(2-ethoxy-2-oxoethyl)dimethylsulfanium bromide

• ChemBase ID: 89878
• Molecular Formular: C6H13BrO2S
• Molecular Mass: 229.13522
• Monoisotopic Mass: 227.98196266
• SMILES: O(CC)C(=O)C[S+](C)C.[Br-]
• Canonical SMILES: CCOC(=O)C[S+](C)C.[Br-]
• InChI: InChI=1S/C6H13O2S.BrH/c1-4-8-6(7)5-9(2)3;/h4-5H2,1-3H3;1H/q+1;/p-1
• InChIKey: JXFPTJYKYKVENJ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-ethoxy-2-oxoethyl)dimethylsulfanium bromide
• IUPAC Traditional name: (2-ethoxy-2-oxoethyl)dimethylsulfanium bromide
• Synonyms: (Ethoxycarbonylmethyl)dimethylsulfonium bromide; (Carboethoxymethyl)dimethylsulfonium bromide; (Ethoxycarbonylmethyl)dimethylsulphonium bromide; (乙氧基羰基甲基)二甲基溴化硫鎓

Database IDs

• CAS Number: 5187-82-6
• EC Number: 225-968-3
• MDL Number: MFCD00830557; MFCD00031604
• Beilstein Number: 4161472
• PubChem SID: 162076733; 24848710
• PubChem CID: 78861

CALCULATED PROPERTIES

• Acid pKa: 18.935966
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.4078793
• LogD (pH = 7.4): -0.4078793
• Log P: -0.4078793
• Molar Refractivity: 38.153 cm^3
• Polarizability: 15.975121 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 80(dec.)°C; 90-94 °C(lit.); ca 80°C dec.

Safety Information

• Storage Warning: Irritant/Light Sensitive/Hygroscopic/Store under Argon/Keep Cold
• RTECS: WR7600000
• European Hazard Symbols: Irritant (Xi)
• UN Number: 3448
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3448 6.1/PG 2

Product Information

• Purity: 97%; 98%
• Linear Formula: C2H5O2CCH2S(CH3)2Br

DETAILS

Sigma Aldrich - 145262

Packaging
25 g in glass bottle

REFERENCES

• The derived ylide does not add to carbonyl compounds, although it does undergo 1,4-addition to enones, with formation of cyclopropanecarboxylic esters: Tetrahedron, 23, 545, (1967); J. Org. Chem., 34, 1240 (1969).
• Review of the chemistry of sulfonium ylides: Russ. Chem. Rev., 50, 481 (1981).