855-19-6

Basic information

• Product Name: 4-Chlorotestosterone acetate
• Synonyms: CLOSTEBOL ACETATE;4-ANDROSTEN-4-CHLORO-17BETA-OL-3-ONE 17-ACETATE;4-ANDROSTEN-4-CHLORO-17-BETA-OL-3-ONE ACETATE;4-chloroandrost-4-ene-17beta-ol-3-one acetate;4-CHLOROTESTOSTERONE ACETATE;STERANABOL;TURINABOL;4-chloro-17-beta-hydroxy-androst-4-en-3-onacetate
• CAS NO: 855-19-6
• Molecular Formula: C₂₁H₂₉ClO₃
• Molecular Weight: 364.91
• EINECS: 212-720-4
• Product Categories: Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone;API
• Mol File: 855-19-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 228-230°
• Boiling Point: 457.2 °C at 760 mmHg
• Flash Point: 155.7 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 1.52E-08mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Chlorotestosterone acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorotestosterone acetate(855-19-6)
• EPA Substance Registry System: 4-Chlorotestosterone acetate(855-19-6)

Safety Data

• Hazardous Substances Data: 855-19-6(Hazardous Substances Data)

Usage

Originator

Clostebol acetate,Hunan Steroid

Uses

Clostebol acetate is an anabolic steroid. This is a controlled substance.

Manufacturing Process

15 g of a mixture of 4β,5-epoxy-etiocholane-17β-ol-3-one and 4β,5-epoxyandrostane-17β-ol-3-one, dissolved in 375 ml chloroform, are treated with a stream of gaseous HCl at room temperature for about 2 h. The chloroform solution is neutralized with a sodium bicarbonate solution, washed with water and dried. The residue is crystallized from benzene or aqueous methanol and 9 g of needle-shaped crystals of 4-chloro-testosterone, melting point 186°- 188°C, are obtained. Upon concentrating the mother-liquor, 3.2 g of thisproduct, melting point 180°-184°C, are covered. 1 g 4-chloro-testosterone are acetylated with 1 ml acetic anhydride and 5 ml pyridine at room temperature for 16 h. Ice is added to the solution, and the precipitate is filtered off and recrystallized from chloroform-ethanol; 1 g 4- chloro-testosterone-acetate, melting point 228°-230°C, is obtained.

Hazard

A poison by ingestion. A reproductive hazard.

InChI:InChI=1/C21H29ClO3/c1-12(23)25-18-7-6-14-13-4-5-16-19(22)17(24)9-11-20(16,2)15(13)8-10-21(14,18)3/h13-15,18H,4-11H2,1-3H3/t13-,14-,15-,18-,20+,21-/m0/s1

Synthetic route

testosterone acetate (1045-69-8) → clostebol acetate (855-19-6)

Conditions	Yield
Stage #1: testosterone acetate With 3,3-dimethyldioxirane In acetone at 20℃; for 8h; Epoxidation; Stage #2: With Amberlyst 15; sodium chloride In acetone at 20℃; for 12h; Chlorination;	89%
With pyridine; sulfuryl dichloride for 1h; Product distribution; Ambient temperature; other steroids;
With pyridine; sulfuryl dichloride for 1h; Ambient temperature;
Multi-step reaction with 2 steps 1: N-chloro-succinimide, HN3 / CHCl3; 2-methyl-propan-2-ol 2: SiO2 / benzene View Scheme
Multi-step reaction with 2 steps 1: N-chloro-succinimide, HN3 / CHCl3; 2-methyl-propan-2-ol 2: SiO2 / benzene View Scheme

17β-acetoxy-4β,5β-epoxyandrostan-3-one (5012-85-1) → clostebol acetate (855-19-6)

Conditions	Yield
With hydrogenchloride; acetic acid

acetic anhydride (108-24-7) + 4-Cloro-3-(2'-cloro-etossi)-Δ3,5-androstadien-17β-olo-acetato → clostebol acetate (855-19-6)

Conditions	Yield
(i) H2SO4, MeOH, (ii) /BRN= 385737/, Py; Multistep reaction;

4β-Chlor-5β-azido-androstanol-17β-on-3-acetat (18586-71-5) → clostebol acetate (855-19-6)

Conditions	Yield
With silica gel In benzene

4β-Chlor-5α-azido-androstanol-17β-on-3-acetat → clostebol acetate (855-19-6)

Conditions	Yield
With silica gel In benzene

2α,4-Dichlor-testosteron-acetat (857-14-7) → clostebol acetate (855-19-6)

Conditions	Yield
With acetic acid; zinc In methanol

4-Cloro-Δ4-androsten-17β-ol-3-one acetato etilenchetale → clostebol acetate (855-19-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) POCl3, DMF, trichloroethene, (ii) NaOAc 2: (i) H2SO4, MeOH, (ii) /BRN= 385737/, Py View Scheme

17β-acetoxy-2α-chloro-androst-4-en-3-one (855-60-7) → clostebol acetate (855-19-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: SO2Cl2, Py 2: Zn, AcOH / methanol View Scheme

clostebol acetate (855-19-6) + acetic anhydride (108-24-7) → 3,17β-diacetoxy-4-chloro-androsta-3,5-diene (112551-54-9)

Conditions	Yield
With pyridine hydrochloride

clostebol acetate (855-19-6) + propionic acid anhydride (123-62-6) → 17β-acetoxy-4-chloro-3-propionyloxy-androsta-3,5-diene (114694-63-2)

Conditions	Yield
With pyridine hydrochloride

clostebol acetate (855-19-6) → C42H60Cl2O6 (131400-48-1) + 17β-acetoxy-4-chloro-androst-3-ene (131400-47-0, 131400-52-7)

Conditions	Yield
With acetic acid; zinc for 5.5h; Ambient temperature;	A 233 mg B 3.1 g

clostebol acetate (855-19-6) → 17β-acetoxy-4-chloro-androst-3-ene (131400-47-0, 131400-52-7)

Conditions	Yield
With acetic acid; zinc In water at 15℃; for 0.25h; ultrasonic irradiation; Yield given;

clostebol acetate (855-19-6) → 17β-acetoxy-4-chloroandrosta-4,6-diene-3-one (21589-92-4) + 17β-acetoxy-4-chloroandrosta-1,4-diene-3-one (62799-78-4)

Conditions	Yield
With toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 24h; Heating;	A 350 mg B 500 mg

clostebol acetate (855-19-6) → 17β-acetoxy-3α-hydroxy-4-chloroandrost-4-ene (117993-39-2) + 17β-acetoxy-3β-hydroxy-4-chloroandrost-4-ene (117993-40-5)

Conditions	Yield
With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran for 3h;	A 250 mg B 6.7 g

clostebol acetate (855-19-6) → 17β-acetoxy-4β-chloro-4,5-epoxy-5α-androstan-3-one (113324-62-2) + 17β-acetoxy-4α-chloro-4,5-epoxy-5β-androstan-3-one (118100-03-1)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol at 5℃; for 18h;	A n/a B 230 mg

clostebol acetate (855-19-6) → 3,4-Dicloro-Δ3,5-androstadien-17β-olo acetato

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate

clostebol acetate (855-19-6) → 6-dehydrotestosterone (3591-23-9, 3593-33-7, 4030-88-0, 4223-57-8, 2484-30-2)

Conditions	Yield
With sulfuric acid; dimethyl sulfoxide
Multi-step reaction with 2 steps 1: LiCl / dimethylformamide 2: aq. K2CO3 / methanol View Scheme

clostebol acetate (855-19-6) → 17β-acetoxy-5α-androstan-3,6-dione (25469-53-8)

Conditions	Yield
With sulfuric acid; dimethyl sulfoxide

clostebol acetate (855-19-6) → androsta-4,6-dien-17β-ol-3-one acetate (2352-19-4)

Conditions	Yield
With sulfuric acid; dimethyl sulfoxide
With lithium chloride In N,N-dimethyl-formamide

clostebol acetate (855-19-6) → 17beta-Acetoxyandrost-4-ene-3,6-dione (4594-27-8, 6726-17-6)

Conditions	Yield
With dimethyl sulfoxide at 150℃;

clostebol acetate (855-19-6) → 17β-acetoxy-4-chloroandrosta-1,4-diene-3-one (62799-78-4)

Conditions	Yield
With acetic anhydride; selenious acid In tert-Amyl alcohol

clostebol acetate (855-19-6) → 2α-Brom-4-chlor-testosteronacetat

Conditions	Yield
(i) (CO2Et)2, NaH, benzene, (ii) NBS, Py; Multistep reaction;

clostebol acetate (855-19-6) + acetic anhydride (108-24-7) → 2α,4-Dichlor-testosteron-acetat (857-14-7)

Conditions	Yield
(i) (CO2Et)2, NaH, benzene, (ii) N-chloro-succinimide, Py, (iii) /BRN= 385737/, Py; Multistep reaction;

clostebol acetate (855-19-6) → 4,17β-dihydroxy-4,6-androstadien-3-one (4721-70-4)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol

clostebol acetate (855-19-6) → 17β-acetoxy-3β-hydroxy-4-chloroandrost-4-ene (117993-40-5)

Conditions	Yield
With chromium chloride; sodium tetrahydroborate In methanol at 0℃; for 0.333333h;	910 mg

clostebol acetate (855-19-6) + (aminooxy)acetic acid hemihydrochloride (2921-14-4, 7776-18-3, 20295-82-3) → 3-carboxymethyl-oxime-clostebol acetate

Conditions	Yield
With pyridine In ethanol at 20℃;

clostebol acetate (855-19-6) → clostebol (1093-58-9)

Conditions	Yield
With hydrogenchloride In acetone at 75℃; for 15h;

clostebol acetate (855-19-6) → clostebol-17-hemisuccinate (3038-80-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1 N aq. HCl / acetone / 15 h / 75 °C 2: pyridine / 120 h / 20 °C View Scheme

clostebol acetate (855-19-6) → 3-carboxymethyl-oxime-4-chloro-androstenedione

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / ethanol / 20 °C 2: 2 N aq. HCl / 3 h / 80 °C 3: aq. CrO3; H2SO4 / acetone / 0.08 h / 0 °C View Scheme

clostebol acetate (855-19-6) → [(8R,9S,10R,13S,14S,17S)-4-Chloro-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-(3E)-ylideneaminooxy]-acetic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / ethanol / 20 °C 2: 2 N aq. HCl / 3 h / 80 °C View Scheme

Upstream product

• 1045-69-8 testosterone acetate 
• 108-24-7 acetic anhydride 
• 855-60-7 17β-acetoxy-2α-chloro-androst-4-en-3-one 
• 857-14-7 2α,4-Dichlor-testosteron-acetat 
• 18586-71-5 4β-Chlor-5β-azido-androstanol-17β-on-3-acetat 
• 5012-85-1 17β-acetoxy-4β,5β-epoxyandrostan-3-one 

Downstream Products

• 42224-78-2 17β-acetoxyandrost-1,4,6-trien-3-one 
• 2141-17-5 4-hydroxytestosterone 
• 1093-58-9 clostebol 
• 2352-19-4 androsta-4,6-dien-17β-ol-3-one acetate 
• 3591-23-9 6-dehydrotestosterone 

Relevant articles and documents

SYNTHESIS OF 2-ALPHA-HALO-4-EN-3-OXO-STEROIDS.

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Yttrium compounds: New catalysts for the regioselective acylative cleavage of epoxides

The use of Cp2YCl and YCl3 as effective catalysts for the regioselective acylative cleavage of epoxides, especially for the conversion of α,β- epoxyketones to α-chloroenones is described.

Concerning the addition of chlorazide and bromazide to 3-keto-delta-4-steroids

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