ChemSpider 2D Image | (E)-3-(4-t-Butylphenylsulfonyl)-2-propenenitrile | C13H15NO2S

(E)-3-(4-t-Butylphenylsulfonyl)-2-propenenitrile

  • Molecular FormulaC13H15NO2S
  • Average mass249.329 Da
  • Monoisotopic mass249.082352 Da
  • ChemSpider ID4510087

  • Double-bond stereo - Double-bond stereo

More details:

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(2E)-3-[(4-tert-Butylphenyl)sulfonyl]acrylonitrile
(2E)-3-{[4-(2-Methyl-2-propanyl)phenyl]sulfonyl}acrylonitril [German] [ACD/IUPAC Name]
(2E)-3-{[4-(2-Methyl-2-propanyl)phenyl]sulfonyl}acrylonitrile [ACD/IUPAC Name]
(2E)-3-{[4-(2-Méthyl-2-propanyl)phényl]sulfonyl}acrylonitrile [French] [ACD/IUPAC Name]
(E)-3-(4-t-Butylphenylsulfonyl)-2-propenenitrile
196309-76-9 [RN]
2-Propenenitrile, 3-[[4-(1,1-dimethylethyl)phenyl]sulfonyl]-, (2E)- [ACD/Index Name]
MFCD01862602 [MDL number]
(2E)-3-(4-tert-butylbenzene-1-sulfonyl)prop-2-enenitrile
(2E)-3-(4-TERT-BUTYLBENZENESULFONYL)PROP-2-ENENITRILE
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Bay 11-7085 [DBID]
B5681_SIGMA [DBID]
Bay 11-7083 | [DBID]
EU-0100183 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A sulfone that is benzene substituted by [(E)-2-cyanoethenyl]sulfonyl and tert-butyl groups at position 1 and 4, respectively. It is an irreversible inhibitor of IkappaB-alpha phosphorylation in cells (IC50 = 10 muM) and prevents the activation of NF-kappaB. ChEBI CHEBI:176500

    • Bio Activity:

      Cell Biology Tocris Bioscience 1743
      Cytokine and NF-kB Signaling Tocris Bioscience 1743
      Irreversible inhibitor of TNF-?-induced I?B? phosphorylation Tocris Bioscience 1743
      Irreversible inhibitor of TNF-?-stimulated I?B? phosphorylation (IC50 ~ 10 ?M); leads to decreased NF-?B and subsequent decreased expression of adhesion molecules. Also reversibly activates MAP kinase s and stimulates apoptosis. Anti-inflammatory in vivo. Tocris Bioscience 1743
      Irreversible inhibitor of TNF-?-stimulated I?B? phosphorylation (IC50 ~ 10 ?M); leads to decreased NF-?B and subsequent decreased expression of adhesion molecules. Also reversibly activates MAP kinases and stimulates apoptosis. Anti-inflammatory in vivo. Tocris Bioscience 1743
      Irreversible inhibitor of TNF-alpha-induced IkappaBalpha phosphorylation Tocris Bioscience 1743
      Irreversible inhibitor of TNF-alpha-stimulated IkappaBalpha phosphorylation (IC50 ~ 10 muM); leads to decreased NF-kappaB and subsequent decreased expression of adhesion molecules. Also reversibly activates MAP kinases and stimulates apoptosis. Anti-inflammatory in vivo. Tocris Bioscience 1743
      NF-kB/IkB Tocris Bioscience 1743
      Signal Transduction Tocris Bioscience 1743

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.1±0.1 g/cm3
Boiling Point: 407.1±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.9 mmHg at 25°C
Enthalpy of Vaporization: 65.9±3.0 kJ/mol
Flash Point: 200.0±28.7 °C
Index of Refraction: 1.535
Molar Refractivity: 67.8±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 2.51
ACD/LogD (pH 5.5): 2.51
ACD/BCF (pH 5.5): 47.45
ACD/KOC (pH 5.5): 551.37
ACD/LogD (pH 7.4): 2.51
ACD/BCF (pH 7.4): 47.45
ACD/KOC (pH 7.4): 551.37
Polar Surface Area: 66 Å2
Polarizability: 26.9±0.5 10-24cm3
Surface Tension: 42.1±3.0 dyne/cm
Molar Volume: 217.9±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.77

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  388.46  (Adapted Stein & Brown method)
    Melting Pt (deg C):  138.46  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.14E-006  (Modified Grain method)
    Subcooled liquid VP: 1.58E-005 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  398.8
       log Kow used: 1.77 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1545.9 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Allylic/Vinyl Nitriles
       Vinyl/Allyl Sulfones

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.01E-008  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  9.378E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.77  (KowWin est)
  Log Kaw used:  -6.085  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.855
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7519
   Biowin2 (Non-Linear Model)     :   0.9160
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3537  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2694  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1561
   Biowin6 (MITI Non-Linear Model):   0.0310
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2656
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.00211 Pa (1.58E-005 mm Hg)
  Log Koa (Koawin est  ): 7.855
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00142 
       Octanol/air (Koa) model:  1.76E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0489 
       Mackay model           :  0.102 
       Octanol/air (Koa) model:  0.0014 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  10.4443 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =  11.6603 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.024 Days (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   11.008 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.004375 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     0.008750 E-17 cm3/molecule-sec [Trans-]
      Half-Life =   261.943 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =   130.971 Days (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.0756 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1093
      Log Koc:  3.039 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.663 (BCF = 4.605)
       log Kow used: 1.77 (estimated)

 Volatilization from Water:
    Henry LC:  2.01E-008 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:   4.6E+004  hours   (1917 days)
    Half-Life from Model Lake : 5.019E+005  hours   (2.091E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               2.08  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.99  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.187           24.5         1000       
   Water     28.8            900          1000       
   Soil      71              1.8e+003     1000       
   Sediment  0.0879          8.1e+003     0          
     Persistence Time: 1.17e+003 hr

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