Thallium(III) nitrate
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| Names | |
|---|---|
| IUPAC name
thallium(III) trinitrate
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| Other names
thallic nitrate
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.033.918 |
PubChem CID
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| UNII | |
| UN number | 2727 |
CompTox Dashboard (EPA)
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| Properties | |
| Tl(NO3)3 | |
| Molar mass | 390.398 g/mol |
| Appearance | colorless solid |
| Density | 3.36 g/cm3 |
| Melting point | 103 °C (217 °F; 376 K) |
| Boiling point | decomposes |
| reacts | |
| Structure | |
| hexagonal | |
| R3 | |
a = 11.821 Å, c = 10.889 Å
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Lattice volume (V)
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1313.7 Å3 |
| Hazards | |
| GHS labelling: | |
  
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| Danger | |
| NFPA 704 (fire diamond) | |
| NIOSH (US health exposure limits): | |
IDLH (Immediate danger)
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15 mg/m3 |
| Safety data sheet (SDS) | Fisher Scientific |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thallium(III) nitrate, also known as thallic nitrate, is a thallium compound with chemical formula Tl(NO3)3.[1] Normally found as the trihydrate, it is a colorless and highly toxic salt which hydrolyses in water to thallium(III) oxide.[2] It is a strong oxidizing agent useful in organic synthesis.
Prepration
[edit]The trihydrate is prepared by dissolving thallium(III) oxide in concentrated nitric acid at 80 °C, followed by cooling of the resulting solution:[3]
- Tl2O3 + 6 HNO3 → 2 Tl(NO3)3 + 3 H2O
Structure
[edit]Thallium(III) nitrate trihydrate, Tl(NO3)3·3H2O, crystallizes in the hexagonal crystal system and consists of a nine-coordinate thallium center with three bidentate nitrate ligands and three monodentate water ligands.[4]
Organic synthesis
[edit]Despite its toxicity, thallium(III) nitrate is sometimes used in the laboratory, such as in the oxidation of methoxyl phenols to quinone acetals:[5]
Another use of thallium(III) nitrate is the oxidization of alkenes to acetals, cyclic alkenes to ring contracted aldehydes, and terminal alkynes to carboxylic acids. Ketones are also oxidized to carboxylic acids or esters in the presence of methanol. Illustrated below is an example of alkene oxidation to an acetal:[5][6]
References
[edit]- ^ "Material Safety Data Sheet". Thermo Fisher Scientific.
- ^ Norman Binsted; Andrew L Hector; William Levason (2000). "Synthesis and properties of thallium(III) periodate". Inorganica Chimica Acta. 298 (1): 116–119. doi:10.1016/S0020-1693(99)00427-2.
- ^ Alexander McKillop; John D. Hunt; Edward C. Taylor; Frank Kienzle (1970). "Thallium in organic synthesis. XX. Oxidative rearrangement of olefins with thallium(III) nitrate: A simple one-step synthesis of aldehydes and ketones". Tetrahedron Letters. 11 (60): 5275–5280. doi:10.1016/S0040-4039(00)99993-3.
- ^ R. Faggiani; I. D. Brown (1978). "Thallium(III) trinitrate trihydrate". Acta Crystallographica B. 34 (5): 1675–1676. doi:10.1107/S0567740878006305.
- ^ a b Sibi, Mukund P.; Silva, Luiz F.; Carneiro, Vânia M. T. (2008-09-15). John Wiley & Sons, Ltd (ed.). Thallium(III) Nitrate Trihydrate. Chichester, UK: John Wiley & Sons, Ltd. doi:10.1002/047084289x.rt085.pub2. ISBN 978-0-471-93623-7.
- ^ Hyo Jin Gim; Hua Li; So Ra Jung; Yong Joo Park; Jae-Ha Ryu; Kyu Hyuck Chung; Raok Jeon (2014). "Design and synthesis of azaisoflavone analogs as phytoestrogen mimetics". European Journal of Medicinal Chemistry. 85: 107–118. doi:10.1016/j.ejmech.2014.07.030.
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