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84449-90-1 Methanone,[6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-
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84449-90-1 Usage

Application in Particular Diseases

In Osteoporosis: Raloxifene is an estrogen agonist on bone but an antagonist on the breast and uterus. It is approved for prevention and treatment of postmenopausal osteoporosis. Other estrogen agonists/antagonists may be approved soon (e.g., bazedoxifene, lasofoxifene). Raloxifene decreases vertebral fractures and increases spine and hip BMD, but to a lesser extent than bisphosphonates. After discontinuation, the beneficial effect is lost and bone loss returns to age- or disease-related rates. Raloxifene (like tamoxifen) is associated with decreased breast cancer risk. Raloxifene is associated with decreases in total and low-density lipoprotein cholesterol, neutral effects on high-density lipoprotein cholesterol, but slight increases in triglycerides; no beneficial cardiovascular effects have yet been demonstrated. Raloxifene is well tolerated overall. Hot flushes occur more frequently in women recently finishing menopause or discontinuing estrogen therapy (ET). Endometrial bleeding occurs rarely. Raloxifene is contraindicated in women with an active or past history of venous thromboembolism. Therapy should be stopped if a patient anticipates extended immobility.

Chemical Properties

Light-Yellow Solid

Uses

A nonsteroidal estrogen receptor mixed agonist/antagonist

Uses

Raloxifene is a nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic.

Indications

Raloxifene (Evista) is a new SERM approved for use in the treatment and prevention of osteoporosis because it has estrogenic activity in bone. Raloxifene is an estrogen antagonist in both breast and endometrial tissues. The estrogenlike properties of raloxifene result in the maintenance of a favorable serum lipid profile (decreased low-density lipoprotein levels with no change in either high-density lipoproteins or triglycerides). Raloxifene is 95% bound to plasma proteins. Absorption of raloxifene is impaired by cholestyramine.

Definition

ChEBI: A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogens at positions 2, 3, and 6 have been replaced by p-hydroxyphenyl, p-[2-(piperidin-1-yl)ethoxy]benzoyl, and hydroxy groups, respectively.

Brand name

Evista (Lilly).

General Description

Raloxifene, [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone (Evista), is a benzothiophene derivativethat differs slightly from the triphenylethyleneSERMs. A key structural difference is the carbonyl “hinge”that connects the modified phenolic side chain to the benzothiophenering system. This hinge is the key structural elementthat leads to the differing actions at the ERs.Raloxifene, unlike tamoxifen and toremifene, has antagonistproperties on the endometrium and breast tissue and agonistproperties on bone and the cardiovascular system. The lackof agonist action on endometrial tissue has been suggestedas a reason for the lack of endometrial cancer associatedwith raloxifene use. Raloxifene is approved for the preventionand treatment of osteoporosis in postmenopausalwomen. It has also been investigated for preventing breastcancer in comparison with tamoxifen. Recent studies indicatesthat it has similar effectiveness to tamoxifen, but has apreferable side effect profile.

Biological Activity

Selective estrogen receptor modulator (SERM) that binds to ER α and ER β , and tissue-dependently activates or blocks estrogen-induced transcription. Acts as an antiestrogen in breast and uterine tissue, but displays estrogen agonist activity in bone. In D12 rat hypothalamic cells, inhibits progesterone receptor induction by estrogen with an IC 50 of 1 nM.

Clinical Use

Raloxifene, the first SERM approved for the prevention of osteoporosis in postmenopausal women, acts as an estrogen agonist on receptors in osteoblasts and osteoclasts but as an antagonist at breast and uterine estrogen receptors.
InChI:InChI=1/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2

84449-90-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name raloxifene

1.2 Other means of identification

Product number -
Other names [3H]-Raloxifene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:84449-90-1 SDS

84449-90-1Synthetic 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;
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%
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%
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
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
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