2-(phenylsulfanyl)ethan-1-ol

• ChemBase ID: 8013
• Molecular Formular: C8H10OS
• Molecular Mass: 154.2294
• Monoisotopic Mass: 154.04523594
• SMILES: c1cccc(c1)SCCO
• Canonical SMILES: OCCSc1ccccc1
• InChI: InChI=1S/C8H10OS/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2
• InChIKey: KWWZHCSQVRVQGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(phenylsulfanyl)ethan-1-ol
• IUPAC Traditional name: 2-(phenylsulfanyl)ethanol
• Synonyms: 2-Hydroxyethyl phenyl sulfide; 2-(Phenylthio)ethanol; 2-Hydroxyethyl phenyl sulfide; 2-Hydroxyethyl phenyl sulphide; 2-(Phenylthio)ethanol 98%; 2-(苯硫基)乙醇; 2-羟乙基苯硫醚; 2-苯硫基乙醇

Database IDs

• CAS Number: 699-12-7
• EC Number: 211-828-9
• MDL Number: MFCD00002905
• Beilstein Number: 1860057
• PubChem SID: 160971320; 24853928
• PubChem CID: 69685

CALCULATED PROPERTIES

• Acid pKa: 15.486968
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.6516755
• LogD (pH = 7.4): 1.6516755
• Log P: 1.6516755
• Molar Refractivity: 45.3124 cm^3
• Polarizability: 17.679407 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 115-116 °C/2 mmHg(lit.); 115-116°C; 115-116°C/2mm; 115-116°C/2mm
• Flash Point: >110°C; >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.143; 1.143 g/mL at 25 °C(lit.); 1.147
• Refractive Index: 1.5899; 1.5905; n20/D 1.592; n20/D 1.592(lit.)

Safety Information

• Storage Warning: STENCH
• German water hazard class: 3
• Safety Statements: 24/25
• TSCA Listed: true; 是
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥98.0% (GC); 99%
• Grade: purum
• Linear Formula: C6H5SCH2CH2OH

DETAILS

Sigma Aldrich - 232777

Packaging
50 g in glass bottle

REFERENCES

• Reagent for phosphate protection in oligonucleotide synthesis. The resulting esters are stable to base, sulfonylation, and to mild acid, but can be deprotected by periodate oxidation to the sulfoxide: Can. J. Chem., 50, 456, 769 (1972), or NCS oxidation to the sulfone: J. Am. Chem. Soc., 95, 2020 (1973), either of which can then be cleaved by base-induced elimination. For use in pyrimidine protection of thymidine analogs, via Mitsunobu N-alkylation, m-CPBA oxidation to the sulfone and cleavage with dilute NaOH, see: Synlett, 845 (2006).