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641588

Sigma-Aldrich

Dodecyl methyl sulfoxide

98%

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About This Item

Empirical Formula (Hill Notation):
C13H28OS
CAS Number:
Molecular Weight:
232.43
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

solid

mp

59-63 °C (lit.)

functional group

sulfoxide

SMILES string

CCCCCCCCCCCCS(C)=O

InChI

1S/C13H28OS/c1-3-4-5-6-7-8-9-10-11-12-13-15(2)14/h3-13H2,1-2H3

InChI key

CJPDBKNETSCHCH-UHFFFAOYSA-N

General description

Dodecyl methyl sulfoxide can be synthesized via oxidation of dodecyl methyl sulfide with sodium periodate.

Application

Dodecyl methyl sulfoxide can be used as a substitute for dimethyl sulfoxide in Swern oxidation of primary allylic and benzylic alcohols to the corresponding aldehydes and secondary alcohols to the corresponding ketones.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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"New odorless method for the Corey?Kim and Swern oxidations utilizing dodecyl methyl sulfide (Dod-S-Me)"
Ohsugi I-S, et al.
Tetrahedron, 59(42), 8393-8398 (2003)
"New non-volatile and odorless organosulfur compounds anchored on ionic liquids. Recyclable reagents for Swern oxidation"
He X and Chan HT
Tetrahedron, 62(14), 3389-3394 (2006)
"New odourless protocols for efficient Pauson?Khand annulations"
Brown.AJ, et al.
Organic & Biomolecular Chemistry, 3(13), 2396-2398 (2005)

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