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CAS RN: 27126-76-7 | Product Number: P1015

[Hydroxy(tosyloxy)iodo]benzene


Purity: >97.0%(T)
Synonyms:
  • Phenyliodosohydroxy Tosylate
  • Koser Reagent
Documents:
5G
€29.00
1   ≥20 
25G
€93.00
1   17  

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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
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 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

P1015

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


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


PubMed Literature


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