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Tropinone

CAS No.532-24-1
Chemical Name:Tropinone
CBNumber:CB2470768
Molecular Formula:C8H13NO
Formula Weight:139.2
MOL File:532-24-1.mol

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)
form crystalline
pka 8.93±0.20(Predicted)
color brown
PH 8 (18g/l, H2O, 20℃)
BRN 2329
InChIKey QQXLDOJGLXJCSE-KNVOCYPGSA-N
CAS DataBase Reference 532-24-1(CAS DataBase Reference)
FDA UNII 2A8CC8KA5F
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)
UNSPSC Code 12352100
NACRES NA.22

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

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302+H332
Precautionary statements P261-P264-P270-P271-P301+P312-P304+P340+P312

Tropinone Price More Price(10)

Brand: Sigma-Aldrich(India)
Product number: T89605
Product name : Tropinone
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Brand: Sigma-Aldrich(India)
Product number: T89605
Product name : Tropinone
Purity: 99%
Packaging: 10G
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Brand: Sigma-Aldrich(India)
Product number: T89605
Product name : Tropinone
Purity: 99%
Packaging: 50G
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Brand: ALFA India
Product number: ALF-L02011-22
Product name : Tropinone, 99%
Purity:
Packaging: 100g
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Brand: ALFA India
Product number: ALF-L02011-14
Product name : Tropinone, 99%
Purity:
Packaging: 25g
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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