)-benzoyl]benzo[b]thiophene With sodium hydroxide; water In N,N-dimethyl-formamide at 80 - 90℃; for 3h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;
Stage #3: With ammonia In water; N,N-dimethyl-formamide Product distribution / selectivity;
Stage #1: 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-piperidinoethoxy)-benzoyl]benzo[b]thiophene With sodium hydroxide; water In tetrahydrofuran at 60 - 62℃; for 14h;
Stage #2: With acetic acid In tetrahydrofuran; water at 20℃; for 0.333333h;
Stage #3: With ammonia In tetrahydrofuran; water Product distribution / selectivity;
...Expand
C24H20O10S4
1390631-69-2

C24H20O10S4

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium t-butanolate / acetonitrile / 16 h / 80 °C / Inert atmosphere
2: potassium hydroxide / dimethyl sulfoxide / Inert atmosphere
View Scheme
methanesulfonic acid 4-chlorocarbonyl-phenyl ester
89938-63-6

methanesulfonic acid 4-chlorocarbonyl-phenyl ester

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aluminum (III) chloride / 1,2-dichloro-ethane / 20.5 h / 20 °C / Inert atmosphere
2: sodium t-butanolate / acetonitrile / 16 h / 80 °C / Inert atmosphere
3: potassium hydroxide / dimethyl sulfoxide / Inert atmosphere
View Scheme
methyl 4-hydroxylbenzoate
99-76-3

methyl 4-hydroxylbenzoate

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: potassium carbonate / acetone / Reflux
2: hydrogenchloride; water / tetrahydrofuran
3: thionyl chloride / dichloromethane
4: aluminum (III) chloride / dichloromethane / 12 h / 50 °C / Inert atmosphere
5: neat liquid / 12 h / Inert atmosphere; Reflux
6: aluminum (III) chloride / dichloromethane / 50 °C
View Scheme
4-(2-Chloroethoxy)benzoic acid methyl ester
38567-00-9

4-(2-Chloroethoxy)benzoic acid methyl ester

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogenchloride; water / tetrahydrofuran
2: thionyl chloride / dichloromethane
3: aluminum (III) chloride / dichloromethane / 12 h / 50 °C / Inert atmosphere
4: neat liquid / 12 h / Inert atmosphere; Reflux
5: aluminum (III) chloride / dichloromethane / 50 °C
View Scheme
4-(2-chloroethoxy)benzoic acid
65136-51-8

4-(2-chloroethoxy)benzoic acid

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: thionyl chloride / dichloromethane
2: aluminum (III) chloride / dichloromethane / 12 h / 50 °C / Inert atmosphere
3: neat liquid / 12 h / Inert atmosphere; Reflux
4: aluminum (III) chloride / dichloromethane / 50 °C
View Scheme
4-(2-chloro-ethoxy)-benzoyl chloride
65136-50-7

4-(2-chloro-ethoxy)-benzoyl chloride

Raloxifen
84449-90-1

Raloxifen

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aluminum (III) chloride / dichloromethane / 12 h / 50 °C / Inert atmosphere
2: neat liquid / 12 h / Inert atmosphere; Reflux
3: aluminum (III) chloride / dichloromethane / 50 °C
View Scheme
Raloxifen
84449-90-1

Raloxifen

[6-hydroxy-2-(4-hydroxyphenyl)-benzothiophene-3-yl]-[4-[2-(1-piperidyl)ethoxy]phenyl]methanone sulfamate
1326716-58-8

[6-hydroxy-2-(4-hydroxyphenyl)-benzothiophene-3-yl]-[4-[2-(1-piperidyl)ethoxy]phenyl]methanone sulfamate

Conditions
ConditionsYield
With aminosulfonic acid In water; acetonitrile at 80℃; Product distribution / selectivity;96.4%
Raloxifen
84449-90-1

Raloxifen

[2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanol
174731-13-6

[2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 6h;91%
Raloxifen
84449-90-1

Raloxifen

1-(2-(4-[6-Hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenoxy)-ethyl)-piperidinium bromide
1293408-87-3

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

Conditions
ConditionsYield
With hydrogen bromide In methanol; water at 1 - 35℃; pH=1.5; Reflux;87.4%
With hydrogen bromide In methanol; water at 35℃; pH=1.5; Reflux;87.4%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Raloxifen
84449-90-1

Raloxifen

Trifluoro-methanesulfonic acid 3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-2-(4-trifluoromethanesulfonyloxy-phenyl)-benzo[b]thiophen-6-yl ester

Trifluoro-methanesulfonic acid 3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-2-(4-trifluoromethanesulfonyloxy-phenyl)-benzo[b]thiophen-6-yl ester

Conditions
ConditionsYield
With triethylamine In 1,2-dichloro-ethane51%
With pyridine In dichloromethane at 0 - 20℃; for 1h;0.16 g
benzyl chloride
100-44-7

benzyl chloride

Raloxifen
84449-90-1

Raloxifen

A

[6-Benzyloxy-2-(4-hydroxy-phenyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone
189940-64-5

[6-Benzyloxy-2-(4-hydroxy-phenyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

B

[2-(4-Benzyloxy-phenyl)-6-hydroxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

[2-(4-Benzyloxy-phenyl)-6-hydroxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

C

6-benzyloxy-2-(4-benzyloxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene

6-benzyloxy-2-(4-benzyloxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamideA 20%
B 20%
C 20%
...Expand
Raloxifen
84449-90-1

Raloxifen

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

A

(6-((tert-butyldimethylsilyl)oxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone
174264-47-2

(6-((tert-butyldimethylsilyl)oxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone

B

2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-6-hydroxybenzo[b]thiophen-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl ketone
174264-46-1

2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-6-hydroxybenzo[b]thiophen-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl ketone

C

{6-(tert-Butyl-dimethyl-silanyloxy)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-benzo[b]thiophen-3-yl}-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

{6-(tert-Butyl-dimethyl-silanyloxy)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-benzo[b]thiophen-3-yl}-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Conditions
ConditionsYield
With dmap In tetrahydrofuran; N,N-dimethyl-formamideA 20%
B 20%
C 20%
...Expand
benzoyl chloride
98-88-4

benzoyl chloride

Raloxifen
84449-90-1

Raloxifen

4-(6-hydroxy-3-(4-(2-(piperidin-1-yl)ethoxy)phenylcarbonyl)benzo[b]thiophen-2-yl)phenyl benzoate
1248544-66-2

4-(6-hydroxy-3-(4-(2-(piperidin-1-yl)ethoxy)phenylcarbonyl)benzo[b]thiophen-2-yl)phenyl benzoate

Conditions
ConditionsYield
Stage #1: Raloxifen With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.0833333h;
Stage #2: benzoyl chloride In N,N-dimethyl-formamide at 20℃; for 0.25h;		7.8%
Raloxifen
84449-90-1

Raloxifen

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

A

(6-((tert-butyldimethylsilyl)oxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone
174264-47-2

(6-((tert-butyldimethylsilyl)oxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone

B

2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-6-hydroxybenzo[b]thiophen-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl ketone
174264-46-1

2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-6-hydroxybenzo[b]thiophen-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl ketone

Conditions
ConditionsYield
With dmap 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h; Yield given. Multistep reaction. Yields of byproduct given;
With dmap In tetrahydrofuran; N,N-dimethyl-formamide
...Expand
Raloxifen
84449-90-1

Raloxifen

[2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methane
166975-45-7

[2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / LiAlH4 / tetrahydrofuran / 6 h / 0 °C
2: 72 percent / Et3SiH, CF3CO2H / CH2Cl2 / 16 h / 0 °C
View Scheme
Raloxifen
84449-90-1

Raloxifen

[6-Hydroxy-2-(4-vinyl-phenyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

[6-Hydroxy-2-(4-vinyl-phenyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 20 percent / DMAP / tetrahydrofuran; dimethylformamide
2: 85 percent / Et3N / CH2Cl2
3: 1.) Pd(OAc)2, bis-diphenylphosphinopropane, Et3N, 2.) TBAF / 1) DMF; 2) CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 4 h / 100 °C
4: tetra-N-butylammoium fluoride / tetrahydrofuran / 3 h
View Scheme
Raloxifen
84449-90-1

Raloxifen

[2-(4-Ethynyl-phenyl)-6-hydroxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

[2-(4-Ethynyl-phenyl)-6-hydroxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 20 percent / DMAP / tetrahydrofuran; dimethylformamide
2: 85 percent / Et3N / CH2Cl2
3: 1.) Pd(OAc)2, bis-diphenylphosphinopropane, Et3N, 2.) TBAF / 1) DMF; 2) CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 10 h / 75 °C
4: tetra-N-butylammonium fluoride / tetrahydrofuran
View Scheme
Raloxifen
84449-90-1

Raloxifen

1-(4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-phenyl)-ethanone

1-(4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-phenyl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 20 percent / DMAP / tetrahydrofuran; dimethylformamide
2: 85 percent / Et3N / CH2Cl2
3: 1.) Pd(OAc)2, bis-diphenylphosphinopropane, Et3N, 2.) TBAF / 1) DMF; 2) CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 19 h / 80 °C
4: tetra-N-butylammonium fluoride / tetrahydrofuran / 3 h
View Scheme
Raloxifen
84449-90-1

Raloxifen

4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzamide

4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 20 percent / DMAP / tetrahydrofuran; dimethylformamide
2: 85 percent / Et3N / CH2Cl2
3: 1.) Pd(OAc)2, bis-diphenylphosphinopropane, Et3N, 2.) TBAF / 1) DMF; 2) CH2Cl2
4: NH3 / methanol
View Scheme
Multi-step reaction with 5 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: 54 percent / Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 4.5 h / 70 °C
4: MeAl(Cl)NH2 / toluene / Ambient temperature
5: 1N aq. HCl / tetrahydrofuran / 5 h / Heating
View Scheme
Raloxifen
84449-90-1

Raloxifen

4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzoic acid methyl ester
185416-94-8

4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 20 percent / DMAP / tetrahydrofuran; dimethylformamide
2: 85 percent / Et3N / CH2Cl2
3: 1.) Pd(OAc)2, bis-diphenylphosphinopropane, Et3N, 2.) TBAF / 1) DMF; 2) CH2Cl2
View Scheme
Multi-step reaction with 3 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: 27 percent / Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 4.5 h / 70 °C
View Scheme
Multi-step reaction with 4 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: 54 percent / Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 4.5 h / 70 °C
4: tetra-n-butylammonium fluoride / tetrahydrofuran
View Scheme
Raloxifen
84449-90-1

Raloxifen

4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-N,N-dimethyl-benzamide

4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-N,N-dimethyl-benzamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 20 percent / DMAP / tetrahydrofuran; dimethylformamide
2: 85 percent / Et3N / CH2Cl2
3: 1.) Pd(OAc)2, bis-diphenylphosphinopropane, Et3N, 2.) TBAF / 1) DMF; 2) CH2Cl2
4: Me3Al / toluene
View Scheme
Multi-step reaction with 5 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: 54 percent / Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 4.5 h / 70 °C
4: Me3Al / toluene / 21 h / 50 °C
5: tetra-N-butylammonium fluoride / tetrahydrofuran / 3 h
View Scheme
Raloxifen
84449-90-1

Raloxifen

4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzoic acid ethyl ester

4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzoic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 20 percent / DMAP / tetrahydrofuran; dimethylformamide
2: 85 percent / Et3N / CH2Cl2
3: 1.) Pd(OAc)2, bis-diphenylphosphinopropane, Et3N, 2.) TBAF / 1) DMF; 2) CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylformamide / 4.5 h / 70 °C
4: tetra-N-butylammonium fluoride / tetrahydrofuran / 3 h
View Scheme
Raloxifen
84449-90-1

Raloxifen

(4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-phenyl)-phosphonic acid diethyl ester

(4-{6-Hydroxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-phenyl)-phosphonic acid diethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 20 percent / DMAP / tetrahydrofuran; dimethylformamide
2: 85 percent / Et3N / CH2Cl2
3: 1.) Pd(PPh3)4, 2.) TBAF / 1) MeCN; 2) CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1: 1.) DMAP / 1.) THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 72 h
2: 88 percent / Et3N / 1,2-dichloro-ethane / Ambient temperature
3: Pd(PPh3)4, 2,6-lutidine / acetonitrile / 16 h / 70 °C
4: tetra-N-butylammonium fluoride / tetrahydrofuran / 3 h
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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