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Published TCIMAIL newest issue No.201
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CAS RN: 27126-76-7 | Product Number: P1015
[Hydroxy(tosyloxy)iodo]benzene
![Thumbnail of [Hydroxy(tosyloxy)iodo]benzene](/medias/P1015.jpg?context=bWFzdGVyfHJvb3R8MTQxNzN8aW1hZ2UvanBlZ3xhRGcwTDJoaFlpODRPVE0yTXpZNU5ESXlNelkyTDFBeE1ERTFMbXB3Wnd8MTNmYjdhMDg3OTJjYWFhNjg1OTY4NWZkMDJkYTI4MzkyMDRkNzZiNDgzZmViMDg3NTI0M2E3OWI2YTlmMTczMw "[Hydroxy(tosyloxy)iodo]benzene")
![Chemical Structure of [Hydroxy(tosyloxy)iodo]benzene](/medias/P1015.jpg?context=bWFzdGVyfHJvb3R8NDM5MTl8aW1hZ2UvanBlZ3xhREUzTDJneFl5ODRPVEl5T1RBek1qZ3hOamswTDFBeE1ERTFMbXB3Wnd8YTU3MWIwOTdmMTA4NDEwNDgwZmYxMThkYTI5YTA4YzVhNWYwOGY3MGIxMDdhNGE5MTgxMDJlOWQyYWIyYThhMg "[Hydroxy(tosyloxy)iodo]benzene")
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![[Hydroxy(tosyloxy)iodo]benzene](/_ui/responsive/theme-tci/images/missing_product_zoom.webp "[Hydroxy(tosyloxy)iodo]benzene")
Purity: >97.0%(T)
Synonyms:
- Phenyliodosohydroxy Tosylate
- Koser Reagent
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
Shipping Information
|
|---|---|---|---|---|---|
| 5G |
€ 76,00
|
1 | 35 |
|
|
| 25G |
€ 301,00
|
1 | 28 |
|
* Stock available in Belgium: Shipment on the same day
* Stock available in Japan: Please check the Shipping Simulation for estimated shipments. (excludes regulated items and dry ice shipments)
| Product Number | P1015 |
Purity / Analysis Method 
|
>97.0%(T) |
| Molecular Formula / Molecular Weight | C__1__3H__1__3IO__4S = 392.21 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Room Temperature (Recommended in a cool and dark place, <15°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Light Sensitive,Moisture Sensitive |
| CAS RN | 27126-76-7 |
| Reaxys Registry Number | 2150074 |
| PubChem Substance ID | 87575127 |
| SDBS (AIST Spectral DB) | 18485 |
| Merck Index (14) | 5321 |
| MDL Number | MFCD00011547 |
Specifications
| Appearance | White to Light yellow powder to crystal |
| Purity(Neutralization titration) | min. 97.0 % |
| Purity(Iodometric Titration) | min. 97.0 % |
| Solubility in Methanol | very faint turbidity |
Properties (reference)
| Melting Point | 138 °C |
| Solubility (soluble in) | Methanol |
GHS
| Pictogram |
|
| Signal Word | Warning |
| 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. |
Related Laws:
Transport Information:
| HS Number | 2931900090 |
Application
Deprotection of Bn Groups using Koser Reagent
Reference
- Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
- P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.
Application
Oxidative Umpolung α‑Alkylation of Ketones
Typical Procedure: (R1 = Ph, R2 = CO2Et, R3 = CH3): Ethyl 3-oxo-3-phenylpropanoate (0.58 mmol, 110 mg, 1 eq.) is dissolved in anhydrous toluene (1.45 mL) under an argon atmosphere. After cooling to -78 °C, [hydroxy(tosyloxy)iodo]benzene (1.16 mmol, 0.45 g, 2 eq.) and dried MgSO4 (2.9 mmol, 0.35 g, 5 eq.) are added in the dark. Then a solution of dimethylzinc in toluene (1.2 M, 1.16 mmol, 0.97 mL, 2 eq.) is added at once. The mixture is allowed to stir at -78 °C for 18 h, in the dark. The reaction is quenched by addition of water, followed by filtration of the slurry through a Celite frit and rinsed with CH2Cl2. The product is purified by a column chromatography (eluent: 5-15% of EtOAc/hexane) to give ethyl 2-methyl-3-oxo-3-phenylpropanoate as an oil (110 mg, 92% yield).
References
More information on umpolung is available on our website
TCI Mail No.157
TCI Mail No.157
Application
Oxidative Umpolung alkylation of Evans’ β-ketoimides
Szpilman et al. have reported [hydroxy(tosyloxy)iodo]benzene mediated the alkylative umpolung reaction of Evans’ β-ketoimides with dialkylzinc reagents.
References
Application
Tosyloxylation
References
- G. F. Koser, R. H. Wettach, C. S. Smith, J. Org. Chem. 1980, 45, 1543.
- G. F. Koser, A. G. Relenyi, A. N. Kalos, L. Rebrovic, R. H. Wettach, ibid. 1982, 47, 2487.
- G. F. Koser, L. Rebrovic, R. H. Wettach, ibid. 1981, 46, 4324.
PubMed Literature
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