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Sigma-Aldrich

2-(Methylthio)cyclohexanone

98%

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About This Item

Linear Formula:
CH3SC6H9(=O)
CAS Number:
52190-35-9
Molecular Weight:
144.23
MDL number:
MFCD00209603
UNSPSC Code:
12352100
PubChem Substance ID:
24866619

assay

98%

form

liquid

refractive index

n20/D 1.508 (lit.)

bp

45 °C/10.1 mmHg (lit.)

density

1.069 g/mL at 25 °C (lit.)

SMILES string

CSC1CCCCC1=O

InChI

1S/C7H12OS/c1-9-7-5-3-2-4-6(7)8/h7H,2-5H2,1H3

InChI key

QFABNUVNDKOIEH-UHFFFAOYSA-N

General description

2-(Methylthio)cyclohexanone is a 2-substituted cyclohexanone. The proportion of axial and equatorial conformation has been measured in chloroform by the Eliel method. It suggests that the in chloroform steric effect dominates over polar effect in contributing to the conformational preference. The stereoselectivity of the reduction of 2-(methylthio)cyclohexanone using different hydrides has been studied.

Application

2-(Methylthio)cyclohexanone may be used as a ketone substrate for the synthesis of cyclic nitrones, by reacting with aspergillusol A.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

192.2 °F - closed cup

flash_point_c

89 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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Axial/equatorial proportions for 2-substituted cyclohexanones.
Basso EA, et al.
The Journal of Organic Chemistry, 58(27), 7865-7869 (1993)
Studies on the stereoselectivity of hydride reductions on 2-(methylthio)-and 2-(methylsulfonyl) cyclohexanones.
Carmen CM, et al.
The Journal of Organic Chemistry, 52(16), 3619-3625 (1987)
Nitrone formation in phosphate buffer and aqueous solutions: novel chemistry inspired by a natural product.
Pansanit A, et al.
Tetrahedron Letters, 53(16), 2129-2131 (2012)

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