Product Name

  • Name

    Raloxifene hydrochloride

  • EINECS 639-789-7
  • CAS No. 82640-04-8
  • Article Data24
  • CAS DataBase
  • Density 1.285g/cm3
  • Solubility DMSO: 28 mg/mL, soluble
  • Melting Point 143-147oC
  • Formula C28H28ClNO4S
  • Boiling Point 728.2 °C at 760 mmHg
  • Molecular Weight 510.054
  • Flash Point 394.2 °C
  • Transport Information
  • Appearance Light yellow solid
  • Safety 22-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 82640-04-8 (Raloxifene hydrochloride)
  • Hazard Symbols IrritantXi
  • Synonyms Methanone,[6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-,hydrochloride (9CI);Bonebay;Bontact;Evista;Fiona;Keoxifene hydrochloride;LY 156758;Ralofen;Reloxafine;Raloxifene HCl;
  • PSA 98.24000
  • LogP 6.81510

Synthetic route

[2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride
84541-36-6

[2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride

raloxifene hydrochloride

raloxifene hydrochloride

Conditions
ConditionsYield
Stage #1: [2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride With boron trichloride In dichloromethane at 2 - 20℃; for 52.25h;
Stage #2: With methanol In dichloromethane at 12℃; for 1.08333h; Product distribution / selectivity; Reflux;		95%
Stage #1: [2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride With boron tribromide In dichloromethane at 2 - 20℃; for 52.25h;
Stage #2: With methanol In dichloromethane for 0.75h; Product distribution / selectivity; Reflux;		95%
With boron trichloride In dichloromethane at 0 - 22℃; for 38.1h; Product distribution / selectivity; Reflux;92.6%
With aluminium trichloride; ethanethiol In dichloromethane for 0.5h; Ambient temperature;77.5%
[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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
With N,N-diethylaniline; ethanethiol In dichloromethane at 32 - 34℃; for 2h; Solvent;92%

4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride
84449-80-9

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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Stage #1: 4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride With pyridine; thionyl chloride In dichloromethane for 1h; Heating / reflux;
Stage #2: 6-acetoxy-2-(4-acetoxyphenyl)benzo[b]thiophene In dichloromethane
Stage #3: With hydrogenchloride; sodium hydroxide; water; aluminum (III) chloride more than 3 stages;		70.4%
3-methoxybenzenethiol
15570-12-4

3-methoxybenzenethiol

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80.4 percent / KOH / ethanol; H2O; ethyl acetate / Ambient temperature
2: 69 percent / PPA / 1 h / 85 - 90 °C
3: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
4: 77.5 percent / AlCl3, EtSH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1.1: bromine / methanol / 2.5 h / 10 °C
1.2: 4 h / 0 - 20 °C
2.1: polyphosphoric acid / 2 h / 65 - 90 °C
3.1: thionyl chloride / N,N-dimethyl-formamide; toluene / 2 h / 80 °C
3.2: 3 h / 20 °C
View Scheme
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
63675-74-1

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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
2: 77.5 percent / AlCl3, EtSH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
4-(2-(piperidin-1-yl)ethoxy)benzoyl chloride
166975-76-4

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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
2: 77.5 percent / AlCl3, EtSH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
α-(3-methoxyphenyl-thio)-4-methoxyacetophenone
63675-73-0

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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 69 percent / PPA / 1 h / 85 - 90 °C
2: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
3: 77.5 percent / AlCl3, EtSH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride
84449-80-9

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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2, DMF / toluene
2: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
3: 77.5 percent / AlCl3, EtSH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1.1: thionyl chloride / dichloromethane / 40 °C
2.1: aluminum (III) chloride / dichloromethane / 10 - 35 °C
3.1: potassium hydroxide; water / 105 - 110 °C
3.2: 60 °C / pH 2
View Scheme
2-Bromo-4'-methoxyacetophenone
2632-13-5

2-Bromo-4'-methoxyacetophenone

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80.4 percent / KOH / ethanol; H2O; ethyl acetate / Ambient temperature
2: 69 percent / PPA / 1 h / 85 - 90 °C
3: AlCl3 / CH2Cl2 / 1.5 h / 27 - 29 °C
4: 77.5 percent / AlCl3, EtSH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
63675-74-1

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

4-[2-(piperidin-1-yl)ethoxy]benzoyl chloride hydrochloride

4-[2-(piperidin-1-yl)ethoxy]benzoyl chloride hydrochloride

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
With boron trichloride In 1,2-dichloro-ethane at 0 - 35℃; for 24h;
aqueous sodium chloride

aqueous sodium chloride

2-(4'-methoxyphenyl)-6-methoxybenzothiophene
63675-74-1

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

4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride
84449-80-9

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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; thionyl chloride; ethanethiol; aluminium trichloride In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene
With hydrogenchloride; thionyl chloride; ethanethiol; aluminium trichloride In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene
With hydrogenchloride; thionyl chloride; ethanethiol; aluminium trichloride In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene
With hydrogenchloride; thionyl chloride; ethanethiol; aluminium trichloride In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene
With hydrogenchloride; CO; thionyl chloride; ethanethiol; aluminium trichloride In tetrahydrofuran; N-methyl-acetamide; dichloromethane; water; chlorobenzene
...Expand
2-(4'-methoxyphenyl)-6-methoxybenzothiophene
63675-74-1

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

4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride
84449-80-9

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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
With thionyl chloride; ethanethiol; aluminium trichloride In tetrahydrofuran; N-methyl-acetamide; dichloromethane; chlorobenzene
With thionyl chloride; ethanethiol; aluminium trichloride In tetrahydrofuran; N-methyl-acetamide; dichloromethane; chlorobenzene
Stage #1: 4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride With thionyl chloride; N,N-dimethyl-formamide In chlorobenzene at 70 - 75℃; for 1h;
Stage #2: 2-(4'-methoxyphenyl)-6-methoxybenzothiophene With aluminum (III) chloride In dichloromethane; chlorobenzene at 20℃; for 1.75h;
Stage #1: 4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride With thionyl chloride In N,N-dimethyl-formamide; toluene at 80℃; for 2h;
Stage #2: 2-(4'-methoxyphenyl)-6-methoxybenzothiophene With aluminum (III) chloride In dichloromethane at 20℃; for 3h;
Raloxifen
84449-90-1

Raloxifen

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; isopropyl alcohol at 5 - 35℃; for 2.25h;
With ammonium chloride In water at 70 - 75℃; for 8.45h; Product distribution / selectivity;
With hydrogenchloride In tetrahydrofuran Product distribution / selectivity;
With hydrogenchloride In methanol; water pH=2;
Stage #1: Raloxifen In methanol; acetone at 25 - 30℃; for 0.166667h;
Stage #2: With hydrogenchloride In methanol; water; acetone pH=1.5 - Ca. 2;
<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

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Stage #1: <6-<(methylsulfonyl)oxy>-2-<4-<(methylsulfonyl)oxy>phenyl>benzothien-3-yl><4-<2-(1-pyrrolidinyl)ethoxy>phenyl>methanone hydrochloride With water; potassium hydroxide at 105 - 110℃;
Stage #2: With hydrogenchloride In water; acetone at 60℃; pH=2;
Ethyl 4-hydroxybenzoate
120-47-8

Ethyl 4-hydroxybenzoate

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / ethyl acetate; water / 13 - 35 °C / Reflux
2.1: formic acid; sulfuric acid / acetic acid
3.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C
4.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C
4.2: 62 - 66 °C / Inert atmosphere
5.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux
5.2: 20 °C
6.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
6.2: 2 - 51 °C
7.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C
7.2: 1.08 h / 12 °C / Reflux
View Scheme
N-chloroethylpiperidine hydrochloride
2008-75-5

N-chloroethylpiperidine hydrochloride

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
1.2: 2 - 51 °C
2.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C
2.2: 1.08 h / 12 °C / Reflux
View Scheme
[6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl](4-hydroxyphenyl)methanone
63676-19-7

[6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl](4-hydroxyphenyl)methanone

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
1.2: 2 - 51 °C
2.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C
2.2: 1.08 h / 12 °C / Reflux
View Scheme
ethyl 4-((phenylsulfonyl)oxy)benzoate

ethyl 4-((phenylsulfonyl)oxy)benzoate

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: formic acid; sulfuric acid / acetic acid
2.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C
3.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C
3.2: 62 - 66 °C / Inert atmosphere
4.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux
4.2: 20 °C
5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
5.2: 2 - 51 °C
6.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C
6.2: 1.08 h / 12 °C / Reflux
View Scheme
p-benzenesulfonyloxybenzoyl chloride

p-benzenesulfonyloxybenzoyl chloride

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C
1.2: 62 - 66 °C / Inert atmosphere
2.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux
2.2: 20 °C
3.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
3.2: 2 - 51 °C
4.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C
4.2: 1.08 h / 12 °C / Reflux
View Scheme
benzenesulfonic acid-4-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenyl ester
1293362-49-8

benzenesulfonic acid-4-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophene-3-carbonyl]-phenyl ester

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux
1.2: 20 °C
2.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
2.2: 2 - 51 °C
3.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C
3.2: 1.08 h / 12 °C / Reflux
View Scheme
4-benzenesulfonyloxy-benzoic acid
7507-41-7

4-benzenesulfonyloxy-benzoic acid

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C
2.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C
2.2: 62 - 66 °C / Inert atmosphere
3.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux
3.2: 20 °C
4.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C
4.2: 2 - 51 °C
5.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C
5.2: 1.08 h / 12 °C / Reflux
View Scheme
1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine / methanol / 2.5 h / 10 °C
1.2: 4 h / 0 - 20 °C
2.1: polyphosphoric acid / 2 h / 65 - 90 °C
3.1: thionyl chloride / N,N-dimethyl-formamide; toluene / 2 h / 80 °C
3.2: 3 h / 20 °C
View Scheme
1-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-2-(2-benzylthio-4-methoxyphenyl)ethanone

1-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-2-(2-benzylthio-4-methoxyphenyl)ethanone

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoroacetic acid / 6 h / 80 °C
2: N,N-diethylaniline / dichloromethane / 12 h / 40 °C
3: N,N-diethylaniline; ethanethiol / dichloromethane / 2 h / 32 - 34 °C
View Scheme
benzyl-(3-methoxyphenyl)-sulfide

benzyl-(3-methoxyphenyl)-sulfide

raloxifene hydrochloride
82640-04-8

raloxifene hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: periodic acid; iron(III) chloride / toluene / 4 h / 27 °C / Cooling with ice
2: trifluorormethanesulfonic acid / 6 h / 70 °C
3: trifluoroacetic acid / 6 h / 80 °C
4: N,N-diethylaniline / dichloromethane / 12 h / 40 °C
5: N,N-diethylaniline; ethanethiol / dichloromethane / 2 h / 32 - 34 °C
View Scheme

Raloxifene hydrochloride Chemical Properties

Structure of Raloxifene hydrochloride (CAS NO.82640-04-8):

Empirical Formula: C28H28ClNO4S
Molecular Weight: 510.0442
Nominal Mass: 509 Da
Average Mass: 510.0442 Da
Monoisotopic Mass: 509.142756 Da 
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
Solubility: DMSO: 28 mg/mL, soluble
Appearance: Light yellow solid
IUPAC Name: [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone hydrochloride
Canonical SMILES: C1CCN(CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)O)C5=CC=C(C=C5)O.Cl
InChI: InChI=1S/C28H27NO4S.ClH/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;1H
InChIKey: BKXVVCILCIUCLG-UHFFFAOYSA-N
Product Category of Raloxifene hydrochloride (CAS NO.82640-04-8): Active Pharmaceutical Ingredients;Raloxifene;Intracellular receptor

Raloxifene hydrochloride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
women TDLo oral 36mg/kg/30D-I (36mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

LIVER: LIVER FUNCTION TESTS IMPAIRED		 Lancet. Vol. 352, Pg. 1524, 1998.

Raloxifene hydrochloride Safety Profile

Hazard Codes: IrritantXi
Risk Statements of Raloxifene hydrochloride (CAS NO.82640-04-8): 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.

Raloxifene hydrochloride Specification

 Raloxifene hydrochloride , its cas register number is 82640-04-8. It also can be called [6-Hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone hydrochloride ; and Keoxifene hydrochloride .

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