[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

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.