65-06-5

Basic information

• Product Name: 1-Testosterone
• Synonyms: 1-TESTOSTERONE;1,(5-ALPHA)-ANDROSTEN-17-BETA-OL-3-ONE;1-DEHYDROANDROSTANOLONE;5Alpha-Androst-1-En-3-One-17-Ol;1-TestosteroneSeries;17b-Hydroxy-5a-androst-1-en-3-one;Androstendolone;(5S,8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS NO: 65-06-5
• Molecular Formula: C₁₉H₂₈O₂
• Molecular Weight: 288.42
• EINECS: 200-533-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Steroid and Hormone
• Mol File: 65-06-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 157-159?C
• Boiling Point: 120°C 0,5mm
• Flash Point: 179.5oC
• Appearance: /
• Density: 1.1561
• Vapor Pressure: 7.84E-09mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Controlled Substance, -20?C Freezer
• PKA: 15.08±0.60(Predicted)
• CAS DataBase Reference: 1-Testosterone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Testosterone(65-06-5)
• EPA Substance Registry System: 1-Testosterone(65-06-5)

Safety Data

• Hazardous Substances Data: 65-06-5(Hazardous Substances Data)

Usage

Description

1-Testosterone (Item No. 24079) is an analytical reference standard categorized as an anabolic androgenic steroid. Anabolic steroids, including 1-testosterone, have been used to enhance physical performance in racehorses and athletes. 1-Testosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

Chemical Properties

White Solid

Uses

1-Testosterone is a potent androgen with anabolic properties. Since the begining of the year 2005, the use of steroid precursors (prohormones) is illegal in the United States.

InChI:InChI=1/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,12,14-17,21H,3-6,8,10-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1

Synthetic route

(5α,17β)-3-oxoandrost-1-en-17-yl acetate (64-82-4, 6656-41-3, 21507-42-6, 25615-33-2, 54631-35-5, 79732-37-9, 97413-69-9) → 1-testosterone (65-06-5)

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 2h;	99.8%

5α-androst-1-en-3-one-17β-yl benzoate (1971-67-1) → 1-testosterone (65-06-5)

Conditions	Yield
With sodium hydroxide for 2h; Heating;	82.6%

17β-cyclohexanecarbonyloxy-5α-androst-1-en-3-one (119572-14-4) → 1-testosterone (65-06-5)

Conditions	Yield
With potassium hydroxide

5α-androst-1-ene-3α,17β-diol (38859-38-0) → 1-testosterone (65-06-5)

Conditions	Yield
With manganese(IV) oxide In dichloromethane

2-((3S,5S,8R,9S,10R,13S,14S,17S)-3,17-Dihydroxy-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-yl)-N,N-dimethyl-acetamide (63109-26-2) → 1-testosterone (65-06-5)

Conditions	Yield
at 250℃;

17β-acetoxy-5α-androsten-(1)-one-(3) → 1-testosterone (65-06-5)

Conditions	Yield
With potassium hydroxide

17β-acetoxy-2-bromo-5α-androstan-3-one (952222-37-6) → 1-testosterone (65-06-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99.6 percent / lithium bromide; lithium carbonate / dimethylformamide / 0.5 h / Heating 2: 99.8 percent / sodium hydroxide / methanol / 2 h / 20 °C View Scheme

stanolone acetate (1164-91-6) → 1-testosterone (65-06-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / hydrogen chloride; bromine / acetic acid / 1 h / 20 - 25 °C 2: 99.6 percent / lithium bromide; lithium carbonate / dimethylformamide / 0.5 h / Heating 3: 99.8 percent / sodium hydroxide / methanol / 2 h / 20 °C View Scheme

stanolone benzoate (1057-07-4) → 1-testosterone (65-06-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 5.1 g / Br2 / acetic acid / 3 h / Ambient temperature 2: CaCO3 / N,N-dimethyl-acetamide / 0.33 h / Heating 3: 82.6 percent / 5percent methanolic NaOH / 2 h / Heating View Scheme

2α-Brom-17β-benzoyloxy-5α-androstanon-(3) (96192-10-8) → 1-testosterone (65-06-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: CaCO3 / N,N-dimethyl-acetamide / 0.33 h / Heating 2: 82.6 percent / 5percent methanolic NaOH / 2 h / Heating View Scheme

2-bromo-17β-cyclohexanecarbonyloxy-5α-androst-1-en-3-one (119598-48-0) → 1-testosterone (65-06-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc-powder; ethanol 2: methanol.KOH View Scheme

2α,3α-epoxy-5α-androstan-17β-ol (965-66-2) → 1-testosterone (65-06-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: LDA, AcNMe2 / tetrahydrofuran 2: MnO2 / CH2Cl2 View Scheme

1-testosterone (65-06-5) + methyl chloroformate (79-22-1) → 17-β-methoxycarbonyloxy-5α-androst-1-en-3-one

Conditions	Yield
In pyridine at 0℃; for 24h;	90%

1-testosterone (65-06-5) → 5α-androst-1-ene-3,17-dione (571-40-4)

Conditions	Yield
With chromium(VI) oxide In water; acetic acid at 25 - 30℃; for 1h;	88.9%

1-testosterone (65-06-5) + bis-(2-methyl-1H-imidazol-1-yl)methanone (13551-83-2) → 3-oxo-5α-androst-1-en-17β-yl-2'-methyl-1H-imidazole-1-carboxylate (1138159-99-5)

Conditions	Yield
In dichloromethane for 5h; Heating;	84%

1-testosterone (65-06-5) → 5α-androst-1β,2β-epoxude-3-on-17β-ol (135415-79-1)

Conditions	Yield
With tert.-butylhydroperoxide; hexacarbonyl molybdenum In dichloromethane Heating;	69.9%

1-testosterone (65-06-5) + N-hydroxy-4-methoxy-benzenecarboximidoyl chloride (38435-51-7) → C27H35NO4 (1620964-84-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 5h; Reflux;	66%

1-testosterone (65-06-5) + N-hydroxy-2-methylbenzenecarboximidoyl chloride (74467-03-1) → C27H35NO3 (1620964-85-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 5h; Reflux;	62%

1-testosterone (65-06-5) + N-hydroxy-4-methylbenzenecarboximidoyl chloride (36288-37-6) → C27H35NO3 (1620964-87-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 5h; Reflux;	53%

1-testosterone (65-06-5) + 3-methyl-N-hydroxy-benzenecarboximidoyl chloride (61946-92-7) → C27H35NO3 (1620964-86-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 5h; Reflux;	51%

1-testosterone (65-06-5) + benzohydroximoyl chloride (698-16-8) → C26H33NO3 (1620964-70-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 5h; Reflux;	44%

1-testosterone (65-06-5) + 4-chlorobenzohydroximoyl chloride (28123-63-9) → C26H32ClNO3 (1620964-88-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 5h; Reflux;	37%

ethanol (64-17-5) + 1-testosterone (65-06-5) → 5-androgen-3,17-diol (571-20-0)

Conditions	Yield
Behandeln mit gaerender Hefe;

1-testosterone (65-06-5) → 1α,2α-epoxy-5α-androstan-17β-ol-3-one (13093-66-8)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

1-testosterone (65-06-5) → 3-trichloromethyl-5α-androst-1-ene-3ξ,17β-diol (110875-13-3)

Conditions	Yield
With tetrahydrofuran; chloroform; potassium tert-butylate Reagens 4: tert-Butylalkohol;

1-testosterone (65-06-5) + acetic anhydride (108-24-7) → syn-17β-Acetoxy-5α-Δ1-androsten-3-N-chlorimin + anti-17β-Acetoxy-5α-Δ1-androsten-3-N-chlorimin

Conditions	Yield
(i) cyclohexylamine, toluene, (ii) NH2Cl, NH3, MeOH, Et2O, (iii) /BRN= 385737/, Py; Multistep reaction;

1-methoxy-cyclohex-1-ene (931-57-7) + 1-testosterone (65-06-5) → mesabolone (7483-09-2)

Conditions	Yield
With pyridine; toluene-4-sulfonic acid In tert-butyl alcohol

1-methoxycyclopentene (1072-59-9) + 1-testosterone (65-06-5) → (5S,8R,9S,10R,13S,14S,17S)-17-(1-Methoxy-cyclopentyloxy)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

Conditions	Yield
With pyridine; toluene-4-sulfonic acid In tert-butyl alcohol

1-testosterone (65-06-5) + benzoyl chloride (98-88-4) → 5α-androst-1-en-3-one-17β-yl benzoate (1971-67-1)

Conditions	Yield
With pyridine

1-testosterone (65-06-5) + Methyltriphenylphosphonium bromide (1779-49-3) → 3-Methylen-5α-androst-1-en-17β-ol (2857-40-1)

Conditions	Yield
(i) nBuLi, (ii) /BRN= 2220746/; Multistep reaction;

Vinyl bromide (593-60-2) + 1-testosterone (65-06-5) → 17β-Hydroxy-1α-vinyl-5α-androstan-3-on (57177-39-6)

Conditions	Yield
(i) Mg, THF, (ii) /BRN= 2220746/, Cu(OAc)2; Multistep reaction;

N,N-dimethyl acetamide (127-19-5) + 1-testosterone (65-06-5) → 2-((3S,5S,8R,9S,10R,13S,14S,17S)-3,17-Dihydroxy-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-yl)-N,N-dimethyl-acetamide (63109-26-2)

Conditions	Yield
(i) LDA, THF, (ii) /BRN= 2220746/; Multistep reaction;

1,1-diethoxycyclohexane (1670-47-9) + 1-testosterone (65-06-5) → (5S,8R,9S,10R,13S,14S,17S)-17-(Cyclohex-1-enyloxy)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

Conditions	Yield
With toluene-4-sulfonic acid In benzene

1,1-diethoxy-cyclopentane (23786-93-8) + 1-testosterone (65-06-5) → 5α-Androst-1-en-17β-ol-3-on-17- (7207-85-4)

Conditions	Yield
at 140 - 190℃;

1-testosterone (65-06-5) + ethylmagnesium bromide (925-90-6) → 17β-Hydroxy-1α-aethyl-5α-androstanon-(3) (4133-37-3)

Conditions	Yield
With copper diacetate In tetrahydrofuran

1-testosterone (65-06-5) → 2-chloro-17β-hydroxy-5α-androst-1-en-3-one (5902-35-2)

Conditions	Yield
(i) aq. H2O2, NaOH, MeOH, (ii) aq. HCl, acetone; Multistep reaction;

Upstream product

• 965-66-2 2α,3α-epoxy-5α-androstan-17β-ol 
• 119598-48-0 2-bromo-17β-cyclohexanecarbonyloxy-5α-androst-1-en-3-one 
• 96192-10-8 2α-Brom-17β-benzoyloxy-5α-androstanon-(3) 
• 1057-07-4 stanolone benzoate 
• 1164-91-6 stanolone acetate 
• 952222-37-6 (5S,8R,9S,10S,13S,14S,17S)-2-bromo-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate 
• 64-82-4 (5α,17β)-3-oxoandrost-1-en-17-yl acetate 
• 63109-26-2 2-((3S,5S,8R,9S,10R,13S,14S,17S)-3,17-Dihydroxy-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-yl)-N,N-dimethyl-acetamide 
• 38859-38-0 5α-androst-1-ene-3α,17β-diol 
• 1971-67-1 5α-androst-1-en-3-one-17β-yl benzoate 
• 119572-14-4 17β-cyclohexanecarbonyloxy-5α-androst-1-en-3-one 
• 521-18-6 dihydrotestosterone 

Downstream Products

• 1620964-88-6 C₂₆H₃₂ClNO₃ 
• 1620964-87-5 C₂₇H₃₅NO₃ 
• 1620964-86-4 C₂₇H₃₅NO₃ 
• 1620964-85-3 C₂₇H₃₅NO₃ 
• 1620964-84-2 C₂₇H₃₅NO₄ 
• 1620964-70-6 C₂₆H₃₃NO₃ 
• 1971-67-1 5α-androst-1-en-3-one-17β-yl benzoate 
• 7483-09-2 mesabolone 
• 86306-64-1 17-β-methoxycarbonyloxy-5α-androst-1-en-3-one 
• 571-40-4 5α-androst-1-ene-3,17-dione 
• 571-20-0 5-androgen-3,17-diol 

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