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Tropinone

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Name

Tropinone

EINECS 208-530-6
CAS No. 532-24-1 Density 1.066 g/cm3
PSA 20.31000 LogP 0.75000
Solubility Melting Point 40-44 °C(lit.)
Formula C8H13NO Boiling Point 217.1 °C at 760 mmHg
Molecular Weight 139.20 Flash Point 90 °C
Transport Information UN 1544 Appearance white to light yellow crystal powder
Safety 23-24/25-36/37/39-26-22 Risk Codes 34-22-36/37/38
Molecular Structure Molecular Structure of 532-24-1 (Tropinone) Hazard Symbols CorrosiveC, IrritantXi
Synonyms

1aH,5aH-Tropan-3-one(8CI);Tropanone (6CI);Tropinone (7CI);3-Tropanone;3-Tropinone;8-Methyl-8-azabicyclo[3.2.1]octan-3-one;N-Methyl-8-azabicyclo[3.2.1]octan-3-one;NSC 118012;

 

Tropinone Synthetic route

1192-93-4

cyclohepta-2,6-dienone

593-51-1

methylamine hydrochloride

532-24-1

tropinone

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 2h;72%
100371-46-8

3-oxo-tropane-2,4-dicarboxylic acid dimethyl ester

A

36127-17-0

(+/-)-2-(carbomethoxy)-3-tropinone

B

532-24-1

tropinone

Conditions
ConditionsYield
With phosphate buffer In water at 20℃; for 24h; pH=8.0; Decarboxylation; demethoxycarbonylation;A 55%
B 13%
45771-52-6

(+/-)-hygrine

A

532-24-1

tropinone

B

1-[1-Methyl-pyrrolidin-(2E)-ylidene]-propan-2-one

Conditions
ConditionsYield
With mercury(II) diacetate In acetic acid for 18h; Heating;A 12%
B 25%
542-05-2

acetonedicarboxylic acid

638-37-9

butanedial

593-51-1

methylamine hydrochloride

A

532-24-1

tropinone

B

36295-25-7

2-[1-methyl-5-(2-oxopropyl)pyrrolidin-2-yl]acetone

Conditions
ConditionsYield
With disodium hydrogenphosphate; water bei pH 6.8;
5690-89-1

(1-methyl-pyrrolidine-2,5-diyl)-di-acetic acid diethyl ester

532-24-1

tropinone

Conditions
ConditionsYield
With 4-methylisopropylbenzene; sodium at 160℃;
With xylene; sodium t-butanolate Erhitzen des jeweiligen Reaktionsprodukts mit wss. Schwefelsaeure oder Salzsaeure;
638-37-9

butanedial

67-64-1

acetone

74-89-5

methylamine

532-24-1

tropinone

Conditions
ConditionsYield
With water
638-37-9

butanedial

105-50-0

diethyl 1,3-acetonedicarboxylate

74-89-5

methylamine

532-24-1

tropinone

Conditions
ConditionsYield
Erhitzen der sauren Loesung des Reaktionsprodukts;
542-05-2

acetonedicarboxylic acid

638-37-9

butanedial

74-89-5

methylamine

532-24-1

tropinone

Conditions
ConditionsYield
in verduennter waessriger Loesung im pH-Bereich 3-11 bei ca. 3-taegiem Stehenlassen bei Raumtemperatur;
at 20 - 25℃; bei pH 3-11;
Conditions
ConditionsYield
elektrolytischen Oxydation in saurer oder swach alkalischer Loesung;
120-29-6

3-tropanol

532-24-1

tropinone

Conditions
ConditionsYield
With chromium(III) oxide; sulfuric acid at 0℃;
With chromic acid; acetic acid at 60 - 70℃;
With sulfuric acid; chromic acid at 50 - 55℃;
135-97-7

pseudotropine

532-24-1

tropinone

Conditions
ConditionsYield
With chromic acid; acetic acid at 60 - 70℃;
With sulfuric acid; permanganate(VII) ion at 10 - 12℃;
With lead dioxide at 60 - 70℃;
With potassium hexacyanoferrate(III)
With chromic acid; acetic acid at 60 - 70℃;
481-37-8

ecgonine

532-24-1

tropinone

Conditions
ConditionsYield
With sulfuric acid; chromic acid at 60℃; und anschliessendem Kochen mit Schwefelsaeure;
62251-43-8, 62251-46-1

2β-bromo-8-methyl-8-azabicyclo<3.2.1>octan-3-one

532-24-1

tropinone

Conditions
ConditionsYield
With K2CO3,H2/Ra Ni 28 In water under 3.3 Torr; for 0.5h;

3-nitroso-3-acetoxytropane

532-24-1

tropinone

Conditions
ConditionsYield
With sulfuric acid Ambient temperature; Yield given;
In dichloromethane Product distribution; Ambient temperature; also on treatment with dilute H2SO4;

2α-bromotropan-3-one

532-24-1

tropinone

Conditions
ConditionsYield
With K2CO3,H2/Ra Ni 28 In water under 3.3 Torr; for 0.5h;

3,6-Bis-benzenesulfonyl-cycloheptanone

74-89-5

methylamine

532-24-1

tropinone

Conditions
ConditionsYield
In methanol; water Yield given;
100055-81-0

3-oxo-tropane-2-carboxylic acid ethyl ester

7664-93-9

sulfuric acid

532-24-1

tropinone

638-37-9

butanedial

74-89-5

methylamine

acetone-α.α'-dicarboxylate calcium

acetone-α.α'-dicarboxylate calcium

532-24-1

tropinone

Conditions
ConditionsYield
Erhitzen der sauren Loesung des Reaktionsprodukts;
alkaline potassium ferricyanide solution

alkaline potassium ferricyanide solution

532-24-1

tropinone

64-19-7

acetic acid

chromic acid

chromic acid

532-24-1

tropinone

Conditions
ConditionsYield
at 60 - 70℃;
at 60 - 70℃;
Cr2O3-H2SO4

Cr2O3-H2SO4

532-24-1

tropinone

481-37-8

ecgonine

Cr2O3-H2SO4

Cr2O3-H2SO4

532-24-1

tropinone

7664-93-9

sulfuric acid

lead dioxide

lead dioxide

532-24-1

tropinone

Conditions
ConditionsYield
at 60 - 70℃;
50-00-0

formaldehyd

nortropinone

nortropinone

532-24-1

tropinone

Conditions
ConditionsYield
With methanol anschliessenden Hydrieren des Reaktionsgemisches an Raney-Nickel;
potassium permanganate

potassium permanganate

532-24-1

tropinone

Conditions
ConditionsYield
in schwefelsaurer Loesung;
7664-93-9

sulfuric acid

potassium permanganate

potassium permanganate

532-24-1

tropinone

Conditions
ConditionsYield
at 10℃;
potassium ferricyanide

potassium ferricyanide

soda alkaline

soda alkaline

532-24-1

tropinone

tropinone-carboxylic acid-(2)-ethyl ester

tropinone-carboxylic acid-(2)-ethyl ester

532-24-1

tropinone

Conditions
ConditionsYield
With diluted acids
With diluted acids
7647-01-0

hydrogenchloride

1515-26-0, 14587-46-3

tropinone oxime

zinc

zinc

532-24-1

tropinone

532-24-1

tropinone

529-17-9

tropane

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; platinum(IV) oxide under 1.5 Torr; for 35h;100%
With potassium hydroxide; hydrazine In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol for 8h; Wolff-Kischener reduction; Heating;
532-24-1

tropinone

5632-84-8

nortropinone

Conditions
ConditionsYield
Stage #1: tropinone With carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane for 3h; Heating;
Stage #2: In methanol for 5h; Heating;
100%
With DAOP(2+)*2BF4(1-); oxygen In acetonitrile at 20℃; Irradiation;93%
With carbonochloridic acid 1-chloro-ethyl ester In methanol88%
532-24-1

tropinone

1515-26-0, 14587-46-3

tropinone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol for 1h; Reflux;100%
With hydroxylamine hydrochloride; sodium acetate In ethanol Reflux;90%
With pyridine; hydroxylamine hydrochloride In ethanol for 0.833333h; Heating / reflux;66%
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

532-24-1

tropinone

2858-77-7

ethyl (8-methyl-8-azabicyclo<3.2.1>oct-3-ylidene)acetate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h;
Stage #2: tropinone In tetrahydrofuran at 20℃; Further stages.;
99.4%
With potassium hexamethylsilazane In tetrahydrofuran at 20 - 80℃; for 37h; Wadsworth-Emmons reaction;62%
Conditions
ConditionsYield
With C15H18BF3; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 75℃; under 75007.5 Torr; for 24h; Glovebox;96%
With C16H33Cl2CoN5P2; hydrogen; sodium t-butanolate In tert-Amyl alcohol at 20℃; under 15001.5 Torr; for 24h; Autoclave;92%
With 2-methyl-propan-1-ol; sodium In toluene for 24h; Heating;65%
532-24-1

tropinone

541-41-3

chloroformic acid ethyl ester

32499-64-2

N-carbethoxytropinone

Conditions
ConditionsYield
With potassium carbonate In toluene Heating;95%
With potassium carbonate; triethylamine In toluene Heating;95%
With potassium carbonate In toluene Reflux;92%
532-24-1

tropinone

7309-42-4

(+/-)-9-methyl-3,9-diazabicyclo[4.2.1]nonan-4-one

Conditions
ConditionsYield
Stage #1: tropinone With sodium azide; sulfuric acid In chloroform for 2h; Reflux;
Stage #2: With potassium carbonate; potassium hydroxide In chloroform; water
95%
Stage #1: tropinone With sodium azide; sulfuric acid In chloroform for 2h; Reflux;
Stage #2: With potassium carbonate; potassium hydroxide In chloroform; water for 0.166667h;
95%
Stage #1: tropinone With sodium azide; sulfuric acid In chloroform at -5 - 35℃; for 2h; Reflux;
Stage #2: With potassium carbonate; potassium hydroxide In water
95%
532-24-1

tropinone

74-88-4

methyl iodide

6690-08-0

8,8-dimethyl-3-oxo-8-azonia-bicyclo[3.2.1]octane iodide

Conditions
ConditionsYield
In acetone at 20℃; for 1h;92%
at 20℃; for 1h;92%
In ethanol for 2h;91%
872-85-5

pyridine-4-carbaldehyde

532-24-1

tropinone

1251531-74-4

(2E,4E)-8-methyl-2,4-bis((pyridin-4-yl)methylene)-8-aza-bicyclo[3.2.1]octan-3-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃; for 18h;92%
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

532-24-1

tropinone

893429-75-9, 893429-77-1, 183810-37-9

8-Methyl-3-trifluoromethanesulfonyl-oxy-8-azabicyclo[3.2.1]oct-2-ene

Conditions
ConditionsYield
Stage #1: tropinone With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 3h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; Further stages.;
90%
Stage #1: tropinone With potassium hexamethylsilazane In tetrahydrofuran at -78℃;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃;
75%
532-24-1

tropinone

75-07-0

acetaldehyde

(1RS,2SR,1'SR,5SR)-2-(1'-hydroxyethyl)-tropinone

Conditions
ConditionsYield
Stage #1: tropinone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: acetaldehyde In tetrahydrofuran; hexane at -78℃; for 0.666667h; Aldol condensation;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane diastereoselective reaction;
87%
532-24-1

tropinone

162269-90-1

3-bromo-4-(methoxymethoxy)benzaldehyde

C26H27Br2NO5

Conditions
ConditionsYield
With barium dihydroxide In methanol at 20℃; for 2h;86.3%
375-72-4

Nonafluorobutanesulfonyl fluoride

532-24-1

tropinone

rac-8-methyl-8-azabicyclo[3.2.1]oct-2-en-3-yl nonaflate

Conditions
ConditionsYield
Stage #1: tropinone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -50℃; for 0.5h;
Stage #2: Nonafluorobutanesulfonyl fluoride In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Further stages.;
86%
375-72-4

Nonafluorobutanesulfonyl fluoride

532-24-1

tropinone

8-methyl-8-azabicyclo[3.2.1]oct-2-en-3-yl nonaflate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃;86%
concentrated NH4 OH

concentrated NH4 OH

18282-59-2

4-bromo-1,2-dichlorobenzene

532-24-1

tropinone

189746-59-6

3-(3,4-dichloro-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; diethyl ether; water86%
106-37-6

1.4-dibromobenzene

532-24-1

tropinone

3-(4-bromophenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene; tropinone With n-butyllithium In tetrahydrofuran at -75 - -70℃; for 0.5h; Inert atmosphere;
Stage #2: tropinone In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere;
85.2%
532-24-1

tropinone

100-46-9

benzylamine

101353-61-1

3-endo-benzylamino-8-methyl-8-azabicyclo[3.2.1]octane

Conditions
ConditionsYield
With sodium tetrahydroborate; 2-Ethylhexanoic acid In dichloromethane Ambient temperature;85%
With ethanol; platinum at 50℃; Hydrogenation;
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane for 18h; Ambient temperature;
With ethanol; platinum at 50℃; Hydrogenation;
532-24-1

tropinone

135-97-7

pseudotropine

Conditions
ConditionsYield
With lithium borohydride In tetrahydrofuran a) -78 deg C, 6 h, b) RT, overnight;85%
With 2-methyl-propan-1-ol; sodium; toluene
With lithium borohydride In tetrahydrofuran at -78℃;
532-24-1

tropinone

71-43-2

benzene

67171-13-5

3,3-diphenyl-N-methyl-8-azabicyclo[3.2.1]octane

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 20℃; for 3h; Substitution;85%
532-24-1

tropinone

104-88-1

4-chlorobenzaldehyde

1121978-98-0

2,4-bis(4-chlorobenzylidene)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; Inert atmosphere;85%
532-24-1

tropinone

128833-03-4

P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester

1177559-70-4

3-[(3-bromophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octane

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 5h;85%
500-22-1

3-pyridinecarboxaldehyde

532-24-1

tropinone

1251531-75-5

(2E,4E)-8-methyl-2,4-bis((pyridin-3-yl)methylene)-8-aza-bicyclo[3.2.1]octan-3-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃; for 18h;85%
3132-99-8

m-bromobenzoic aldehyde

532-24-1

tropinone

C22H19Br2NO

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling with ice;84%
532-24-1

tropinone

3-endo-amino-8-methyl-8-azabicyclo[3.2.1.]octane bis-hydrochloride

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃;83%
948-65-2

2-phenyl-indole

532-24-1

tropinone

3-(8-methyl-8-aza-bicyclo[3.2.1]oct-2-en-3-yl)-2-phenyl-1H-indole

Conditions
ConditionsYield
With phosphoric acid; acetic acid at 100℃;82%
532-24-1

tropinone

123-11-5

4-methoxy-benzaldehyde

379669-36-0

(2E,4E)-2,4-bis(4-methoxy-benzylidene)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; Inert atmosphere;82%
With sodium hydroxide In ethanol at 20℃; for 0.5h;32%
532-24-1

tropinone

100-52-7

benzaldehyde

C22H21NO

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling with ice;82%
7677-24-9

trimethylsilyl cyanide

532-24-1

tropinone

131444-44-5

(3-Oxo-8-aza-bicyclo[3.2.1]oct-8-yl)-acetonitrile

Conditions
ConditionsYield
With oxygen; N,N'-dimethyl-2,7-diazapyrene bis(tetrafluoroborate) In acetonitrile at 20℃; for 4h; Irradiation; various other tertiary amines, other times;81%
With oxygen; N,N'-dimethyl-2,7-diazapyrene bis(tetrafluoroborate) In acetonitrile at 20℃; for 4h; Irradiation;81%

diacetyl-2-(4-N-allyl-3-thiosemicarbazonato)-3-(4-N-amino-3-thiosemicarbazonato)zinc(II)

532-24-1

tropinone

diacetyl-2-(4-N-allyl-3-thiosemicarbazonato)-3-(4-N-tropimine-3-thiosemicarbazonato)zinc(II)

Conditions
ConditionsYield
In methanol 3-tropinone added to soln. of Zn complex in MeOH under stirring, mixt. heated at reflux for 12-16 h under N2, mixt. allowed to cool slowly to room temp.; ppt. filtered off, washed with cold MeOH and Et2O, dried under vac. at 80°C; elem. anal.;81%
2537-48-6

diethyl 1-cyanomethylphosphonate

532-24-1

tropinone

91817-61-7

2-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetonitrile

Conditions
ConditionsYield
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.25h; Inert atmosphere;
Stage #2: tropinone In tetrahydrofuran; mineral oil at 60℃; for 2h; Inert atmosphere;
80.7%
With sodium hydride In tetrahydrofuran at 25℃; for 2h;

Tropinone Safety Profile

Safety Information of Tropinone (CAS NO.532-24-1):
Hazard Codes:C ,Xi 
Risk Statements:34-22-36/37/38
34:Causes burns
22:Harmful if swallowed 
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:23-24/25-36/37/39-26-22
23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
24/25:Avoid contact with skin and eyes
36/37/39:Wear suitable protective clothing, gloves and eye/face protection   
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
22:Do not breathe dust    
RIDADR:1544
WGK Germany:3
HazardClass:6.1
PackingGroup:III
HS Code:29399990

Tropinone Specification

 The Tropinone, with the CAS registry number 532-24-1,is also known as 3-Tropanone; 8-Methyl-8-azabicyclo[3.2.1]octan-3-one. It belongs to the product categories of Miscellaneous Biochemicals;chiral;Fused Ring Systems. This chemical's molecular formula is C8H13NO and molecular weight is 139.20. What's more,Its systematic name is Tropinone.It is a white to light yellow crystal powde. And it is used as a intermediate to product Atropine sulfate.

Physical properties about Tropinone are:
(1)ACD/LogP:  0.522; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  -2.41; (4)ACD/LogD (pH 7.4):  -1.01; (5)ACD/BCF (pH 5.5):  1.00; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  1.00; (8)ACD/KOC (pH 7.4):  1.36; (9)#H bond acceptors:  2; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  0; (12)Index of Refraction:  1.505; (13)Molar Refractivity:  38.739 cm3; (14)Molar Volume:  130.503 cm3; (15)Surface Tension:  35.5950012207031 dyne/cm; (16)Density:  1.067 g/cm3; (17)Flash Point:  90 °C; (18)Enthalpy of Vaporization:  45.347 kJ/mol; (19)Boiling Point:  217.101 °C at 760 mmHg; (20)Vapour Pressure:  0.135000005364418 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C1CC2N(C)C(C1)CC2;
(2)Std. InChI:InChI=1S/C8H13NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-7H,2-5H2,1H3;
(3)Std. InChIKey:QQXLDOJGLXJCSE-UHFFFAOYSA-N.

Safety Information of Tropinone:
The Tropinone is Harmful if swallowed and Irritating to eyes, respiratory system and skin. And it causes burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .When you use it ,wear suitable protective clothing, gloves and eye/face protection.And do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .Avoid contact with skin and eyes.

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