Maximum quantity allowed is 999
CAS RN: 3240-34-4 | Product Number: I0330
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|Purity / Analysis Method||>97.0%(T)|
|Molecular Formula / Molecular Weight||C__1__0H__1__1IO__4 = 322.10|
|Physical State (20 deg.C)||Solid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Moisture Sensitive|
|Reaxys Registry Number||1879369|
|PubChem Substance ID||87571686|
|SDBS (AIST Spectral DB)||12662|
|Appearance||White to Light yellow powder to crystal|
|Purity(Iodometric Titration)||min. 97.0 %|
|Solubility in Methanol||almost transparency|
|Melting Point||158 °C(dec.)|
|Solubility in water||Insoluble|
|Solubility (soluble in)||Methanol|
|Solubility (insoluble in)||Ether|
|Hazard Statements||H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
|Precautionary Statements||P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
To a solution of 1-naphthalenemethanol (306 mg, 2.0 mmol) in dichloromethane (2 mL, 1.0 mol/L) was added TEMPO (31.2 mg, 0.20 mmol), PhI(OAc)2 (709mg, 2.2 mmol) and the mixture was stirred at room temperature for 4 hours. Dichloromethane (12.5 mL), saturated aqueous sodium thiosulfate solution (12.5 mL) was added and the mixture was stirred for 30 minutes. The organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL), brine (10 mL) and the organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 0:100 - 3:97 on silica gel) to give 1-naphthaldehyde as a yellow liquid (291 mg, 93%).
The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:9, Rf = 0.50).
1H NMR (400 MHz, CDCl3); δ 10.41 (s, 1H), 9.26 (d, J = 8.9 Hz, 1H), 8.11 (d, J = 8.4 Hz, 1H), 8.01 (d, J = 6.8 Hz, 1H), 7.93 (d, J = 8.9 Hz, 1H), 7.74-7.57 (m, 3H).
- 2-(Hydroxyimino)aldehydes: Photo- and Physicochemical Properties of a Versatile Functional Group for Monomer Design
To a solution of 2-phenylimidazoline (500 mg, 3.4 mmol), potassium carbonate (520 mg, 3.8 mmol, 1.1 equiv) in DMSO (17 mL) was added iodobenzene diacetate (1.21 g, 3.8 mmol, 1.1 equiv) and stirred at rt for 18 hours. The residue was diluted with ethyl acetate (75 mL) and washed with saturated aqueous sodium bicarbonate solution (50 mL, twice) dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on aminosilica gel, ethyl acetate:hexane = 0:1 - 1:0), giving 2-phenylimidazole as a white solid (340 mg，y. 69%).
The reaction mixture was monitored by NH-TLC (ethyl acetate, Rf = 0.30).
1H NMR (270 MHz, DMSO-d6); δ 12.5 (dr, 1H), 7.95-7.91 (m, 2H), 7.44 (t, 2H, J = 7.3 Hz), 7.33 (t, 1H, J = 7.3 Hz), 7.24 (s, 1H), 7.02 (s, 1H)
- Expanded applicability of iridium(I) NHC/phosphine catalysts in hydrogen isotope exchange processes with pharmaceutically-relevant heterocycles
- G. Piancatelli, F. Leonelli, Org. Synth. 2006, 83, 18.
[TCI Practical Example] TEMPO Oxidation Utilizing Iodobenzene Diacetate as a Reoxidant
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