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Permethrin

Molecular FormulaC₂₁H₂₀Cl₂O₃
Average mass391.288 Da
Monoisotopic mass390.078949 Da
ChemSpider ID36845

More details:

Names and Synonyms
Database ID(s)

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

Permethrin [Wiki]

(±)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

(3-Phenoxyphenyl)methyl (±)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

(3-Phenoxyphenyl)methyl 3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarboxylate

(3-Phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

(3-Phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

[3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

258-067-9 [EINECS]

3-(2,2-Dichloroéthényl)-2,2-diméthylcyclopropanecarboxylate de 3-phénoxybenzyle [French]

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

5510 [DBID]

5765325 [DBID]

Caswell No. 652BB [DBID]

FMC 33297 [DBID]

FMC 41655 [DBID]

HSDB 6790 [DBID]

JF 7065 [DBID]

NIA 33297 [DBID]

NRDC 143 [DBID]

OMS 1821 [DBID]

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Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon
Predicted - Mcule

Experimental Physico-chemical Properties

Experimental Melting Point:

Experimental Boiling Point:

200 °C / 1 mmHg OU Chemical Safety Data (No longer updated) More details
Experimental LogP:

7.15 Vitas-M STL135986
Experimental Solubility:

DMSO 40 mg/ml; Ethanol 20 mg/ml MedChem Express http://www.medchemexpress.com/Sulfacetamide-sodium-monohydrate.html, HY-B0887

Miscellaneous

Appearance:

colourless crystals (but the technical product OU Chemical Safety Data (No longer updated) More details
Stability:

Stable. Incompatible with strong oxidising agents. OU Chemical Safety Data (No longer updated) More details

Retention Index (Normal Alkane):

2631.8 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Heat rate: 5 K/min; Start T: 50 C; End T: 280 C; Start time: 4 min; CAS no: 51877748; Active phase: CP-Sil5 CB MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Dalluge, J.; van Rijn, M.; Beens, J.; Vreuls, R.J.J.; Brinkman, U.A.Th., Comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometric detection applied to the determination of pesticides in food extracts, J. Chromatogr. A, 965, 2002, 207-217.) NIST Spectra nist ri

2623.6 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.2 mm; Column length: 12 m; Column type: Capillary; Heat rate: 18 K/min; Start T: 60 C; End T: 265 C; Start time: 1 min; CAS no: 51877748; Active phase: HP-1; Carrier gas: He; Phase thickness: 0.33 um; Data type: Normal alkane RI; Authors: Liao, W.; Joe, T.; Cusick, W.G., Multiresidue screening method for fresh fruits and vegetables with gas chromatographic/mass spectrometric detection, J. Ass. Offic. Anal. Chem, 74(3), 1991, 554-565.) NIST Spectra nist ri

2656.1 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 1.1 m; Column type: Packed; Heat rate: 8.5 K/min; Start T: 50 C; End T: 300 C; CAS no: 51877748; Active phase: OV-101; Carrier gas: N2; Substrate: Chromosorb W HP; Data type: Normal alkane RI; Authors: Saxton, W.L., Emergence temperature indices and relative retention times of pesticides and industrial chemicals determined by linear programmed temperature gas chromatography, J. Chromatogr., 393, 1987, 175-194.) NIST Spectra nist ri

2659.6 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 70C(2min) =>25C/min =>150C=>3C/min => 200C=> 8C/min =>280C(10min); CAS no: 51877748; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Wong, J.W.; Webster, M.G.; Bezabeh, D.Z.; Hengel, M.J.; Ngim, K.K.; Krynitsky, A.J.; Ebeler, S.E., Multiresidue determination of pesticides in malt beverages by capillary gas chromatography with mass spectrometry and selected ion monitoring, J. Agric. Food Chem., 52, 2004, 6361-6372.) NIST Spectra nist ri

2620.5 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 57C(2min) => 40C/min=> 130C=> 5C/min=> 200C=> 7C/min=> 270C(10min); CAS no: 51877748; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.2 um; Data type: Normal alkane RI; Authors: Haib, J.; Hofer, I.; Renaud, J.-M., Analysis of multiple pesticide residues in tobacco using pressurized liquid extraction, automated solid-phase extraction clean-up and gas chromatography-tandem mass spectrometry, J. Chromatogr. A, 1020, 2003, 173-187.) NIST Spectra nist ri

2670.9 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 50 C (1.13 min) ^ 30 C/min -> 150 C ^ 3 C/min -> 205 C ^ 10 C/min -> 250 C (20 min); CAS no: 51877748; Active phase: HP-5; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Cook, J.; Engel, M.; Wylie, P.; Quimby, B., Multiresidue screening of pesticides in foods using retention time locking, GC-AED, database search, and GC/MS identification, J. AOAC Int., 82(2), 1999, 313-326.) NIST Spectra nist ri

2697.6 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 6 K/min; Start T: 60 C; End T: 260 C; End time: 12 min; CAS no: 51877748; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Mogadati, P.; Louis, J.B.; Rosen, J.D., Multiresidue determination of pesticides in high-organic-content soils by solid-phase extraction and gas chromatography/mass spectrometry, J. AOAC Int., 82(3), 1999, 705-715.) NIST Spectra nist ri

2678.3 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 30 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 100 C; End T: 275 C; End time: 2 min; Start time: 5 min; CAS no: 51877748; Active phase: RTX-5; Carrier gas: He; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Restek, Restek International, 1999 Product Guide, 1(1), 1999, 578-591, In original 578-591.) NIST Spectra nist ri

2658.8 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 2.5 mm; Column length: 30 m; Column type: Capillary; Description: 60 0C (1 min) ^ 15 0C/min -> 180 0C (4 min) ^ 5 0C/min -> 205 0C ^ 20 0C/min -> 295 0C (5 min); overall run time is 27.5 min; CAS no: 51877748; Active phase: HP-5; Carrier gas: He; Phase thickness: 2.5 um; Data type: Normal alkane RI; Authors: Johnson, P.D.; Rimmer, D.A.; Brown, R.H., Adaptation and application of a multi-residue method for the determination of a range of pesticides, including phenoxy acid herbicides in vegetation, ased on high-resolution gel permeation chromatographic clean-up and gas chromatographic analysis with mass-selective detection, J. Chromatogr. A, 765, 1997, 3-11.) NIST Spectra nist ri

2654.8 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.2 mm; Column length: 29 m; Column type: Capillary; Description: 80 C (1 min) ^ 6 C/min -> 200 C (3 min) ^ 6 C/min -> 260 C (8 min); CAS no: 51877748; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Papadopoulou-Mourkidou, E.; Patsias, J.; Kotopoulou, A., Determination of pesticides in soils by gas chromatography-ion trap mass spectrometry, J. AOAC Int., 80(2), 1997, 447-454.) NIST Spectra nist ri

2653.5 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 80(1)-6^ ->200(3)-6^ -> 260(10); CAS no: 51877748; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Patsias, J.; Papadopoulou-Mourkidou, E., Rapid method for the analysis of a variety of chemical classes of pesticides in surface and ground waters by off-line solid phase extraction and gas chromatography-ion trap mass spectrometry, J. Chromatogr. A, 740, 1996, 83-98.) NIST Spectra nist ri

2666.8 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 30 m; Column type: Capillary; Heat rate: 2.8 K/min; Start T: 140 C; End T: 270 C; End time: 1 min; Start time: 2 min; CAS no: 51877748; Active phase: DB-5; Carrier gas: He; Phase thickness: 1.5 um; Data type: Normal alkane RI; Authors: Lopez-Avila, V.; Benedicto, J.; Baldin, E.; Beckert, W.F., Analysis of classes of compounds of environmental concern: III. Organochlorine pesticides, J. Hi. Res. Chromatogr., 15, 1992, 319-328.) NIST Spectra nist ri

Retention Index (Linear):

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

Density:	1.3±0.1 g/cm³
Boiling Point:	465.9±45.0 °C at 760 mmHg
Vapour Pressure:	0.0±1.2 mmHg at 25°C
Enthalpy of Vaporization:	72.8±3.0 kJ/mol
Flash Point:	159.4±27.7 °C
Index of Refraction:	1.616
Molar Refractivity:	105.7±0.3 cm³
#H bond acceptors:	3
#H bond donors:	0
#Freely Rotating Bonds:	7
#Rule of 5 Violations:	1

ACD/LogP:	7.15
ACD/LogD (pH 5.5):	6.47
ACD/BCF (pH 5.5):	48634.18
ACD/KOC (pH 5.5):	78794.31
ACD/LogD (pH 7.4):	6.47
ACD/BCF (pH 7.4):	48634.18
ACD/KOC (pH 7.4):	78794.31
Polar Surface Area:	36 Å²
Polarizability:	41.9±0.5 10^-24cm³
Surface Tension:	50.5±3.0 dyne/cm
Molar Volume:	302.5±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) =  7.43
    Log Kow (Exper. database match) =  6.50
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  437.64  (Adapted Stein & Brown method)
    Melting Pt (deg C):  164.97  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.26E-007  (Modified Grain method)
    MP  (exp database):  34 deg C
    BP  (exp database):  220 @ 0.05 mm Hg deg C
    VP  (exp database):  2.18E-08 mm Hg at 25 deg C
    Subcooled liquid VP: 2.68E-008 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):  0.009747
       log Kow used: 6.50 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  0.006 mg/L (20 deg C)
        Exper. Ref:  USDA PESTICIDE PROP DATABASE

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.0023788 mg/L
    Wat Sol (Exper. database match) =  0.01
       Exper. Ref:  USDA PESTICIDE PROP DATABASE

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Vinyl/Allyl Halides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.88E-007  atm-m3/mole
   Group Method:   Incomplete
   Exper Database: 1.87E-06  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  4.363E-005 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.50  (exp database)
  Log Kaw used:  -4.117  (exp database)
      Log Koa (KOAWIN v1.10 estimate):  10.617
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5887
   Biowin2 (Non-Linear Model)     :   0.5375
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8801  (months      )
   Biowin4 (Primary Survey Model) :   3.2395  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2070
   Biowin6 (MITI Non-Linear Model):   0.0060
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0206
 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):  3.57E-006 Pa (2.68E-008 mm Hg)
  Log Koa (Koawin est  ): 10.617
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.84 
       Octanol/air (Koa) model:  0.0102 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.968 
       Mackay model           :  0.985 
       Octanol/air (Koa) model:  0.448 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  22.8850 E-12 cm3/molecule-sec
      Half-Life =     0.467 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     5.609 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.023261 E-17 cm3/molecule-sec
      Half-Life =    49.268 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.977 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.784E+005
      Log Koc:  5.251 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  4.021E-002  L/mol-sec
  Kb Half-Life at pH 8:     199.518  days   
  Kb Half-Life at pH 7:       5.463  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.655 (BCF = 451.9)
       log Kow used: 6.50 (expkow database)

 Volatilization from Water:
    Henry LC:  1.87E-006 atm-m3/mole  (Henry experimental database)
    Half-Life from Model River:      621.4  hours   (25.89 days)
    Half-Life from Model Lake :       6944  hours   (289.3 days)

 Removal In Wastewater Treatment:
    Total removal:              93.43  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    92.66  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       0.101           11.1         1000       
   Water     1.95            1.44e+003    1000       
   Soil      32.7            2.88e+003    1000       
   Sediment  65.3            1.3e+004     0          
     Persistence Time: 4.38e+003 hr

Click to predict properties on the Chemicalize site

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Permethrin

More details:

Experimental Melting Point:

Experimental Boiling Point:

Experimental LogP:

Experimental Solubility:

Appearance:

Stability:

Toxicity:

Safety:

Chemical Class:

Bio Activity:

Retention Index (Kovats):

Retention Index (Normal Alkane):

Retention Index (Linear):

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