(prop-2-en-1-ylsulfanyl)benzene

• ChemBase ID: 158182
• Molecular Formular: C9H10S
• Molecular Mass: 150.2407
• Monoisotopic Mass: 150.05032132
• SMILES: C=CCSc1ccccc1
• Canonical SMILES: C=CCSc1ccccc1
• InChI: InChI=1S/C9H10S/c1-2-8-10-9-6-4-3-5-7-9/h2-7H,1,8H2
• InChIKey: QGNRLAFFKKBSIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (prop-2-en-1-ylsulfanyl)benzene
• IUPAC Traditional name: allyl phenyl sulfide
• Synonyms: Allyl phenyl sulfide; 烯丙基苯基硫醚; 烯丙氧基苯硫酚

Database IDs

• CAS Number: 5296-64-0
• EC Number: 226-142-5
• MDL Number: MFCD00014957
• Beilstein Number: 1856940
• PubChem SID: 162252318; 24845908
• PubChem CID: 79180

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.2289348
• LogD (pH = 7.4): 3.2289348
• Log P: 3.2289348
• Molar Refractivity: 48.0288 cm^3
• Polarizability: 18.720472 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 223-225 °C(lit.); 223-225°C
• Flash Point: >98°C(208°F); 208.4 °F; 98 °C
• Density: 1.024; 1.024 g/mL at 20 °C(lit.)
• Refractive Index: 1.5740; n20/D 1.572

Safety Information

• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 20/21; 20/21/22
• Safety Statements: 23-36/37; 23-36/37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332; H312-H332
• GHS Precautionary statements: P261-P280H; P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 2

Product Information

• Purity: ≥96.5% (GC); 97%
• Linear Formula: CH2=CHCH2SC6H5

REFERENCES

• Grignard reagents can be allylated with allylic sulfides in the presence of a Ni or Pd catalyst: Tetrahedron Lett., 3425 (1979).
• The lithiated derivative can react with electrophiles at either the ɑ- or - postion. It was found that conversion of the organolithium to an organotitanium reagent, by reaction with Ti(O-iPr)₄, followed by reaction with e.g. cyclohexanecarboxaldehyde resulted in regioselective reaction at theɑ-position to give the corresponding hydroxy sulfide: Bull. Chem. Soc. Jpn., 57, 2781 (1984). For review of allylic and benzylic carbanions substituted by heteroatoms, see: Org. React., 27, 1 (1982).