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| CAS No.: | 1669-98-3 |
|---|---|
| Name: | ETHYLMETHYLSULPHOXIDE |
| Molecular Structure: | |
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| Formula: | C3H8 O S |
| Molecular Weight: | 92.1619 |
| Synonyms: | Sulfoxide,ethyl methyl (6CI,7CI,8CI); (?à)-Ethyl methyl sulfoxide; Ethyl methyl sulfoxide; Methyl ethyl sulfoxide |
| Density: | 1.052g/cm3 |
| Boiling Point: | 198.2°Cat760mmHg |
| Flash Point: | 73.7°C |
| PSA: | 36.28000 |
| LogP: | 1.25050 |

| Conditions | Yield |
|---|---|
| With dihydrogen peroxide In neat (no solvent) at 20℃; for 1h; chemoselective reaction; | 97% |
| With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.383333h; chemoselective reaction; | 92% |
| With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.416667h; Green chemistry; chemoselective reaction; | 91% |

methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane

A

Ethyl methyl sulfoxide

B

(2-methylsulfanylvinyl)benzene

| Conditions | Yield |
|---|---|
| With ethylmagnesium chloride In tetrahydrofuran for 1h; Ambient temperature; | A n/a B 82% |

(E)-1-(p-chlorophenyl)-2-(methylsulfinyl)-2-(methylthio)ethene

A

Ethyl methyl sulfoxide

B

1-chloro-4-(2-methylsulfanylvinyl)benzene

| Conditions | Yield |
|---|---|
| With ethylmagnesium chloride In tetrahydrofuran for 1h; Ambient temperature; | A 37% B 79% |

| Conditions | Yield |
|---|---|
| With C30H24N2O7W; dihydrogen peroxide In dichloromethane; water for 1h; Reflux; | A 30% B 70% |
| With dihydrogen peroxide; [MoO(O2)2(C9H6ON)][PPh4] In dichloromethane at 40℃; for 1h; Product distribution; Further Variations:; Catalysts; Reagents; | A 50 % Chromat. B 48 % Chromat. |
| With tert.-butylhydroperoxide; aluminum tri-tert-butoxide In benzene | A n/a B 20 % Chromat. |

A

Ethyl methyl sulfoxide

B

1-Methyl-4-((Z)-2-methylsulfanyl-vinyl)-benzene

| Conditions | Yield |
|---|---|
| With ethylmagnesium chloride In tetrahydrofuran for 1h; Ambient temperature; | A n/a B 60% |

A

Ethyl methyl sulfoxide

| Conditions | Yield |
|---|---|
| With ethylmagnesium chloride In tetrahydrofuran for 1h; Ambient temperature; | A n/a B 41% |

furan


1-bromo-2-(methylsulfinyl)benzene


ethylmagnesium bromide

A

1,4-dihydronaphthalene-1,4-epoxide

B

Ethyl methyl sulfoxide

| Conditions | Yield |
|---|---|
| 1.) THF, 60 deg C, 11 h; Yield given. Multistep reaction. Yields of byproduct given; |


acetic anhydride


3-O-(β-D-galactopyranosyl)-D-arabinose


methyl iodide

A

Ethyl methyl sulfoxide

B

1,3,4-tri-O-acetyl-2,5-di-O-methyl-D-arabinitol

C

1,5-di-O-acetyl-2,3,4,6-tetra-O-methyl-D-galactitol

D

1,3,5-tri-O-acetyl-2,4-di-O-methyl-D-arabinitol

E

trimethylsulfoxonium iodide

| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; perchloric acid; trimethylsulfoxonium iodide; trifluoroacetic acid In dimethyl sulfoxide Product distribution; Improved methylation analysis; other saccharides; |


(η5-cyclopentadienyl)Re(NO)(P(C6H5)3)(CF3SO3)


Ethyl methyl sulfoxide


[(η5-C5H5)Re(NO)(PPh3)(S(=O)(Me)Et)]TfO

| Conditions | Yield |
|---|---|
| In chlorobenzene stirred for 5 h at room temp.; ppt. filtered off, washed (PhCl, ether), dried (vac.); obtained as a mixt. of diastereomers; | 93% |

potassium tetrachloroplatinate(II)


Ethyl methyl sulfoxide


K[Pt(ethylmethylsulfoxide)Cl3]

| Conditions | Yield |
|---|---|
| In water byproducts: KCl; aq. soln. of Pt compd. mixed with ligand (1:1), stirred at room temp. for 24 h; filtered, evapd., treated (acetone), filtered, evapd., washed (Et2O), dried (vac.); | 75% |