5220-49-5

Basic information

• Product Name: 3-AMINO-2-CYCLOHEXEN-1-ONE
• Synonyms: 1-Aminocyclohexene-3-one;3-Amino-2-cyclohexen-1-one, 98% (dry wt.), may cont. up to 5% water;3-Amino-2-cyclohexen-1-one, 99%,96%;3-aminocyclohexenone;1-Amino-3-oxocyclohex-1-ene;1-Amino-1-cydohexene-3-one;3-Amino-2-cyclohexen-1-one 99%;AKOS 91521
• CAS NO: 5220-49-5
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• EINECS: 226-014-9
• Product Categories: Carbonyl Compounds;Ketones;Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;pharmacetical;C3 to C6
• Mol File: 5220-49-5.mol
• Article Data: 41

Chemical Properties

• Melting Point: 129-133 °C(lit.)
• Boiling Point: 212.42 °C at 760 mmHg
• Flash Point: 82.269 °C
• Appearance: /
• Density: 1.091 g/cm³
• Vapor Pressure: 0.00263mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Solubility: soluble in Methanol
• PKA: 5.65±0.20(Predicted)
• BRN: 471354
• CAS DataBase Reference: 3-AMINO-2-CYCLOHEXEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-2-CYCLOHEXEN-1-ONE(5220-49-5)
• EPA Substance Registry System: 3-AMINO-2-CYCLOHEXEN-1-ONE(5220-49-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 4.6
• Hazardous Substances Data: 5220-49-5(Hazardous Substances Data)

Usage

Chemical Properties

Dark yellow crystal

Uses

3-Amino-2-cyclohexen-1-one was used in the synthesis of a series of 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitriles.

InChI:InChI=1/C6H9NO/c7-5-2-1-3-6(8)4-5/h7H,1-4H2/b7-5+

Synthetic route

1,3-cylohexanedione (504-02-9) → 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
With ammonium acetate; tetraethoxy orthosilicate In ethanol Heating;	98%
With ammonium acetate at 110℃; for 0.25h; Temperature;	93.6%
With potassium hydrogensulfate; ammonium acetate; silica gel at 20℃; for 0.5h;	92%

m-Hydroxyaniline (591-27-5) → 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 60℃; under 760.051 Torr; for 14h; Temperature; Time; Green chemistry;	94%

1,3-Cyclohexanedione (30182-67-3) → 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
With ammonium acetate; acetic acid In benzene for 0.3h; Heating;	85%
With ammonium acetate In benzene for 5h; Reflux;	31%

m-phenylenediamine (108-45-2) → 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
	80%
With potassium hydroxide; hydrogen; acetic acid; palladium In water

3-aminocyclohex-2-ene-1-one potassium salt (1609011-32-6) → 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
With acetic acid In water	65%

m-phenylenediamine (108-45-2) → acetate salt of 3-amino-2-cyclohexene-1-imine + 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
	A 55% B n/a
	A 39% B n/a

N-benzyl-3-amino-2-cyclohexen-1-one (41609-04-5) + dimethyl acetylenedicarboxylate (762-42-5) + 1-amino-3-methylbenzene (108-44-1) → 4-hydroxy-5-oxo-2-phenyl-1-m-tolyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester + 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
With tert.-butylhydroperoxide; copper diacetate In water at 30℃; for 12h; Reagent/catalyst;	A 55% B n/a

m-phenylenediamine (108-45-2) → phosphate salt of 3-amino-2-cyclohexene-1-imine + 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
With phosphoric acid; hydrogen	A 25% B n/a

m-Hydroxyaniline (591-27-5) + acetonitrile (75-05-8) → 3-(ethylamino)phenol (621-31-8) + 3-(ethylamino)-2-cyclohexen-1-one (23076-01-9) + 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 23h; Green chemistry;

2-chloro-4-fluoro-5-nitrophenol (84478-75-1) → 5-hydroxy-2-fluoroaniline (62257-16-3) + 3-amino-cyclohex-2-enone (5220-49-5) + 4-chloro-2-fluoro-5-hydroxyaniline (84478-72-8)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; sodium hydroxide In methanol at 20℃; for 3h;	A 8 %Chromat. B 37 %Chromat. C 7 %Chromat.

2-chloro-4-fluoro-5-nitrophenol (84478-75-1) → 5-hydroxy-2-fluoroaniline (62257-16-3) + 3-amino-cyclohex-2-enone (5220-49-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; sodium acetate In methanol at 20℃; for 3h;	A 87 %Chromat. B 10 %Chromat.

bis(2,4,6-trichlorophenyl)butylmalonate (77510-25-9) + 3-amino-cyclohex-2-enone (5220-49-5) → 3-n-butyl-4-hydroxy-7,8-dihydrochinolin-2,5(1H,6H)-dion (119022-17-2)

Conditions	Yield
at 240℃; for 0.5h;	98%

embelin (550-24-3) + 3-amino-cyclohex-2-enone (5220-49-5) + 3-Fluorobenzaldehyde (456-48-4) → 9-(3-fluorophenyl)-2-hydroxy-3-undecyl-6,7,9,10-tetrahydro-5H-acridine-1,4,8-trione (1448168-14-6)

Conditions	Yield
In ethanol at 150℃; for 0.25h; Microwave irradiation;	98%

indan-1,2,3-trione hydrate (485-47-2) + 3-amino-cyclohex-2-enone (5220-49-5) → 4b,9b-dihydroxy-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione (1158819-69-2)

Conditions	Yield
at 20℃;	96%
With LACTIC ACID In neat (no solvent) at 20℃; for 0.166667h;	84%
at 20℃;
In methanol at 20℃; for 22h;

embelin (550-24-3) + benzaldehyde (100-52-7) + 3-amino-cyclohex-2-enone (5220-49-5) → 9-phenyl-2-hydroxy-3-undecyl-6,7,9,10-tetrahydro-5H-acridine-1,4,8-trione (1448168-18-0)

Conditions	Yield
In ethanol at 150℃; for 0.25h;	96%

1-Phenyl-4,4,4-trifluorobutane-1,3-dione (326-06-7) + 3-amino-cyclohex-2-enone (5220-49-5) → C16H12F3NO

Conditions	Yield
In acetic acid for 7h; Reflux; regioselective reaction;	96%

3-amino-cyclohex-2-enone (5220-49-5) + acrylic acid (79-10-7) → 3,4,7,8-tetrahydro-2,5(1H,6H)-quinolinequinone (5057-12-5)

Conditions	Yield
at 140℃; for 3h;	95%
for 6h; Reflux;	90.2%
In methanol	45.1%

methanol (67-56-1) + 3-amino-cyclohex-2-enone (5220-49-5) + acrolein (107-02-8) → 2-methoxy-2,3,4,6,7,8-hexahydro-1H-quinolin-5-one (98218-71-4)

Conditions	Yield
	95%
for 6h; Heating;	91%

3-nitrobenzylidenemalononitrile (2826-32-6) + 3-amino-cyclohex-2-enone (5220-49-5) → C16H12N4O3

Conditions	Yield
In propan-1-ol for 4h; Heating;	95%

4-fluorobenzylidenemalononitrile (2826-22-4) + 3-amino-cyclohex-2-enone (5220-49-5) → C16H12FN3O

Conditions	Yield
In propan-1-ol for 4h; Heating;	94%

formaldehyd (50-00-0) + 4-hydroxy-1-methyl-2(1H)-quinolone (1677-46-9) + 3-amino-cyclohex-2-enone (5220-49-5) → 3-[(2-amino-6-oxocyclohex-1-en-1-yl)methyl]-4-hydroxy-1-methyl-1,2-dihydroquinolin-2(1H)-one

Conditions	Yield
In neat (no solvent) at 100℃; for 0.166667h; Green chemistry;	94%

heptanal (111-71-7) + embelin (550-24-3) + 3-amino-cyclohex-2-enone (5220-49-5) → 9-hexyl-2-hydroxy-3-undecyl-6,7-dihydroacridine-1,4,8-(5H,8H,10H)-trione (1448168-21-5)

Conditions	Yield
In ethanol at 150℃; for 0.25h; Microwave irradiation;	93%

4-chlorobenzaldehyde (104-88-1) + 3-amino-cyclohex-2-enone (5220-49-5) + malononitrile (109-77-3) → 2-amino-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

Conditions	Yield
With zinc(II) oxide In ethanol at 80℃; for 0.5h; Sonication; Green chemistry;	93%
With iron oxide In ethanol for 0.2h; Reflux; Green chemistry;	92%
With magnesia In ethanol for 0.366667h; Reflux;	91%
With C12H24O6*C6H4NO5S(1-)*Na(1+) In ethanol for 0.25h; Reflux;	90%

3-amino-cyclohex-2-enone (5220-49-5) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-(4α-N,N-dimethylaminomethylene)amino-2-cyclohexen-1-one (727654-69-5)

Conditions	Yield
Stage #1: 3-amino-cyclohex-2-enone; N,N-dimethyl-formamide dimethyl acetal In tetrahydrofuran for 2.5h; Heating; Stage #2: In toluene for 1h; Heating; Further stages.;	92%

4-chlorobenzylidenemalonodinitrile (1867-38-5) + 3-amino-cyclohex-2-enone (5220-49-5) → C16H12ClN3O

Conditions	Yield
In propan-1-ol for 4h; Heating;	92%

4-hydroxy-1-methyl-2(1H)-quinolone (1677-46-9) + benzaldehyde (100-52-7) + 3-amino-cyclohex-2-enone (5220-49-5) → C23H22N2O3

Conditions	Yield
In neat (no solvent) at 100℃; for 0.333333h; Green chemistry;	92%

4-hydroxy-1-methyl-2(1H)-quinolone (1677-46-9) + 3-amino-cyclohex-2-enone (5220-49-5) + 4-methoxy-benzaldehyde (123-11-5) → C24H24N2O4

Conditions	Yield
In neat (no solvent) at 100℃; for 0.5h; Green chemistry;	92%

benzaldehyde (100-52-7) + 3-amino-cyclohex-2-enone (5220-49-5) + malononitrile (109-77-3) → 2-amino-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

Conditions	Yield
With zinc(II) oxide In ethanol at 80℃; for 0.533333h; Sonication; Green chemistry;	92%
With iron oxide In ethanol for 0.25h; Reflux; Green chemistry;	90%
With magnesia In ethanol for 0.4h; Reflux;	88%
With C12H24O6*C6H4NO5S(1-)*Na(1+) In ethanol for 0.3h; Reflux;	87%

1H-indene-1,3(2H)-dione (606-23-5) + N-propylisatin (41042-12-0) + 3-amino-cyclohex-2-enone (5220-49-5) → C26H22N2O3

Conditions	Yield
With acetic acid In ethanol for 12h; Reflux;	91.5%

1H-indene-1,3(2H)-dione (606-23-5) + 1-(2-Chloroethyl)isatin (77218-99-6) + 3-amino-cyclohex-2-enone (5220-49-5) → C25H19ClN2O3

Conditions	Yield
With acetic acid In ethanol for 12h; Reflux;	91.5%

4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione (893-33-4) + 3-amino-cyclohex-2-enone (5220-49-5) → C20H14F3NO

Conditions	Yield
In acetic acid for 7h; Reflux; regioselective reaction;	91%

3-amino-cyclohex-2-enone (5220-49-5) + 3-ethoxycarbonyltriazolo<1,5-a>pyridine (87838-54-8) → ethyl 2-((3-oxocyclohex-1-en-1-yl)amino)-2-(pyridin-2-yl)acetate

Conditions	Yield
With bis[rhodium(α,α,α',α'-tetramethyl-1,3-benzenedipropionic acid)] In 1,2-dichloro-ethane at 120℃; Inert atmosphere; Schlenk technique; Glovebox;	91%

1H-indene-1,3(2H)-dione (606-23-5) + N-butylisatin (4290-91-9) + 3-amino-cyclohex-2-enone (5220-49-5) → C27H24N2O3

Conditions	Yield
With acetic acid In ethanol for 12h; Reflux;	90.6%

3-amino-cyclohex-2-enone (5220-49-5) + diethyl 2-ethoxymethylenemalonate (87-13-8) → 2-[(3-oxocyclohex-1-enylamino)methylene]malonic acid diethyl ester (72912-99-3)

Conditions	Yield
	90%
at 130℃; for 4h;	90%
at 130℃; for 4h;	49%

4-Nitrobenzylidenemalononitrile (2700-23-4) + 3-amino-cyclohex-2-enone (5220-49-5) → C16H12N4O3

Conditions	Yield
In propan-1-ol for 4h; Heating;	90%

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 84478-75-1 2-chloro-4-fluoro-5-nitrophenol 
• 41609-04-5 N-benzyl-3-amino-2-cyclohexen-1-one 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 108-44-1 1-amino-3-methylbenzene 
• 108-45-2 m-phenylenediamine 
• 30182-67-3 1,3-Cyclohexanedione 
• 1609011-32-6 3-aminocyclohex-2-ene-1-one potassium salt 
• 591-27-5 m-Hydroxyaniline 
• 75-05-8 acetonitrile 

Downstream Products

• 56798-21-1 3,4,5,6-tetrahydroacridine-1,8(2H,7H)-dione 
• 143261-86-3 3-phenyl-7,8-dihydroquinoline-2,5(1H,6H)-dione 
• 143261-87-4 2-amino-3-phenyl-7,8-dihydroquinolin-5(6H)-one 
• 106960-78-5 5-Oxo-5,6,7,8-tetrahydro-quinoline-3-carboxylic acid ethyl ester 
• 130865-94-0 N¹-(3-oxocyclohex-1-enyl)-N²-phenylthiourea 
• 78831-30-8 4-oxo-1,2,3,4-tetrahydro-6-hydroxy<1>benzopyrano<3,4-b>quinoline 
• 27463-92-9 5,6,7,8-Tetrahydro-2-methylquinolin-5-one 
• 87883-18-9 3-nitro-5,6,7,8-tetrahydroquinolin-5-one 
• 143261-89-6 2,2-dimethyl-8,9-dihydro-1,3-dioxino<4,5-b>quinoline-4,6-dione 
• 143261-88-5 2,2-dimethyl-5-(3-oxo-1-cyclohexen-1-yl)aminomethylene-1,3-dioxane-4,6-dione 
• 69585-88-2 2-Allyl-3-amino-cyclohex-2-enone 
• 130865-95-1 N¹-(3-oxocyclohex-1-enyl)-N²-methylthiourea 
• 14006-77-0 2-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one 
• 5057-12-5 3,4,7,8-tetrahydro-2,5(1H,6H)-quinolinequinone 

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