2-(phenylsulfanyl)acetonitrile

• ChemBase ID: 8851
• Molecular Formular: C8H7NS
• Molecular Mass: 149.21288
• Monoisotopic Mass: 149.02992023
• SMILES: c1(ccccc1)SCC#N
• Canonical SMILES: N#CCSc1ccccc1
• InChI: InChI=1S/C8H7NS/c9-6-7-10-8-4-2-1-3-5-8/h1-5H,7H2
• InChIKey: QMJWPWCKRKHUNY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(phenylsulfanyl)acetonitrile
• IUPAC Traditional name: acetonitrile, (phenylthio)-
• Synonyms: Phenylthioacetonitrile; 2-(phenylthio)acetonitrile; (Phenylmercapto)acetonitrile; (Phenylthio)acetonitrile; 2-(phenylsulfanyl)acetonitrile; Cyanomethyl phenyl sulfide; Phenylmercaptoacetonitrile; 苯基腈乙基硫醚; (苯硫基)乙腈

Database IDs

• CAS Number: 5219-61-4
• EC Number: 226-013-3
• MDL Number: MFCD00019831
• Beilstein Number: 2042078
• PubChem SID: 160972158; 24887416
• PubChem CID: 78891

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.8260612
• LogD (pH = 7.4): 1.8260612
• Log P: 1.8260612
• Molar Refractivity: 44.0284 cm^3
• Polarizability: 16.905497 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 146-147 °C/14 mmHg(lit.); 146-147°C/14mm; 146-147°C/14mm
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.142; 1.142 g/mL at 25 °C(lit.)
• Refractive Index: 1.5820; n20/D 1.583; n20/D 1.583(lit.)
• Hydrophobicity(logP): 1.684

Safety Information

• Storage Warning: IRRITANT, STENCH
• RTECS: AM1900000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 23-24/25; 36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• GHS Precautionary statements: P280F
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥95% (GC); 95%; 97%; 98%
• Grade: technical
• Linear Formula: C6H5SCH2CN

DETAILS

Sigma Aldrich - 79178

Other Notes
Versatile CH-acidic compound1,2; Michael additions3; Vicarious substitution of hydrogen in aryls4,5
Packaging
10 mL in glass bottle

REFERENCES

• Electron-deficient aromatics undergo vicarious nucleophilic substitution (VNS) reactions with the anion. Thus the molecule is equivalent to an acetonitrile anion synthon with thiophenate as the leaving group. For example, in the presence of solid NaOH in DMSO, nitrobenzene gives predominantly 4-nitrophenylacetonitrile, along with some of the 2-isomer: J. Org. Chem., 45, 1534 (1980).
• Electrochemical ɑ-monofluorination with Triethylamine trihydrofluoride, L14417 occurs in good yield: J. Org. Chem., 60, 3459 (1995).