ChemSpider 2D Image | Fumaric acid | C4H4O4

Fumaric acid

  • Molecular FormulaC4H4O4
  • Average mass116.072 Da
  • Monoisotopic mass116.010956 Da
  • ChemSpider ID10197150
  • Double-bond stereo - Double-bond stereo


More details:



Featured data source



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

Fumaric acid [Wiki]
(2E)-2-Butendisäure [German] [ACD/IUPAC Name]
(2E)-2-Butenedioic acid [ACD/IUPAC Name]
(2E)-But-2-enedioic acid
(E)-1,2-Ethylenedicarboxylic acid
(E)-2-Butenedioic acid
(E)-Butenedioic acid
1,2-Ethenedicarboxylic acid, trans-
110-17-8 [RN]
2-Butenedioic acid [ACD/IUPAC Name]
More...

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

CHEBI:18012 [DBID]
03761_FLUKA [DBID]
240745_ALDRICH [DBID]
AI3-24236 [DBID]
AIDS008707 [DBID]
AIDS-008707 [DBID]
bmse000083 [DBID]
BRN 0605763 [DBID]
C00122 [DBID]
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  • Experimental Physico-chemical Properties
    • Experimental Melting Point:

      298-300 °C (Literature, Sublimes) Indofine [020723]
      299 °C (Sublimes) Alfa Aesar
      230 °C (Decomposes) Oxford University Chemical Safety Data (No longer updated) More details
      132-136 °C Alfa Aesar [A14596]
      138 °C Jean-Claude Bradley Open Melting Point Dataset 14807
      130.5 °C Jean-Claude Bradley Open Melting Point Dataset 25955
      299.5 °C Jean-Claude Bradley Open Melting Point Dataset 28127, 28128
      287 °C Jean-Claude Bradley Open Melting Point Dataset 28127, 28128
      134 °C Jean-Claude Bradley Open Melting Point Dataset 7427
      299 °C (Sublimes) Alfa Aesar A10976
    • Experimental Boiling Point:

      165 °C (Sublimes) Oxford University Chemical Safety Data (No longer updated) More details
    • Experimental Flash Point:

      230 °C Oxford University Chemical Safety Data (No longer updated) More details
      273 °C Alfa Aesar
      127 °C Alfa Aesar [A14596]
      273 °C Alfa Aesar
      273 °F (133.8889 °C) Alfa Aesar A10976
    • Experimental Gravity:

      1.59 g/mL Alfa Aesar [A14596]
      1.625 g/mL Alfa Aesar A10976
  • Miscellaneous
    • Appearance:

      white powder or colourless crystals Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable at room temperature. Decomposes at around 230 C. Incompatible with strong oxidizing agents, bases, reducing agents. Combustible. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 9300 mg kg-1 , IPR-MUS LD50 200 mg kg-1, SKN-RBT LD50 20 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      22-36/37/38-43 Alfa Aesar [A14596]
      24-26-28-37-46 Alfa Aesar [A14596]
      26 Alfa Aesar A10976
      36 Alfa Aesar A10976
      H319 Alfa Aesar A10976
      IRRITANT Matrix Scientific 098686
      Minimize exposure. Oxford University Chemical Safety Data (No longer updated) More details
      P305+P351+P338 Alfa Aesar A10976
      Warning Alfa Aesar A10976
      WARNING: Irritates skin and eyes Alfa Aesar A10976
      Xi Abblis Chemicals AB1002616
  • Gas Chromatography

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

Density: 1.5±0.1 g/cm3
Boiling Point: 355.5±25.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 66.0±6.0 kJ/mol
Flash Point: 183.0±19.7 °C
Index of Refraction: 1.526
Molar Refractivity: 23.8±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: -0.01
ACD/LogD (pH 5.5): -2.74
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -4.72
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 75 Å2
Polarizability: 9.4±0.5 10-24cm3
Surface Tension: 67.7±3.0 dyne/cm
Molar Volume: 77.4±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) =  0.05
    Log Kow (Exper. database match) =  -0.48
       Exper. Ref:  Sangster (1994)
    Log Kow (Exper. database match) =  0.46
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  285.25  (Adapted Stein & Brown method)
    Melting Pt (deg C):  84.12  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.43E-012  (Modified Grain method)
    MP  (exp database):  287 dec deg C
    BP  (exp database):  522 deg C
    VP  (exp database):  1.54E-04 mm Hg at 25 deg C
    Subcooled liquid VP: 0.0601 mm Hg (25 deg C, exp database VP )

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1.042e+005
       log Kow used: 0.46 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  4.41e+005 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
     Water Sol (Exper. database match) =  7000 mg/L (25 deg C)
        Exper. Ref:  US EPA (1981)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  3.2661e+005 mg/L
    Wat Sol (Exper. database match) =  441000.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)
    Wat Sol (Exper. database match) =  7000.00
       Exper. Ref:  US EPA (1981)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.35E-012  atm-m3/mole
   Group Method:   8.48E-014  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.382E-017 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.46  (exp database)
  Log Kaw used:  -10.258  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.718
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8377
   Biowin2 (Non-Linear Model)     :   0.9338
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   3.6719  (days-weeks  )
   Biowin4 (Primary Survey Model) :   4.4514  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.7415
   Biowin6 (MITI Non-Linear Model):   0.8177
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  1.0626
 Ready Biodegradability Prediction:   YES

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

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  8.01 Pa (0.0601 mm Hg)
  Log Koa (Koawin est  ): 10.718
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.74E-007 
       Octanol/air (Koa) model:  0.0128 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1.35E-005 
       Mackay model           :  2.99E-005 
       Octanol/air (Koa) model:  0.506 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   7.9490 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant =   8.8800 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =    1.346 Days (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =    1.205 Days (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.087500 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =     0.175000 E-17 cm3/molecule-sec [Trans-]
      Half-Life =    13.097 Days (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =     6.549 Days (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 2.17E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6.314
      Log Koc:  0.800 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 0.46 (expkow database)

 Volatilization from Water:
    Henry LC:  8.48E-014 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 7.438E+009  hours   (3.099E+008 days)
    Half-Life from Model Lake : 8.115E+010  hours   (3.381E+009 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       0.0702          29.3         1000       
   Water     33.4            208          1000       
   Soil      66.4            416          1000       
   Sediment  0.0594          1.87e+003    0          
     Persistence Time: 388 hr




                    

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