ChemSpider 2D Image | cyclobarbital | C12H16N2O3

cyclobarbital

  • Molecular FormulaC12H16N2O3
  • Average mass236.267 Da
  • Monoisotopic mass236.116089 Da
  • ChemSpider ID5632

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0M8A98AD9H
1394
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-cyclohexen-1-yl)-5-ethyl- [ACD/Index Name]
200-138-3 [EINECS]
205-610-2 [EINECS]
5-(1-Cyclohexen-1-yl)-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione [ACD/IUPAC Name]
5-(1-Cyclohexén-1-yl)-5-éthyl-2,4,6(1H,3H,5H)-pyrimidinetrione [French] [ACD/IUPAC Name]
5-(1-Cyclohexen-1-yl)-5-ethyl-2,4,6(1H,3H,5H)-pyrimidintrion [German] [ACD/IUPAC Name]
5-(Cyclohex-1-en-1-yl)-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trione
52-31-3 [RN]
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  • Experimental Physico-chemical Properties
  • Gas Chromatography
    • Retention Index (Kovats):

      2022 (estimated with error: 89) NIST Spectra mainlib_231559, replib_379327, replib_246347, replib_42309, replib_246338
      1970 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; Start T: 200 C; CAS no: 52313; Active phase: OV-101; Carrier gas: N2; Substrate: Chromosorb G AW DMCS (80-100 mesh); Data type: Kovats RI; Authors: Moller, M.R., Comparability of retention indices of polar substances at elevated temperatures, Chromatographia, 9(7), 1976, 311-314., Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column type: Packed; Start T: 200 C; CAS no: 52313; Active phase: OV-1; Data type: Kovats RI; Authors: Berninger, H.; Moller, M.R., Retentionsindices zur gaschromatographischen Identifizierung von Arzneimitteln, Arch. Toxicol., 37, 1977, 295-305., Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Packed; Heat rate: 30 K/min; Start T: 100 C; End T: 310 C; End time: 5 min; Start time: 3 min; CAS no: 52313; Active phase: SE-30; Carrier gas: N2; Data type: Kovats RI; Authors: Maurer, H.H., Identification and differentiation of barbiturates, other sedative-hypnotics and their metabolites in urine integrated in a general screening procedure using computerized gas chromatography-mass spectrometry, J. Chromatogr., 530, 1990, 307-326.) NIST Spectra nist ri
      1947 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.22 mm; Column length: 25 m; Column type: Capillary; Start T: 200 C; CAS no: 52313; Active phase: BP-1; Carrier gas: N2; Phase thickness: 0.25 um; Data type: Kovats RI; Authors: Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 32(6), 1987, 1574-1586., Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.53 mm; Column length: 30 m; Column type: Capillary; Start T: 200 C; CAS no: 52313; Active phase: DB-1; Carrier gas: N2; Phase thickness: 1.5 um; Data type: Kovats RI; Authors: Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 32(6), 1987, 1574-1586.) NIST Spectra nist ri
      1955 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.53 mm; Column length: 25 m; Column type: Capillary; Start T: 200 C; CAS no: 52313; Active phase: BP-1; Carrier gas: N2; Phase thickness: 1 um; Data type: Kovats RI; Authors: Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 32(6), 1987, 1574-1586.) NIST Spectra nist ri
      1973 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column diameter: 0.20 mm; Column length: 25 m; Column type: Capillary; Start T: 250 C; CAS no: 52313; Active phase: SPB-1; Carrier gas: He; Data type: Kovats RI; Authors: Lora-Tamayo, C.; Rams, M.A.; Chacon, J.M.R., Gas Chromatographic Data for 187 Nitrogen- or Phosphorus-Containing Drugs and Metabolites of Toxicological Interest Analysed on Methyl Silicone Capillary Columns, J. Chromatogr., 374, 1986, 73-85.) NIST Spectra nist ri
      1950 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.49 mm; Column length: 25 m; Column type: Capillary; Heat rate: 8 K/min; Start T: 100 C; End T: 275 C; End time: 15 min; Start time: 2 min; CAS no: 52313; Active phase: SE-30; Phase thickness: 1.14 um; Data type: Kovats RI; Authors: Schepers, P.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A., Applicability of capillary gas chromatography to substance identification in toxicology by means of retention indices, J. Forensic Sci., 27(1), 1982, 49-60.) NIST Spectra nist ri
      1952 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.22 mm; Column length: 12 m; Column type: Capillary; Heat rate: 8 K/min; Start T: 120 C; End T: 300 C; End time: 12 min; Start time: 2 min; CAS no: 52313; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.45 um; Data type: Kovats RI; Authors: Schepers, P.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A., Applicability of capillary gas chromatography to substance identification in toxicology by means of retention indices, J. Forensic Sci., 27(1), 1982, 49-60.) NIST Spectra nist ri
      1945 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column type: Packed; Start T: 200 C; CAS no: 52313; Active phase: SE-30; Data type: Kovats RI; Authors: Stead, A.H.; Gill, R.; Evans, A.T.; Moffat, A.C., Predictions of gas chromatographic retention characteristics of barbiturates from molecular structure, J. Chromatogr., 234, 1982, 277-283.) NIST Spectra nist ri
      1980 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; CAS no: 52313; Active phase: OV-1; Carrier gas: N2; Substrate: Chromosorb G, AW-DMCS; Data type: Kovats RI; Authors: Berninger, H.; Grunnagel, R.; Mall, S.; Moller, M.R., Gas chromatographic identification of unknown substances from body fluids by menas of retention indices, Beitr. Gerichtl. Med., 33, 1975, 185-191., Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; CAS no: 52313; Active phase: OV-101; Carrier gas: N2; Substrate: Chromosorb W; Data type: Kovats RI; Authors: McLinden, V.J.; Stenhouse, A.M., A chromatography system for drug identification, Forensic Sci. Int., 13, 1979, 71-79.) NIST Spectra nist ri
      1953 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 200 C; CAS no: 52313; Active phase: OV-1; Substrate: Chromosorb G; Data type: Kovats RI; Authors: Dubsky, H.; Hana, K.; Komarkova, M.; Rittich, B., Pouziti kovatsovych indexu pri toxikologickych analysach, Chem. Listy, 72, 1978, 980-984.) NIST Spectra nist ri
      1963 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; Start T: 180 C; CAS no: 52313; Active phase: OV-1; Substrate: Chromosorb G; Data type: Kovats RI; Authors: Dubsky, H.; Hana, K.; Komarkova, M.; Rittich, B., Pouziti kovatsovych indexu pri toxikologickych analysach, Chem. Listy, 72, 1978, 980-984.) NIST Spectra nist ri
      1960 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; Start T: 200 C; CAS no: 52313; Active phase: OV-101; Carrier gas: N2; Substrate: Chromosorb G AW DMCS (80-100 mesh); Data type: Kovats RI; Authors: Moller, M.R., Comparability of retention indices of polar substances at elevated temperatures, Chromatographia, 9(7), 1976, 311-314.) NIST Spectra nist ri
      1985 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; CAS no: 52313; Active phase: OV-1; Carrier gas: N2; Substrate: Chromosorb G, AW-DMCS; Data type: Kovats RI; Authors: Berninger, H.; Grunnagel, R.; Mall, S.; Moller, M.R., Gas chromatographic identification of unknown substances from body fluids by menas of retention indices, Beitr. Gerichtl. Med., 33, 1975, 185-191.) NIST Spectra nist ri
    • Retention Index (Normal Alkane):

      1946 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Capillary; Start T: 100 C; End T: 300 C; CAS no: 52313; Active phase: BP-1; Data type: Normal alkane RI; Authors: MHA, Directorate of ForensicScience., Forensic Toxicology, 9999.) NIST Spectra nist ri
      1970 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.53 mm; Column length: 10 m; Column type: Capillary; Description: 100 0C (2 min) ^ 20 0C/min -> 180 0C ^ 7.5 0C/min -> 280 0C (6 min); CAS no: 52313; Active phase: CP Sil 5 CB; Phase thickness: 5.2 um; Data type: Normal alkane RI; Authors: Bogusz, M.; Bialka, J.; Gierz, J.; Klys, M., Use of short, wide-bore capillary columns in GC toxicological screening, J. Anal. Toxicol., 10(4), 1986, 135-138., Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Capillary; CAS no: 52313; Active phase: HP-1; Carrier gas: Helium; Data type: Normal alkane RI; Authors: Grigor'ev, A.M.; Bozhko, E.S.; Rudakova, L.V., Use of correlation between retention indices on low-polarity phases for screening comp-lex mixtures by gas chromatography-mass spectrometry, Rus. J. Anal. Chem., 64(2), 2009, 140-143, In original 156-159.) NIST Spectra nist ri
      1960 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.53 mm; Column length: 10 m; Column type: Capillary; CAS no: 52313; Active phase: CP Sil 5 CB; Phase thickness: 5.2 um; Data type: Normal alkane RI; Authors: Bogusz, M.; Bialka, J.; Gierz, J.; Klys, M., Use of short, wide-bore capillary columns in GC toxicological screening, J. Anal. Toxicol., 10(4), 1986, 135-138.) NIST Spectra nist ri
      1940 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Heat rate: 2.5 K/min; Start T: 120 C; End T: 200 C; CAS no: 52313; Active phase: OV-1; Substrate: Gas Chrom P; Data type: Normal alkane RI; Authors: Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 6, 1982, 185-192.) NIST Spectra nist ri
      1963 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Other; CAS no: 52313; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri
      1950 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; Start T: 200 C; CAS no: 52313; Active phase: OV-101; Carrier gas: N2; Substrate: Chromosorb G AW DMCS (80-100 mesh); Data type: Normal alkane RI; Authors: Moller, M.R., Comparability of retention indices of polar substances at elevated temperatures, Chromatographia, 9(7), 1976, 311-314.) NIST Spectra nist ri
      1932.8 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.34 mm; Column length: 18 m; Column type: Capillary; Heat rate: 25 K/min; Start T: 100 C; End T: 275 C; End time: 5 min; Start time: 2 min; CAS no: 52313; Active phase: CP Sil 8 CB; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: de Baere, S.M.; Lambert, W.E.; van Bocxlaer, J.F.; de Leenheer, A.P., Quantitative gas chromatographic analysis of 3-cyano-3,3-diphenylpropionic acid, the acidic metabolite of bezitramide (Burgodin), in urine, J. Anal. Toxicol., 20, 1996, 159-164.) NIST Spectra nist ri
      1988.1 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 25 m; Column type: Capillary; Description: 70 0C (0.7 min) ^ 20 0C/min -> 140 0C ^ 10 0C/min -> 280 0C (4 min); CAS no: 52313; Active phase: NB-54; Carrier gas: He; Phase thickness: 0.10 um; Data type: Normal alkane RI; Authors: Ojanpera, I.; Rasanen, I.; Vuori, E., Automated quantitative screening for acidic and neutral drugs in whole blood by dual-column capillary gas chromatography, J. Anal. Toxicol., 15, 1991, 204-208.) NIST Spectra nist ri
    • Retention Index (Linear):

      1963 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.53 mm; Column length: 10 m; Column type: Capillary; CAS no: 52313; Active phase: CP Sil 5 CB; Carrier gas: He; Phase thickness: 5.0 um; Data type: Linear RI; Authors: Aderjan, R.; Bogusz, M., Nitroalkanes as a multidetector retention index scale for drug identification in gas chromatography, J. Chromatogr., 454, 1988, 345-351.) NIST Spectra nist ri
      1967 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.53 mm; Column length: 10 m; Column type: Capillary; Description: 100 0C (2 min ) ^ 15 0C/min -> 200 0C ^ 10 0C/min -> 300 0C (8 min hold); CAS no: 52313; Active phase: CP Sil 5 CB; Carrier gas: He; Phase thickness: 5.0 um; Data type: Linear RI; Authors: Aderjan, R.; Bogusz, M., Nitroalkanes as a multidetector retention index scale for drug identification in gas chromatography, J. Chromatogr., 454, 1988, 345-351.) NIST Spectra nist ri
      1936 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.53 mm; Column length: 12 m; Column type: Capillary; Heat rate: 6 K/min; Start T: 120 C; End T: 250 C; CAS no: 52313; Active phase: CBP-1; Carrier gas: N2; Data type: Linear RI; Authors: Oyama, N.; Sano, T.; Syoyama, M.; Maeda, K., Studies on systematic analysis of poisonous compounds in forensic chemistry. II. Application of capillary column gas chromatography to substance identification by means of retention indices, Eisei Kagaku, 33(5), 1987, 342-348.) NIST Spectra nist ri

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.527
Molar Refractivity: 60.1±0.3 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 1.62
ACD/LogD (pH 5.5): 1.67
ACD/BCF (pH 5.5): 10.87
ACD/KOC (pH 5.5): 191.86
ACD/LogD (pH 7.4): 1.58
ACD/BCF (pH 7.4): 8.84
ACD/KOC (pH 7.4): 156.09
Polar Surface Area: 75 Å2
Polarizability: 23.8±0.5 10-24cm3
Surface Tension: 44.2±3.0 dyne/cm
Molar Volume: 195.4±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) =  2.30
    Log Kow (Exper. database match) =  1.77
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  563.32  (Adapted Stein & Brown method)
    Melting Pt (deg C):  242.18  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.94E-011  (Modified Grain method)
    MP  (exp database):  173 deg C
    Subcooled liquid VP: 6.61E-010 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):  866.5
       log Kow used: 1.77 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1600 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1097.8 mg/L
    Wat Sol (Exper. database match) =  1600.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Imides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.13E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.960E-015 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.77  (exp database)
  Log Kaw used:  -10.678  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.448
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4511
   Biowin2 (Non-Linear Model)     :   0.1121
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4649  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3534  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2118
   Biowin6 (MITI Non-Linear Model):   0.0778
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.1053
 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):  8.81E-008 Pa (6.61E-010 mm Hg)
  Log Koa (Koawin est  ): 12.448
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  34 
       Octanol/air (Koa) model:  0.689 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  0.982 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  97.8336 E-12 cm3/molecule-sec
      Half-Life =     0.109 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.312 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.393750 E-17 cm3/molecule-sec
      Half-Life =     0.155 Days (at 7E11 mol/cm3)
      Half-Life =      3.720 Hrs
   Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  245.6
      Log Koc:  2.390 

 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 = 4.602)
       log Kow used: 1.77 (expkow database)

 Volatilization from Water:
    Henry LC:  5.13E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.754E+009  hours   (7.31E+007 days)
    Half-Life from Model Lake : 1.914E+010  hours   (7.974E+008 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       0.00174         1.54         1000       
   Water     27.6            900          1000       
   Soil      72.3            1.8e+003     1000       
   Sediment  0.0844          8.1e+003     0          
     Persistence Time: 1.29e+003 hr




                    

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