Fulvestrant supplier | CasNO.129453-61-8

Name
Fulvestrant
EINECS 642-998-6
CAS No. 129453-61-8
Article Data21
CAS DataBase
Density 1.201 g/cm³
Solubility
Melting Point 104-106°C
Formula C₃₂H₄₇F₅O₃S
Boiling Point 674.8 °C at 760 mmHg
Molecular Weight 606.781
Flash Point 361.9 °C
Transport Information
Appearance white powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Faslodex;Estra-1,3,5(10)-triene-3,17-diol,7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-, (7a,17b)-;ICI 182780;ZD 182780;ZD 9238;ZM 182780;
PSA 76.74000
LogP 9.54830

Synthetic route

: 153004-31-0
(+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
With dihydrogen peroxide; acetic acid In water; ethyl acetate at 40℃; for 4h; Inert atmosphere; Schlenk technique;	95%
Stage #1: (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol With β‐cyclodextrin In water; acetone at 20 - 60℃; for 0.5h; Stage #2: With N-Bromosuccinimide In water; acetone at 40℃; for 10h; Temperature;	87%
With dihydrogen peroxide; acetic acid In water; ethyl acetate for 6 - 8h;	85%

: 7β-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5-trien-3,17β-diol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
With dihydrogen peroxide; acetic acid In ethyl acetate	82%

: 1221256-46-7
(7R,13S)-3-methoxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
With aluminum (III) chloride; thiourea In dichloromethane at 20 - 55℃; Product distribution / selectivity;	32%

: 261506-24-5
ICI 182,780-17β-acetate

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
With methanol; potassium hydroxide at 20℃; for 3h; Product distribution / selectivity;

: 7-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5-trien-3,17β-diol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
With dihydrogen peroxide In water; acetic acid; ethyl acetate at 23℃; for 8h; Large scale reaction;	88.4 kg

: 148043-73-6
4,4,5,5,5-pentafluorpentan-1-ol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: isopropyl alcohol / 10 h / Reflux; Inert atmosphere 3: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C 4: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme
Multi-step reaction with 4 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 17 h / 0 - 20 °C 2.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C 3.1: hydrogenchloride / dichloromethane; methanol; water / 1 h 3.2: Reflux 4.1: acetic acid; dihydrogen peroxide / water; ethyl acetate View Scheme
Multi-step reaction with 4 steps 1: triethylamine; dmap / dichloromethane / 1 h / -10 °C 2: ethanol / 6 h / 65 °C 3: N,N-dimethyl-formamide / 20 °C 4: acetic acid; dihydrogen peroxide / ethyl acetate View Scheme

: 252947-01-6
1-methanesulfonyloxy-4,4,5,5,5-pentafluoropentane

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: isopropyl alcohol / 10 h / Reflux; Inert atmosphere 2: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C 3: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: ethanol / Reflux 2: sodium hydroxide / water; methanol / 24 h / Inert atmosphere; Reflux 3: sodium periodate / water; methanol / 24 h / 20 °C / Cooling with ice View Scheme

: 434-22-0
19-nortestosterone

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: potassium acetate; oxygen / N,N-dimethyl-formamide / 12 h / 20 - 120 °C / 6000.6 Torr / Autoclave 2.1: trichlorophosphate / dichloromethane / 4 h / 35 °C 3.1: potassium tert-butylate / toluene / 1 h / 20 - 50 °C 3.2: 3 h / 10 - 100 °C 4.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C 5.1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C 6.1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme
Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / 1 h / Reflux 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere 2.2: 2 h / 0 °C / Reflux; Inert atmosphere 3.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere 3.2: 0.5 h / -20 - 20 °C 4.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 5.1: water; sodium hydroxide / methanol / 5 h / 20 °C 6.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 7.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: toluene-4-sulfonic acid / 1 h / Reflux 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere 2.2: 2 h / 0 °C / Reflux; Inert atmosphere 3.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere 3.2: 0.5 h / -20 - 20 °C 4.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 5.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 6.1: water; sodium hydroxide / methanol / 5 h / 20 °C 7.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme

: 571-92-6
6-ketoestradiol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: trichlorophosphate / dichloromethane / 4 h / 35 °C 2.1: potassium tert-butylate / toluene / 1 h / 20 - 50 °C 2.2: 3 h / 10 - 100 °C 3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C 4.1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C 5.1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: trichlorophosphate / dichloromethane / 4 h / 35 °C
2.1: potassium tert-butylate / toluene / 1 h / 20 - 50 °C
2.2: 3 h / 10 - 100 °C
3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C
4.1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
5.1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme

: (8R,9S,13S,14S,17S)-3,17-Bis-(1-methoxy-1-methyl-ethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-6-one

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 1 h / 20 - 50 °C 1.2: 3 h / 10 - 100 °C 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C 3.1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C 4.1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: potassium tert-butylate / toluene / 1 h / 20 - 50 °C
1.2: 3 h / 10 - 100 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C
3.1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
4.1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme

: C35H55BrO5

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C 2: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C 3: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme

: C35H57BrO4

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C 2: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme

: C40H63F5O4S

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme

: carbamimidothioic acid 4,4,5,5,5-pentafluoropentyl mesylate ester

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C 2: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C View Scheme

: 875573-66-3
(+)-(7α)-[9-bromononyl]estra-1,3,5(10)-triene-3-ol-17β-yl acetate

: 148757-88-4
4,4,5,5,5-pentafluoro-1-pentanethiol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique 2: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique View Scheme

: 160598-75-4
1-(acetylsulfanyl)-4,4,5,5,5-pentafluoropentane

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol / 0.33 h / 20 °C / Inert atmosphere; Schlenk technique 2: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique 3: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique View Scheme

: 89359-54-6
9-bromo-1-nonene

: 129453-61-8
fulvestrant

Conditions

Yield

Multi-step reaction with 4 steps
1.1: Schwartz's reagent / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Schlenk technique
1.2: 0.17 h / 20 °C / Inert atmosphere; Schlenk technique
1.3: 20 °C / Inert atmosphere; Schlenk technique
2.1: lithium bromide; copper(ll) bromide / acetonitrile / 2 h / 20 °C / Inert atmosphere; Schlenk technique
3.1: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique
4.1: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique
View Scheme

: 2590-41-2
6-dehydro-19-nortestosterone acetate

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Schwartz's reagent / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: 0.17 h / 20 °C / Inert atmosphere; Schlenk technique 1.3: 20 °C / Inert atmosphere; Schlenk technique 2.1: lithium bromide; copper(ll) bromide / acetonitrile / 2 h / 20 °C / Inert atmosphere; Schlenk technique 3.1: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique 4.1: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique View Scheme
Multi-step reaction with 5 steps 1.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere 1.2: 0.5 h / -20 - 20 °C 2.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 3.1: water; sodium hydroxide / methanol / 5 h / 20 °C 4.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 5.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere 1.2: 0.5 h / -20 - 20 °C 2.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 3.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 4.1: water; sodium hydroxide / methanol / 5 h / 20 °C 5.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme

: 875573-63-0
(+)-3-oxo-(7α)-[9-bromononyl]estr-4-en-17β-ylacetate

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium bromide; copper(ll) bromide / acetonitrile / 2 h / 20 °C / Inert atmosphere; Schlenk technique 2: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique 3: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique View Scheme
Multi-step reaction with 4 steps 1: copper(ll) bromide; lithium bromide / acetonitrile / 3 h / 20 °C / Large scale 2: hydrogen bromide / methanol / 3 h / Reflux; Large scale 3: sodium hydroxide / N,N-dimethyl-formamide; water / 1.5 h / 0 - 15 °C / Large scale 4: acetic acid; dihydrogen peroxide / ethyl acetate / 8 h / 20 - 30 °C / Large scale View Scheme

: C37H55BrO5

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C 2.1: hydrogenchloride / dichloromethane; methanol; water / 1 h 2.2: Reflux 3.1: acetic acid; dihydrogen peroxide / water; ethyl acetate View Scheme

: 862700-61-6
thiobenzoic acid S-(4,4,5,5,5-pentafluoro-pentyl)ester

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C 2.1: hydrogenchloride / dichloromethane; methanol; water / 1 h 2.2: Reflux 3.1: acetic acid; dihydrogen peroxide / water; ethyl acetate View Scheme

: 122566-22-7
(8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-ol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: pyridine; Dess-Martin periodane / dichloromethane / 1 h / 20 °C 2.1: triethyl borane; potassium tert-butylate / toluene; tetrahydrofuran / 0.17 h / 110 °C 2.2: Reflux 3.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C 4.1: hydrogenchloride / dichloromethane; methanol; water / 1 h 4.2: Reflux 5.1: acetic acid; dihydrogen peroxide / water; ethyl acetate View Scheme

Yield

Multi-step reaction with 5 steps
1.1: pyridine; Dess-Martin periodane / dichloromethane / 1 h / 20 °C
2.1: triethyl borane; potassium tert-butylate / toluene; tetrahydrofuran / 0.17 h / 110 °C
2.2: Reflux
3.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C
4.1: hydrogenchloride / dichloromethane; methanol; water / 1 h
4.2: Reflux
5.1: acetic acid; dihydrogen peroxide / water; ethyl acetate
View Scheme

: 53573-82-3
3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene-6-one

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethyl borane; potassium tert-butylate / toluene; tetrahydrofuran / 0.17 h / 110 °C 1.2: Reflux 2.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C 3.1: hydrogenchloride / dichloromethane; methanol; water / 1 h 3.2: Reflux 4.1: acetic acid; dihydrogen peroxide / water; ethyl acetate View Scheme

: C29H44O3

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 2: water; sodium hydroxide / methanol / 5 h / 20 °C 3: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 4: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 2: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 3: water; sodium hydroxide / methanol / 5 h / 20 °C 4: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme

: C31H44O4

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: water; sodium hydroxide / methanol / 5 h / 20 °C 2: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 3: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 2: water; sodium hydroxide / methanol / 5 h / 20 °C 3: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme

: C27H40O2

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 2: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme

: C36H51F5O4S

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water; sodium hydroxide / methanol / 5 h / 20 °C 2: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; dihydrogen peroxide / ethyl acetate / 0 - 25 °C 2: sodium hydroxide / methanol / 25 °C View Scheme

: 148757-88-4
4,4,5,5,5-pentafluoro-1-pentanethiol

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 2: water; sodium hydroxide / methanol / 5 h / 20 °C 3: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme

: 4999-76-2
3,17β-diacetoxy-estra-3,5-diene

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere 1.2: 2 h / 0 °C / Reflux; Inert atmosphere 2.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere 2.2: 0.5 h / -20 - 20 °C 3.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 4.1: water; sodium hydroxide / methanol / 5 h / 20 °C 5.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 6.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere 1.2: 2 h / 0 °C / Reflux; Inert atmosphere 2.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere 2.2: 0.5 h / -20 - 20 °C 3.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 4.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation 5.1: water; sodium hydroxide / methanol / 5 h / 20 °C 6.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere
1.2: 2 h / 0 °C / Reflux; Inert atmosphere
2.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere
2.2: 0.5 h / -20 - 20 °C
3.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
4.1: water; sodium hydroxide / methanol / 5 h / 20 °C
5.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
6.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme

Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere
1.2: 2 h / 0 °C / Reflux; Inert atmosphere
2.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere
2.2: 0.5 h / -20 - 20 °C
3.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
4.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
5.1: water; sodium hydroxide / methanol / 5 h / 20 °C
6.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme

: C11H10F5NO5S

: 129453-61-8
fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 6 h / 65 °C 2: N,N-dimethyl-formamide / 20 °C 3: acetic acid; dihydrogen peroxide / ethyl acetate View Scheme

: 129453-61-8
fulvestrant

: 109-94-4
formic acid ethyl ester

: 403656-82-6
ICI 182,780-17β-formate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid Heating;	100%

: 98-88-4
benzoyl chloride

: 129453-61-8
fulvestrant

: 261506-25-6
ICI 182,780-3-benzoate

Conditions

Conditions	Yield
With potassium hydroxide In dichloromethane at 0 - 20℃; for 2.5h; Schotten-Baumann reaction;	99%
With potassium hydroxide In dichloromethane Esterification;

: 141-78-6
ethyl acetate

: 129453-61-8
fulvestrant

: 261506-24-5
ICI 182,780-17β-acetate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 6h; Heating;	97%

: 129453-61-8
fulvestrant

: 229625-50-7
di-tert-butyl chloromethyl phosphate

: di-tert-butyl ((7R,8R,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentyl sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxy)methyl phosphate

Conditions

Conditions	Yield
Stage #1: fulvestrant With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.0833333h; Inert atmosphere; Stage #2: di-tert-butyl chloromethyl phosphate In tetrahydrofuran at 70℃;	95.38%

: 129453-61-8
fulvestrant

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-deca hydro-6H-cyclopenta[a]phenanthren-3-yl sulfurofluoridate

Conditions

Conditions	Yield
With fluorosulfonyl fluoride; triethylamine In acetonitrile at 20℃; for 1h; chemoselective reaction;	90%
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 12h; Sealed tube;	72%

: 103366-74-1
2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate

: 129453-61-8
fulvestrant

: C84H131F5O21S

Conditions

Conditions	Yield
Stage #1: fulvestrant With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at -20℃; Stage #2: 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate In 1,2-dichloro-ethane Further stages.;	80%

: 129453-61-8
fulvestrant

: ICI 182,780-17-ketone

Conditions

Conditions	Yield
With oxalyl dichloride; dimethyl sulfoxide; diisopropylamine In 1,2-dichloro-ethane at -70 - 20℃; Swern oxidation;	65%

: 990-91-0
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

: 129453-61-8
fulvestrant

: dibenzyl ((7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl) phosphate

Conditions

Conditions	Yield
Stage #1: fulvestrant With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.0833333h; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at 70℃; for 18h;	62.99%

: 10417-94-4
all cis-5,8,11,14,17-eicosapentaenoic acid

: 129453-61-8
fulvestrant

: C52H75F5O4S

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	58%

: 108-30-5
succinic acid anhydride

: 129453-61-8
fulvestrant

: 4-(((7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)-4-oxobutanoic acid

Conditions

Conditions	Yield
With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 16h;	54.08%

: 5070-13-3
bis-(p-nitrophenyl) carbonate

: 13518-40-6
L-valine tert-butylester hydrochloride

: 129453-61-8
fulvestrant

: (2S)-tert-butyl 2-(((7R,8R,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H cyclopenta[a]phenanthren-3-yloxy)carbonylamino)-3-methylbutanoate

Conditions

Conditions	Yield
Stage #1: bis-(p-nitrophenyl) carbonate; L-valine tert-butylester hydrochloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: fulvestrant With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	48.8%

...Expand

: 1118-68-9
dimethylaminoacetic acid

: 129453-61-8
fulvestrant

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl dimethylglycinate

Conditions

Conditions	Yield
Stage #1: dimethylaminoacetic acid; fulvestrant With dmap In dichloromethane at 0℃; for 0.166667h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;	46.77%

: 5070-13-3
bis-(p-nitrophenyl) carbonate

: 16874-17-2
L-phenylalanine tert-butyl ester

: 129453-61-8
fulvestrant

: (2S)-tert-butyl 2-(((7R,8R,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoro pentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxy)carbonylamino)-3-phenylpropanoate

Conditions

Conditions	Yield
Stage #1: bis-(p-nitrophenyl) carbonate; L-phenylalanine tert-butyl ester With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: fulvestrant With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere;	33.96%

...Expand

: 3235-69-6
morpholin-4-ylacetic acid

: 129453-61-8
fulvestrant

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 2-morpholinoacetate

Conditions

Conditions	Yield
Stage #1: morpholin-4-ylacetic acid; fulvestrant With dmap In dichloromethane at 0℃; for 0.0833333h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	33.07%

: 39539-66-7
4-methyl-piperazine-1-carbonyl chloride

: 129453-61-8
fulvestrant

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 4-methylpiperazine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: fulvestrant With dmap; potassium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: 4-methyl-piperazine-1-carbonyl chloride at 0 - 20℃; for 18h;	31.46%

: 112-37-8
undecylenic acid

: 129453-61-8
fulvestrant

: C43H67F5O4S

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	27.7%

: 4497-04-5
3-morpholin-4-ylpropionic acid

: 129453-61-8
fulvestrant

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 3-morpholinopropanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;	26.37%

: 129453-61-8
fulvestrant

: 229625-50-7
di-tert-butyl chloromethyl phosphate

: di-tert-butyl ((((7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl- 7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)methyl) phosphate

Conditions

Conditions	Yield
Stage #1: fulvestrant With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.25h; Stage #2: di-tert-butyl chloromethyl phosphate In tetrahydrofuran at 70℃; for 7h;	26.14%

: 814-49-3
diethyl chlorophosphate

: 129453-61-8
fulvestrant

: diethyl ((7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl) phosphate

Conditions

Conditions	Yield
Stage #1: fulvestrant With tetrabutylammomium bromide; sodium hydroxide In chloroform; water at 20℃; for 0.5h; Stage #2: diethyl chlorophosphate In chloroform; water at 20℃; for 16h;	24.5%

: 129453-61-8
fulvestrant

: 54699-92-2
(4-Methyl-piperazin-1-yl)-acetic acid

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 2-(4-methylpiperazin-1-yl)acetate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h;	24.37%

: 37386-15-5
2-(pyrrolidin-1-yl)acetic acid

: 129453-61-8
fulvestrant

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 2-(pyrrolidin-1-yl)acetate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;	23.24%

: 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid

: 129453-61-8
fulvestrant

: C50H81F5O4S

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	23.2%

: 57-10-3
1-hexadecylcarboxylic acid

: 129453-61-8
fulvestrant

: C48H77F5O4S

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	22%

: 15790-93-9, 15790-94-0, 4189-02-0
undec-2-enoic acid

: 129453-61-8
fulvestrant

: C43H65F5O4S

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	21.5%

: 129453-61-8
fulvestrant

: docosahexa-4,7,10,13,16,19-enoic acid

: C54H77F5O4S

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	21.1%

: 129453-61-8
fulvestrant

: 69-72-7
salicylic acid

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 2-hydroxybenzoate

Conditions

Conditions	Yield
Stage #1: fulvestrant; salicylic acid With dmap In dichloromethane at 0℃; for 0.0833333h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;	18.92%

: 6300-04-5
3-dimethylaminopropionic acid

: 129453-61-8
fulvestrant

: (7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 3-(dimethylamino)propanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h;	18.62%

Fulvestrant Chemical Properties

Structure of Fulvestrant (CAS NO.129453-61-8):

IUPAC Name: (7R,8R,9S,13S,14S,17S)-13-Methyl-7-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-7,8,9,11,12,14,15,16,
17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Molecular Formula: C₃₂H₄₇F₅O₃S
Molar Mass: 606.77 g/mol
Flash Point: 361.9 °C
Boiling Point: 674.8°C at 760 mmHg
Vapour Pressure: 3.95E-19 mmHg at 25 °C
Density: 1.201 g/cm³
Storage Temp.: 2-8 °C
Index of Refraction: 1.521
Molar Refractivity: 154.04 cm³
Molar Volume: 505.1 cm³
Surface Tension: 41.9 dyne/cm
XLogP3: 9.2
H-Bond Donor: 2
H-Bond Acceptor: 8
Rotatable Bond Count: 14
Tautomer Count: 9
Exact Mass: 606.316607
MonoIsotopic Mass: 606.316607
Topological Polar Surface Area: 57.5
Heavy Atom Count: 41
Canonical SMILES: CC12CCC3C(C1CCC2O)C(CC4=C3C=CC(=C4)O)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F
Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)[C@@H](CC4=C3C=CC(=C4)O)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F
InChI: InChI=1S/C32H47F5O3S/c1-30-17-15-26-25-12-11-24(38)21-23(25)20-22(29(26)27(30)13-14-28(30)39)10-7-5-3-2-4-6-8-18-41(40)19-9-16-31(33,34)32(35,36)37/h11-12,21-22,26-29,38-39H,2-10,13-20H2,1H3/t22-,26-27+,28+,29-,30+,41/m1/s1
InChIKey: VWUXBMIQPBEWFH-WCCTWKNTSA-N
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals; Nuclear Receptors

Fulvestrant Uses

Fulvestrant (CAS NO.129453-61-8) is indicated for the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following anti-estrogen therapy.

Fulvestrant Safety Profile

RTECS: KG7623000

Fulvestrant Specification

Fulvestrant (CAS NO.129453-61-8) is also named as 7alpha-(9-((4,4,5,5,5-Pentafluoropentyl)sulfinyl)nonyl)estra-1,3,5(10)-triene-3,17beta-diol ; CCRIS 8741 ; Faslodex ; HSDB 7658 ; ICI 182,780 ; ICI 182780 ; UNII-22X328QOC4 ; ZM 182780 . Fulvestrant (CAS NO.129453-61-8) is white powder.

Product Name

Fulvestrant

Synthetic route

Fulvestrant Chemical Properties

Fulvestrant Uses

Fulvestrant Safety Profile

Fulvestrant Specification

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