Aminoglutethimide supplier

Name
Aminoglutethimide
EINECS 204-756-4
CAS No. 125-84-8
Article Data9
CAS DataBase
Density 1.173 g/cm³
Solubility slightly soluble in water
Melting Point 152-154 °C(lit.)
Formula C₁₃H₁₆N₂O₂
Boiling Point 457.4 °C at 760 mmHg
Molecular Weight 232.282
Flash Point 230.4 °C
Transport Information UN 3249
Appearance white solid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Glutarimide,2-(p-aminophenyl)-2-ethyl- (6CI,7CI,8CI);(RS)-Aminoglutethimide;3-(4-Aminophenyl)-3-ethylpiperidine-2,6-dione;Ba-16038;Cytadren;DL-Aminoglutethimide;Elipten;NSC 330915;Orimeten;p-Aminoglutethimide;
PSA 72.19000
LogP 2.26320

Synthetic route

: dimethyl 2-(1-((4-(3-ethyl-2,6-dioxopiperidin-3-yl)phenyl)amino)hex-5-yn-1-ylidene)malonate

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
With acetic acid at 20℃; for 1h;	99%

: 38527-73-0
rac-3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 1h;	95%
With hydrogen; palladium on activated charcoal In ethanol	91%
With hydrogen; palladium on activated charcoal In methanol for 5h; Ambient temperature;	90%

: 183663-77-6
1-hydroxy-3-ethyl-3-(4-aminophenyl)piperidine-2,6-dione

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
With dmap; triethylamine; α-bromoacetophenone In acetonitrile for 24h; Ambient temperature;

(+-)-3-ethyl-3-<4-nitro-phenyl>-piperidine-2,6-dione: (+-)-3-ethyl-3-<4-nitro-phenyl>-piperidine-2,6-dione

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
With nickel; ethyl acetate Hydrogenation;

: 2-Ethyl-2-(4-nitro-phenyl)-pentanedioic acid

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / trifluoroacetamide, 1-hydroxybenzotriazole, triethylamine, N-(3-dimethylamino)propyl-N-ethylcarbodiimide hydrochloride / 1 h / Ambient temperature 2: 95 percent / H2 / Pd/C / ethanol / 1 h / 760 Torr View Scheme
Multi-step reaction with 3 steps 1: 81 percent / N-ethyl-N-dimethylaminopropylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, triethylamine / CH2Cl2 / 0 °C 2: 10percent Pd/C, H2 / methanol / 2 h 3: triethylamine, bromoacetophenone, DMAP / acetonitrile / 24 h / Ambient temperature View Scheme

: 6973-78-0
2-(4-Nitrophenyl)-buttersaeureethylester

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) NaH / 1) DMF, 0 deg C, 60 min, 2) DMF, 0 deg C, 0.5 h 2: 60 percent / polyphosphoric acid / 0.5 h / 180 °C 3: 90 percent / H2 / Pd/C / methanol / 5 h / Ambient temperature View Scheme

: 98-95-3
nitrobenzene

ammonium sulfite: ammonium sulfite

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 58 percent / NaH / dimethylformamide / 2 h / 0 °C 2: 1) NaH / 1) DMF, 0 deg C, 60 min, 2) DMF, 0 deg C, 0.5 h 3: 60 percent / polyphosphoric acid / 0.5 h / 180 °C 4: 90 percent / H2 / Pd/C / methanol / 5 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 65 percent / NaH / dimethylformamide / 2.5 h / 0 °C 2: 1) NaH / 1) DMF, 0 deg C, 60 min, 2) DMF, 0 deg C, 0.5 h 3: 60 percent / polyphosphoric acid / 0.5 h / 180 °C 4: 90 percent / H2 / Pd/C / methanol / 5 h / Ambient temperature View Scheme

: 203808-68-8
4-(ethoxycarbonyl)-4-(4'-nitrophenyl)hexanonitrile

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / polyphosphoric acid / 0.5 h / 180 °C 2: 90 percent / H2 / Pd/C / methanol / 5 h / Ambient temperature View Scheme

: 183663-75-4
1-benzyloxy-3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 10percent Pd/C, H2 / methanol / 2 h 2: triethylamine, bromoacetophenone, DMAP / acetonitrile / 24 h / Ambient temperature View Scheme

: 74220-50-1
2-ethyl-2-phenylglutarodinitrile

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 59 percent / concd H2SO4, CH3CO2H / 6 h 2: 9 percent / concd H2SO4, 63percent aq. HNO3 / 2 h / -10 - 0 °C 3: 91 percent / H2 / 10percent Pd/C / ethanol View Scheme

: 769-68-6
2-phenylbutanenitrile

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 53 percent / trimethylbenzylammoniumhydroxide (Triton B) / dioxane; methanol / 15 h / Heating 2: 59 percent / concd H2SO4, CH3CO2H / 6 h 3: 9 percent / concd H2SO4, 63percent aq. HNO3 / 2 h / -10 - 0 °C 4: 91 percent / H2 / 10percent Pd/C / ethanol View Scheme

: 140-29-4
phenylacetonitrile

phenylcyanopyruvic acid ethyl ester-phenylhydrazone of mp: 107-108 degree: phenylcyanopyruvic acid ethyl ester-phenylhydrazone of mp: 107-108 degree

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 73 percent / NaNH2 / benzene; toluene / 1 h / 80 °C 2: 53 percent / trimethylbenzylammoniumhydroxide (Triton B) / dioxane; methanol / 15 h / Heating 3: 59 percent / concd H2SO4, CH3CO2H / 6 h 4: 9 percent / concd H2SO4, 63percent aq. HNO3 / 2 h / -10 - 0 °C 5: 91 percent / H2 / 10percent Pd/C / ethanol View Scheme

: 77-21-4, 17575-58-5, 17575-59-6, 18389-24-7
Glutethimide

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 9 percent / concd H2SO4, 63percent aq. HNO3 / 2 h / -10 - 0 °C 2: 91 percent / H2 / 10percent Pd/C / ethanol View Scheme

: N-(4-(3-ethyl-2,6-dioxopiperidin-3-yl)phenyl)hex-5-ynethioamide

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 12 h / 20 °C 2: acetic acid / 1 h / 20 °C View Scheme

: C19H22N2O3

: 125-84-8
aminoglutethimide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 0.5 h / 20 °C / Molecular sieve 1.2: 2 h / 0 °C / Molecular sieve 2.1: methanol / 12 h / 20 °C 3.1: acetic acid / 1 h / 20 °C View Scheme

: 125-84-8
aminoglutethimide

: C13H14(2)H2N2O2

Conditions

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 21h; Inert atmosphere;	100%
With water-d2 In tetrahydrofuran at 80℃; under 760.051 Torr; for 3h; Sealed tube;	82%

: 125-84-8
aminoglutethimide

: C13H14N4O2

Conditions

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;	99%

: 125-84-8
aminoglutethimide

: 3282-30-2
pivaloyl chloride

: N-(4-(3-ethyl-2,6-dioxopiperidin-3-yl)phenyl)pivalamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	98%

: 81-08-3
2-sulfobenzoic acid cyclic anhydride

: 125-84-8
aminoglutethimide

: 2-[4-(3-Ethyl-2,6-dioxo-piperidin-3-yl)-phenylsulfamoyl]-benzoic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile for 2h; Heating;	93%

: 125-84-8
aminoglutethimide

: 67393-83-3, 67393-84-4, 67663-02-9, 91603-21-3, 91603-22-4, 118759-60-7, 118759-61-8
2-((2RS,3RS)-3-ethyloxiran-2-yl)ethan-1-ol

: C19H28N2O4

Conditions

Conditions	Yield
With 3,4,5-trifluorophenylboronic acid at 60℃; for 24h; regioselective reaction;	91%

: tetrafluoroboric acid

: 125-84-8
aminoglutethimide

: 7632-00-0
sodium nitrite

: 4‐(3‐ethyl‐2,6‐dioxopiperidin‐3‐yl)benzene‐1‐diazonium tetrafluoroborate

Conditions

Conditions	Yield
In water at 0℃; for 0.75h; Inert atmosphere;	90%

...Expand

: 125-84-8
aminoglutethimide

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

: N-{4-[4-(3-Ethyl-2,6-dioxo-piperidin-3-yl)-phenylsulfamoyl]-phenyl}-acetamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 40℃; for 4h;	89%

: 125-84-8
aminoglutethimide

: 68460-01-5
2,3,4,5-tetrabromo-6-sulfo-benzoic acid-anhydride

: 2,3,4,5-Tetrabromo-6-[4-(3-ethyl-2,6-dioxo-piperidin-3-yl)-phenylsulfamoyl]-benzoic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile for 2h; Heating;	88%

: 85-44-9
phthalic anhydride

: 125-84-8
aminoglutethimide

: 2-[4-(3-ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-isoindole-1,3-dione

Conditions

Conditions	Yield
With pyridine for 1h; Heating;	85.36%

: 125-84-8
aminoglutethimide

: 98-61-3
4-iodobenzenesulfonyl chloride

: N-[4-(3-Ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-4-iodo-benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 40℃; for 4h;	85%

: tetrafluoroboric acid

: 125-84-8
aminoglutethimide

: 4‐(3‐ethyl‐2,6‐dioxopiperidin‐3‐yl)benzene‐1‐diazonium tetrafluoroborate

Conditions

Conditions	Yield
With sodium nitrite In water at 0℃; for 0.5h;	84%

: 125-84-8
aminoglutethimide

: 5-methylene-4-phenyl-4-vinyl-1,3-dioxolan-2-one

: 3-ethyl-3-(4-(2-methyl-3-phenyl-1H-pyrrol-1-yl)phenyl)piperidine-2,6-dione

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; trifuran-2-yl-phosphane In dichloromethane at 20℃; for 12h;	83%

: 125-84-8
aminoglutethimide

: 832-53-1
pentafluorobenzenesulonyl chloride

: N-[4-(3-Ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-2,3,4,5,6-pentafluoro-benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 40℃; for 4h;	82%

: 125-84-8
aminoglutethimide

: C14H11ClN6S

: C28H27N7O2S

Conditions

Conditions	Yield
In ethanol at 20℃;	82%

: 125-84-8
aminoglutethimide

: C14H11ClN6S

: C27H26N8O2S

Conditions

Conditions	Yield
In ethanol at 20℃;	82%

: 125-84-8
aminoglutethimide

: 388628-24-8
1-[(dimethylamino)methylene]-1,3-dihydro-2H-pyrrolol[3,2-f]quinolin-2-one

: 297756-95-7
3-ethyl-3-(4-{(Z)-[(2-oxo-2,3-dihydro-1H-pyrrolo[3,2-f]quinolin-1-ylidene)methyl]amino}phenyl)-2,6-piperidinedione

Conditions

Conditions	Yield
	81%

: 125-84-8
aminoglutethimide

: 333-27-7
methyl trifluoromethanesulfonate

: 4-(3-ethyl-2,6-dioxopiperidin-3-yl)-N,N,N-trimethylbenzenaminium trifluoromethanesulfonate

Conditions

Conditions	Yield
With sodium carbonate In acetonitrile at 20℃; for 2h;	80%

: 95794-28-8
ethyl 3-bromomethyl-4-oxochromene-2-carboxylate

: 125-84-8
aminoglutethimide

: 2-[4-(3-Ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-1,2-dihydro-chromeno[2,3-c]pyrrole-3,9-dione

Conditions

Conditions	Yield
In ethanol for 4h; Heating;	78%

: 125-84-8
aminoglutethimide

: 3044-70-0
2,6-dimethyl-4-phenyl-pyrylium; perchlorate

: 1-<4-(2-ethyl-2-glutarimido)-phenyl>-2,6-dimethyl-4-phenylpyridinium perchlorate

Conditions

Conditions	Yield
In methanol for 2h; Heating;	78%

: 125-84-8
aminoglutethimide

: 1484-88-4
2,4,6-triphenylpyrilium perchlorate

: 1-<4-(2-ethyl-2-glutarimido)-phenyl>-2,4,6-triphenylpyridinium perchlorate

Conditions

Conditions	Yield
In methanol for 2h; Heating;	77%

: 4821-94-7
4,5-dimethoxyphthalic anhydride

: 125-84-8
aminoglutethimide

: 2-[4-(3-ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-5,6-dimethoxy-isoindole-1,3-dione

Conditions

Conditions	Yield
With pyridine for 1h; Heating;	76.96%

: 125-84-8
aminoglutethimide

: 2,6-di-t-butyl-4-methylpyrylium perchlorate

: 1-<4-(2-ethyl-2-glutarimido)-phenyl>-2,6-bis-tert-butyl-4-methylpyridinium perchlorate

Conditions

Conditions	Yield
In methanol for 2h; Heating;	76%

: 125-84-8
aminoglutethimide

: 98-60-2
4-chlorobenzenesulfonyl chloride

: 4-Chloro-N-[4-(3-ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-benzenesulfonamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 40℃; for 4h;	76%

: 125-84-8
aminoglutethimide

: ((2S*,3R*)-3-propyl-1-tosylaziridin-2-yl)methanol

: C26H35N3O5S

Conditions

Conditions	Yield
With zinc trifluoromethanesulfonate In ethyl acetate at 70℃; for 12h; regioselective reaction;	76%

: 125-84-8
aminoglutethimide

: 142-62-1
hexanoic acid

: 3-ethyl-3-(4-(pentylamino)phenyl)piperidine-2,6-dione

Conditions

Conditions	Yield
With 9-(2-chlorophenyl)acridine; di-tert-butyl peroxide; copper(II) hexafluoroacetylacetonate In ethyl acetate at 35℃; for 36h; Inert atmosphere; Irradiation;	76%

: 5893-05-0
Trt-Gly

: 125-84-8
aminoglutethimide

: N-[4-(3-ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-2-(trityl-amino)-acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	75%

: 125-84-8
aminoglutethimide

: 141109-47-9
[di(propan-2-yl)amino](oxo)acetyl chloride

: N1-(4-(3-ethyl-2,6-dioxopiperidin-3-yl)phenyl)-N2,N2-diisopropyloxalamide

Conditions

Conditions	Yield
Stage #1: aminoglutethimide; [di(propan-2-yl)amino](oxo)acetyl chloride In dichloromethane at 0℃; for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 2h;	75%

Aminoglutethimide Specification

The Aminoglutethimide is an organic compound with the formula C₁₃H₁₆N₂O₂. The IUPAC name of this chemical is 3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione. With the CAS registry number 125-84-8, it is also named as 2,6-piperidinedione, 3-(4-aminophenyl)-3-ethyl-. The product's categories are Antitumors for Research and Experimental Use; Biochemistry; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a white solid, which should be stored in a closed palce at temperature of 2 - 8 °C. It is used as an aromatase inhibitor and blocks adrenal steroidogenesis.

Physical properties about Aminoglutethimide are: (1)ACD/LogP: 1.41; (2)ACD/LogD (pH 5.5): 1.38; (3)ACD/LogD (pH 7.4): 1.41; (4)ACD/BCF (pH 5.5): 6.54; (5)ACD/BCF (pH 7.4): 6.98; (6)ACD/KOC (pH 5.5): 130.94; (7)ACD/KOC (pH 7.4): 139.87; (8)#H bond acceptors: 4; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 40.62 Å²; (12)Index of Refraction: 1.566; (13)Molar Refractivity: 64.58 cm³; (14)Molar Volume: 197.9 cm³; (15)Polarizability: 25.6×10^-24cm³; (16)Surface Tension: 46.6 dyne/cm; (17)Density: 1.173 g/cm³; (18)Flash Point: 230.4 °C; (19)Enthalpy of Vaporization: 71.75 kJ/mol; (20)Boiling Point: 457.4 °C at 760 mmHg; (21)Vapour Pressure: 1.5E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by 3-ethyl-3-(4-nitro-phenyl)-piperidine-2,6-dione. This reaction will need reagent H₂, catalyst 10percent Pd/C and solvent ethanol. The yield is about 91%.

Uses of Aminoglutethimide: it can be used to produce o-iodoaminoglutethimide by heating. It will need reagent I₂/KI and solvent methanol, H₂O with reaction time of 30 min. The yield is about 70%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1NC(=O)CCC1(c2ccc(N)cc2)CC
(2)InChI: InChI=1/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)
(3)InChIKey: ROBVIMPUHSLWNV-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)
(5)Std. InChIKey: ROBVIMPUHSLWNV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	LDLo	oral	21mg/kg/3D-I (21mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Annals of Internal Medicine. Vol. 105, Pg. 633, 1986.
mouse	LD50	intraperitoneal	625mg/kg (625mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC	Journal of Medicinal Chemistry. Vol. 18, Pg. 736, 1975.
women	TDLo	oral	20500mg/kg/94 (20500mg/kg)	BLOOD: AGRANULOCYTOSIS	British Medical Journal. Vol. 291, Pg. 970, 1985.

Product Name

Aminoglutethimide

Synthetic route

Aminoglutethimide Specification

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