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744956

Sigma-Aldrich

2-(Tosyloxy)cycloheptanone

≥98% (HPLC)

Synonym(s):

α-Tosyloxycycloheptanone, 2-Hydroxycycloheptanone p-toluenesulfonate, 2-{[(4-Methylphenyl)sulfonyl]oxy}cycloheptanone, Toluene-4-sulfonic acid 2-oxocycloheptyl ester

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About This Item

Empirical Formula (Hill Notation):
C14H18O4S
CAS Number:
146040-84-8
Molecular Weight:
282.36
Beilstein:
5820980
UNSPSC Code:
12352108
PubChem Substance ID:
329765718

Quality Level

100

Assay

≥98% (HPLC)

form

solid

reaction suitability

reaction type: C-C Bond Formation

SMILES string

O=C1CCCCCC1OS(=O)(C2=CC=C(C)C=C2)=O

InChI

1S/C14H18O4S/c1-11-7-9-12(10-8-11)19(16,17)18-14-6-4-2-3-5-13(14)15/h7-10,14H,2-6H2,1H3

InChI key

WVZOAZUIYHADSM-UHFFFAOYSA-N

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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m-Iodosylbenzoic Acid: Recyclable Hypervalent Iodine Reagent for ?-Tosyloxylation and ?-Mesyloxylation of Ketones
Yusubov, M.S., et al.
Synthetic Communications, 39, 3772-3784 (2009)
Reaction of [hydroxy(tosyloxy)iodo]benzene and [hydroxy(mesyloxy)iodo]benzene with trimethylsilyl enol ethers. A new general method for .alpha.-sulfonyloxylation of carbonyl compounds.
Moriarty, R. M., et al.
The Journal of Organic Chemistry, 54, 1101-1104 (1989)
One-step .alpha.-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene
Koser, G.F., et al.
The Journal of Organic Chemistry, 47, 2487-2489 (1982)
Scott T Handy et al.
The Journal of organic chemistry, 70(7), 2874-2877 (2005-03-25)
[structure: see text] We report a homogeneous supported version of Koser's salt based on a room-temperature ionic liquid (RTIL) support. By altering the nature of the RTIL, a material was developed that was stable, recyclable, and readily separable from the
Makoto Ueno et al.
The Journal of organic chemistry, 68(16), 6424-6426 (2003-08-05)
alpha-Tosyloxyketones and alpha-tosyloxyaldehydes were directly prepared from alcohols by treatment with iodosylbenzene and p-toluenesulfonic acid monohydrate in good yields. This method can be used for the direct preparation of thiazoles, imidazoles, and imidazo[1,2-a]pyridines from alcohols in good to moderate yields

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