[Hydroxy(tosyloxy)iodo]benzene
Synonym(s):HTIB;Koser’s reagent;Phenyliodosyl hydroxide tosylate;Hydroxy(4-methylbenzenesulfonato-O)phenyliodine;Hydroxy(phenyl)iodo tosylate
- CAS NO.：27126-76-7
- Empirical Formula: C13H13IO4S
- Molecular Weight: 392.21
- MDL number: MFCD00011547
- EINECS: 629-501-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-05-14 16:41:43
![[Hydroxy(tosyloxy)iodo]benzene Structural](https://img.chemicalbook.in/CAS/GIF/27126-76-7.gif)
What is [Hydroxy(tosyloxy)iodo]benzene?
Chemical properties
Pale yellow crystalline powder
The Uses of [Hydroxy(tosyloxy)iodo]benzene
Versatile synthetic reagent in phenyliodination and/or tosylation of a range of organic substrates; in oxidative transformations including oxidative rearrangements.
The Uses of [Hydroxy(tosyloxy)iodo]benzene
Reactant for:
- Ligand-free palladium-catalyzed Heck-type coupling reactions
- Preparation of carbodiimides via dehydrosulfurization of thioureas
- Preparation of nitriles by oxidative conversion of alcohols, aldehydes, and amines
- Preparation of substituted anilines via aromatic aldoxime reaction
- Preparation of tetrahydrofurans by oxidative cyclization of homoallylic alcohols
- Preparation of isoxazoline N-Oxides from ?-hydroxyketoximes via oxidative N-O coupling
- Ring expansion in synthesis of aminopeptidase inhibitors
- Oxidation and protonation reactions in acidic conditions
Purification Methods
Possible impurities are tosic acid (removed by washing with Me2CO) and acetic acid (removed by washing with Et2O). It is purified by dissolving in the minimum volume of MeOH, adding Et2O to cloud point and setting aside for the prisms to separate [Koser & Wettach J Org Chem 42 1476 1977, NMR: Koser et al. J Org Chem 41 3609 1976]. It has also been crystallised from CH2Cl2 (needles, m 140-142o) [Neiland & Karele J Org Chem, USSR (Engl Transl) 6 889 1970].
Properties of [Hydroxy(tosyloxy)iodo]benzene
| Melting point: | 131-137 °C (lit.) |
| storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
| solubility | soluble in Methanol |
| form | Crystalline Powder |
| pka | 7.59±0.58(Predicted) |
| color | Pale yellow |
| Sensitive | Light Sensitive |
| Merck | 14,5321 |
| BRN | 2150074 |
| CAS DataBase Reference | 27126-76-7(CAS DataBase Reference) |
Safety information for [Hydroxy(tosyloxy)iodo]benzene
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
| Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for [Hydroxy(tosyloxy)iodo]benzene
| InChIKey | LRIUKPUCKCECPT-UHFFFAOYSA-N |
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