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

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

Uses

Used in Pharmaceutical Industry:
3-AMINO-2-CYCLOHEXEN-1-ONE is used as a synthetic intermediate for the development of novel pharmaceutical compounds. Its ability to be incorporated into complex molecular structures makes it a valuable asset in the design and synthesis of new drugs with potential therapeutic applications.
Used in Chemical Industry:
In the chemical industry, 3-AMINO-2-CYCLOHEXEN-1-ONE is used as a key building block for the synthesis of various organic compounds, including those with potential applications in materials science, agrochemicals, and other specialty chemicals. Its versatility in chemical reactions allows for the creation of a diverse range of products.
Used in Synthesis of 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitriles:
3-AMINO-2-CYCLOHEXEN-1-ONE is specifically used as a starting material in the synthesis of a series of 2-amino-5-oxo-4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitriles. These compounds have potential applications in various fields, such as pharmaceuticals, due to their unique chemical properties and structures.

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

Downstream Products

• 119022-15-0 4-hydroxy-3-phenyl-7,8-dihydrochinolin-2,5(1H,6H)-dion 
• 78831-09-1 7,8-dihydro-2-(2-hydroxyphenyl)-3-nitroquinol-5-(6H)one 
• 77903-18-5 3-methyl-1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione 
• 145801-81-6 Pent-4-enoic acid (3-oxo-cyclohex-1-enyl)-amide 
• 6116-87-6 2-methyl-3-phenyl-1,5,6,7-tetrahydro-indol-4-one 
• 113859-92-0 3-(1-Methyl-2-oxo-2-phenyl-ethylamino)-cyclohex-2-enone 
• 6116-85-4 3-methyl-2-phenyl-1,5,6,7-tetrahydro-indol-4-one 
• 113859-89-5 3-(2-Oxo-1-phenyl-propylamino)-cyclohex-2-enone 
• 107974-86-7 5-Oxo-2-phenylsulfanylmethyl-4-(2-trifluoromethyl-phenyl)-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester 
• 107974-87-8 (3R,4S)-5-Oxo-2-[1-phenylsulfanyl-meth-(E)-ylidene]-4-(2-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinoline-3-carboxylic acid ethyl ester 
• 107974-87-8 (3R,4S)-5-Oxo-2-[1-phenylsulfanyl-meth-(Z)-ylidene]-4-(2-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinoline-3-carboxylic acid ethyl ester 
• 114957-66-3 (3S,4R)-5-Oxo-2-[2-oxo-2-phenyl-eth-(Z)-ylidene]-4-(2-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinoline-3-carboxylic acid ethyl ester 
• 119022-16-1 3-benzyl-4-hydroxy-7,8-dihydrochinolin-2,5(1H,6H)-dion 
• 80960-21-0 Toluene-4-sulfonate(2-amino-6-oxo-cyclohex-1-enyl)-phenyl-iodonium; 

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