ChemicalBook > CAS DataBase List > Tropinone

Tropinone

Product Name
Tropinone
CAS No.
532-24-1
Chemical Name
Tropinone
Synonyms
Tropanone;3-Tropinone;8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-ONE;Tropanon;Tropinon;ropinone;TROPINONE;NSC 118012;TROPIONONE;3-TROPANONE
CBNumber
CB2470768
Molecular Formula
C8H13NO
Formula Weight
139.2
MOL File
532-24-1.mol
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Tropinone Property

Melting point:
40-44 °C(lit.)
Boiling point:
113 °C25 mm Hg(lit.)
Density 
1.0268 (rough estimate)
refractive index 
1.4598 (estimate)
Flash point:
194 °F
storage temp. 
Inert atmosphere,2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
8.93±0.20(Predicted)
form 
crystalline
color 
brown
PH
8 (18g/l, H2O, 20℃)
BRN 
2329
InChIKey
QQXLDOJGLXJCSE-KNVOCYPGSA-N
CAS DataBase Reference
532-24-1(CAS DataBase Reference)
NIST Chemistry Reference
8-Azabicyclo[3.2.1]octan-3-one, 8-methyl-(532-24-1)
EPA Substance Registry System
8-Azabicyclo[3.2.1]octan-3-one, 8-methyl- (532-24-1)
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Safety

Hazard Codes 
C,Xi
Risk Statements 
34-22-36/37/38
Safety Statements 
23-24/25-36/37/39-26-22
RIDADR 
1544
WGK Germany 
3
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
29399990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T89605
Product name
Tropinone
Purity
99%
Packaging
5g
Price
$49.3
Updated
2024/03/01
Sigma-Aldrich
Product number
T89605
Product name
Tropinone
Purity
99%
Packaging
10g
Price
$78.9
Updated
2024/03/01
TCI Chemical
Product number
T0626
Product name
Tropinone
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$36
Updated
2024/03/01
TCI Chemical
Product number
T0626
Product name
Tropinone
Purity
>98.0%(GC)(T)
Packaging
25g
Price
$122
Updated
2024/03/01
Alfa Aesar
Product number
L02011
Product name
Tropinone, 99%
Packaging
5g
Price
$39.65
Updated
2024/03/01
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Tropinone Chemical Properties,Usage,Production

Description

Tropinone (8-methyl-8-azabicyclo[3.2.1]octane-3-one)(7) is the simplest plant tropane and is the first intermediate in the biosynthesis of tropane alkaloids.  Studies have called 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoic acid as an intermediate metabolite in tropinone biosynthesis[1]. It is an intermediate of atropine sulfate and is used in the synthesis of atropine. Atropine is an anticholinergic drug. It acts as an M-blocker and is indicated for the relief of visceral colic.

Chemical Properties

Tropinone is a white to light yellow crystal powder, It is an alkaloid and a precursor to a number of additional plant alkaloids. Tropinone is the first intermediate in the biosynthesis of the pharmacologically important tropane alkaloids that possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Chemical synthesis of tropinone was achieved in 1901 but the mechanism of tropinone biosynthesis has remained elusive.

Uses

Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids.

Preparation

The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine.
The 1917 synthesis by Robinson is considered a legend in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methyl amine and acetone dicarboxylic acid (or even acetone). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis. Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%.

References

1. Arthur J. Birch. Investigating a Scientific Legend: The Tropinone Synthesis of Sir Robert Robinson, F.R.S. Notes and Records of the Royal Society of London, 1993, 47, 277-296. DOI:10.1098/rsnr.1993.0034
2. Andrew J. Humphrey and David O'Hagan. Tropane alkaloid biosynthesis. A century old problem unresolved. Natural Products Reports 2001, 18, 494-502. DOI:10.1039/b001713m
3. Tropinone synthesis via an atypical polyketide synthase and P450-mediated cyclization DOI:10.1038/s41467-018-07671-3
4. R. Robinson (1917). "A synthesis of tropinone". Journal of the Chemical Society, Transaction 111: 762 - 768. doi:10.1039/CT9171100762

Tropinone Preparation Products And Raw materials

Raw materials

1,3-Acetonedicarboxylic acid Succinaldehyde 1-amino-2-propanone

Preparation Products

8-Methyl-8-azabicyclo[3.2.1]octan-3-amine dihydrochloride N-Boc-Nortropinone TROPYL A ORMULPHENYLACETATE
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View Lastest Price from Tropinone manufacturers

Dorne Chemical Technology co. LTD
Product
Tropinone 532-24-1
Price
US $10.00/ASSAYS
Min. Order
1ASSAYS
Purity
99%
Supply Ability
100kg
Release date
2024-03-26
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Tropinone 532-24-1
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%min GC
Supply Ability
500KGS
Release date
2021-07-15
Hebei Miaoyin Technology Co.,Ltd
Product
Tropinone 532-24-1
Price
US $30.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
10000
Release date
2023-04-04

532-24-1, TropinoneRelated Search:

Nortropine Bensulfuron methyl Norgestrel Tolperisone hydrochloride Kresoxim-methyl Mesotrione 4-Methyl-2-pentanone Tropicamide N-Methyl-2-pyrrolidone Methyl acrylate Methylparaben Tropine Tropine-3-thiol Tropine-3-thiol hydrochloride Methyl Methyl bromide N-Cbz-Nortropinone N-CARBETHOXY-4-TROPINONE,N-(ETHOXYCARBONYL)TROPINONE,N-(Ethoxycarbonyl)tropinone,99%,n-(carboethoxy)tropinone,N-CARBETHOXY-4-TROPINONE,98%

  • TIMTEC-BB SBB006924
  • 1αH,5αH-Tropan-3-one
  • NSC 118012
  • 1αH,5αH-Tropan-3-one (8CI)
  • Tropanone (6CI)
  • Tropinone (7CI)
  • 8-Methyl-2-({3-oxo-8-azabicyclo[3.2.1]octan-8-yl}Methyl)-8-azabicyclo[3.2.1]octan-3-one
  • 8-Azabicyclo[3.2.1]octan-3-one, 8-methyl-
  • 1-Methyl-2,6-ethanopiperidine-4-one
  • 8-Methyl-3,6-epiminocycloheptane-1-one
  • Tropane-3-one
  • TROPINONE
  • TROPIONONE
  • (1S,5R)-8-METHYL-8-AZA-BICYCLO[3.2.1]OCTAN-3-ONE
  • 8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-ONE
  • 1Ah,5ah-tropan-3-one
  • 1alphaH,5alphaH-Tropan-3-one
  • 3-Tropinone
  • 8-Methyl-8-azabicyclo[3.2.1]-3-octanone
  • N-Methyl-8-azabicyclo[3.2.1]octan-3-one
  • Tropanon
  • Tropanone
  • Tropinon
  • 3-TROPANONE
  • Tropinone,99%
  • Tropinone,98%
  • (1R,5S)-8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-ONE
  • tropan-3-one
  • 8-METHYL-8-AZABICYCLO[3,2,1]OCTANE-3-ONE
  • 8-METHYL-8-AZABICYCLO[3.3.1]OCTAN-3-ONE
  • 8-METHYL-8-AZABICYCLO[3,3,1OCTANE-3-ONE
  • Atropine Impurity 9
  • Manufacturers wholesale top quality CAS:532-24-1 Top quality Tropinone CAS NO.532-24-1
  • Tropinone 99.5%
  • Tropan-3-on
  • Tropinone &gt
  • (1R,5S)-8-methyl-3-oxo-8-azoniabicyclo[3.2.1]octane
  • Tropinone Powder
  • API Tadalafil
  • ropinone
  • 2-Dimethylaminoisopropyl chloride hydrochloride4584-49-0
  • Tropinone cas532-24-1
  • Alpha-tropinone
  • Tropinone (8-methyl-8-Azabicyclo[3.2.1]Octan-3-One)
  • Sulfuric acid iron(2+) salt monohydrate 17375-41-6
  • Atropine Impurity 1 (Tropinone)
  • Tropinone-RM
  • 532-24-1
  • C8H13NO
  • C7 to C8
  • Carbonyl Compounds
  • Building Blocks
  • N-Containing
  • Others
  • Organic Building Blocks
  • Ketones
  • Heterocyclic Building Blocks
  • Miscellaneous Biochemicals