(2-Ethoxy-2-oxoethyl)dimethylsulfonium bromide

Name: (2-Ethoxy-2-oxoethyl)dimethylsulfonium bromide
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CAS No. 5187-82-6
Cat. No. CS-0167158
Purity≥95%
MDL No.MFCD00830557

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(2-Ethoxy-2-oxoethyl)dimethylsulfonium bromide|CS-0167158

Structure of 5187-82-6

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General Information

CAS No. 5187-82-6
Cat. No. CS-0167158
Purity ≥95%
MDL No. MFCD00830557
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₁₃BrO₂S
Molecular Weight 229.14
Synonym(s) (Ethoxycarbonylmethyl)dimethylsulfonium bromide
SMILES C[S+](CC(OCC)=O)C.[Br-]

Description

(Ethoxycarbonylmethyl)dimethylsulfonium bromide was used in synthesis of -sulfanyl--amino acid derivatives by using nanocrystalline magnesium oxide. It was used during cyclopropanation of (-)-(S)-2-(p-tolylsulfinyl)cyclopent-2-enone.

Application

(2-Ethoxy-2-oxoethyl)dimethylsulfonium bromide serves as a reliable reagent for the synthesis of α-alkylated carbonyl compounds via sulfonium-mediated enolate formation. Its bench-stable nature and compatibility with diverse functional groups enable efficient C–C bond formation under mild conditions. The reagent facilitates regioselective alkylation of ketones and esters, offering straightforward purification and high reproducibility in standard organic synthesis workflows.

Synthesis

Route1
- 75-18-3
- 105-36-2
- ~85%
- In-stock
  
  5187-82-6
References
- SLIL Biomedical Corporation Patent: US2003/195377 A1, 2003 ; Location in patent: Page/Page column 9-10 ;
Route2
- 105-36-2
- ~%
- In-stock
  
  5187-82-6
References
- Eli Lilly and Company Patent: US5661184 A1, 1997 ; US 5661184 A

Safety Information

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Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 26.3
LogP -2.5686
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Thioether

Building Blocks Functional Group Ester

Key Words

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(2-Ethoxy-2-oxoethyl)dimethylsulfonium bromide

CAS No. 5187-82-6

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