Malathion

• Formula: C₁₀H₁₉O₆PS₂
• Molecular weight: 330.358
• IUPAC Standard InChI: InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3 Copy

  
• IUPAC Standard InChIKey: JXSJBGJIGXNWCI-UHFFFAOYSA-N Copy
• CAS Registry Number: 121-75-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Butanedioic acid, [(dimethoxyphosphinothioyl)thio]-, diethyl ester; Succinic acid, mercapto-, diethyl ester, S-ester with O,O-dimethyl phosphorodithioate; [(Dimethoxyphosphinothioyl)thio]butanedioic acid, diethyl ester; American Cyanamid 4,049; Carbetox; Carbofos; Carbophos; Compound 4049; Cythion; Ethiolacar; Etiol; ENT 17,034; Fosfothion; Fosfotion; Fyfanon; Insecticide No. 4049; Karbofos; Malafor; Malamar 50; Malaspray; Malathion E50; Malathion LV Concentrate; Malatol; Mercaptosuccinic acid diethyl ester, S-ester with O,O-dimethyl phosphorothioate; Mercaptothion; Moscarda; O,O-Dimethyl S-(1,2-dicarbethoxyethyl) dithiophosphate; Oleophosphothion; Ortho Malathion; Phosphothion; Prioderm; S-[1,2-Bis(carbethoxy)ethyl] O,O-dimethyl dithiophosphate; S-[1,2-Bis(ethoxycarbonyl)ethyl] O,O-dimethyl phosphorodithioate; Sadofos; Sadophos; Siptox I; Staeubol-Puder; Sumitox; SF 60; TM-4049; Zithiol; AC 26691; Carbethoxy malathion; Chemathion; Dicarboethoxyethyl O,O-dimethyl phosphorodithioate; Diethyl mercaptosuccinate, O,O-dimethyl dithiophosphate, S-ester; Diethyl mercaptosuccinate, O,O-dimethyl phosphorodithioate; Diethyl mercaptosuccinate, O,O-dimethyl thiophosphate; Diethyl mercaptosuccinic acid, S-ester of O,O-dimethyl phosphorodithioate; Diethyl 2-(dimethoxyphosphinothioylthio)succinate; Dithiophosphate de O,O-dimethyle et de S-(1,2-dicarboethoxyethyle); Emmatos; Emmatos extra; Experimental insecticide 4049; Formal; Four thousand forty-nine; Malagran; Malakill; Malamar; Malaphos; Malathione; Malathon; Malation; Malatox; Malphos; MLT; NCI-C00215; O,O-Dimethyl dithiophosphate diethylmercaptosuccinate; O,O-Dimethyl S-(1,2-dicarbethoxyethyl) phosphorodithioate; O,O-Dimethyl S-(1,2-dicarbethoxyethyl) thiothionophosphate; O,O-Dimethyl S-1,2-di(ethoxycarbamyl)ethyl phosphorothioate; O,O-Dimethyl-S-1,2-dikarbetoxylethylditiofosfat; S-(1,2-Bis(aethoxy-carbonyl)-aethyl)-O,O-dimethyl-dithiophasphat; S-(1,2-Bis(ethoxy-carbonyl)-ethyl)-O,O-dimethyl-dithiofosfaat; S-(1,2-Bis(etossi-carbonil)-etil)-O,O-dimetil-ditiofosfato; S-(1,2-Dicarbethoxyethyl) O,O-dimethyl phosphorodithioate; S-1,2-Bis(ethoxycarbonyl)ethyl-O,O-dimethyl thiophosphate; Taskil; 1,2-Di(ethoxycarbonyl)ethyl O,O-dimethyl phosphordithioate; Calmathion; Carbetovur; Celthion; Cimexan; Detmol MA; S-(1,2-Dicarbethoxyethyl) O,O-dimethyldithiophosphate; 1,2-Di(ethoxycarbonyl)ethyl O,O-dimethyl phosphorodithioate; S-(1,2-Di(ethoxycarbonyl)ethyl) dimethyl phosphorothiolothionate; Diethyl (dimethoxyphosphinothioylthio) butanedioate; Diethyl (dimethoxyphosphinothioylthio)succinate; Diethyl mercaptosuccinate S-ester with O,O-dimethyl phosphorodithioate; Diethyl mercaptosuccinic acid O,O-dimethyl phosphorodithioate; O,O-Dimethyl S-1,2-di(ethoxycarbamyl)ethyl phosphorodithioate; O,O-Dwumetylo-S-1,2-bis(karboetoksyetylo)-dwutiofosforan; EL 4049; Extermathion; Forthion; Fosfotion 550; Hilthion; Hilthion 25WDP; Kop-thion; Kypfos; Latka 4049; Malacide; Malaphele; Malasol; Malathiozoo; Maldison; Malmed; Maltox; Maltox MLT; Mercaptosuccinic acid diethyl ester; Mercaptotion; NA 2783; OMS 1; Sadofos 30; TAK; Vegfru malatox; Vetiol; Cleensheen; Derbac-M; Diethyl [(dimethoxyphosphinothoiyl)thio]butanedioate; O,O-Dimethyl-S-(1,2-di(ethoxycarbonyl)ethyl) phosphorodithioate; Organoderm; Suleo M; Gammaxine; Ovide; Radotion; Malataf; Malathion ULV; Malathyl; Malathyne; (dl) malathion
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• Information on this page:
  • Phase change data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

Henry's Law data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

IR Spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, custom temperature program

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Erdmann, Rochholz, et al., 1992
Erdmann, F.; Rochholz, G.; Schütz, H., Retention-indices on OV-1 of approximately 170 commonly used pesticides, Mikrochim. Acta, 1992, 106, 3-6, 219-226, https://doi.org/10.1007/BF01242093 . [all data]

Oyama, Sano, et al., 1987
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, 1987, 33, 5, 342-348, https://doi.org/10.1248/jhs1956.33.342 . [all data]

Lora-Tamayo, Rams, et al., 1986
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., 1986, 374, 73-85, https://doi.org/10.1016/S0378-4347(00)83254-5 . [all data]

Hall, Whitehead, et al., 1986
Hall, G.L.; Whitehead, W.E.; Mourer, C.R.; Shibamoto, T., A new gas chromatographic retention index for pesticides and related compounds, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 5, 266-271, https://doi.org/10.1002/jhrc.1240090503 . [all data]

Schepers, Wijsbeek, et al., 1982
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., 1982, 27, 1, 49-60. [all data]

Tanabe, Mitobe, et al., 2000
Tanabe, A.; Mitobe, H.; Kawata, K.; Sakai, M.; Yasuhara, A., New monitoring system for ninety pesticides and related compounds in river water by solid-phase extraction with determination by gas chromatography/mass spectrometry, J. AOAC Int., 2000, 83, 1, 61-77. [all data]

Osselton and Snelling, 1986
Osselton, M.D.; Snelling, R.D., Chromatographic Identification of Pesticides, J. Chromatogr., 1986, 368, 265-271, https://doi.org/10.1016/S0021-9673(00)91068-9 . [all data]

Mondello, Casilli, et al., 2007
Mondello, L.; Casilli, A.; Tranchida, P.Q.; Presti, M.L.; Dugo, P.; Dugo, G., Comprehensive gas chromatography coupled to mass spectrometry for the separation of pesticides in a very complex matrix, Anal. Bioanal. Chem., 2007, 389, 6, 1755-1763, https://doi.org/10.1007/s00216-007-1412-y . [all data]

Bicchi, D'Amato, et al., 1996
Bicchi, C.; D'Amato, A.; Binello, A., Identification of pesticide residues in real matrices by combining retention indices and specific multidetection responses, J. Hi. Res. Chromatogr., 1996, 19, 2, 80-84, https://doi.org/10.1002/jhrc.1240190204 . [all data]

Bicchi, D'Amato, et al., 1994
Bicchi, C.; D'Amato, A.; Orlandin, M., Identification of the constituents of a complex mixture by combined use of retention indices and specific multidetection responses, J. Hi. Res. Chromatogr., 1994, 17, 5, 335-338, https://doi.org/10.1002/jhrc.1240170510 . [all data]

TSunoda, 1986
TSunoda, N., Simultaneous determination of organophosphorous pesticides in forencis chemistry by gas-liquid chromatography with hydrogen flame ionization detector, Eisei Kagaku, 1986, 32, 2, 91-100, https://doi.org/10.1248/jhs1956.32.91 . [all data]

Marozzi, Gambaro, et al., 1982
Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 1982, 6, 4, 185-192, https://doi.org/10.1093/jat/6.4.185 . [all data]

Department of Food Safety and Welfare, 2006
Department of Food Safety, Ministry of Health; Welfare, Analytical methods for residual compositional substances of agricultural chemicals, feed aadditives, and veterinary drugs in foods, 2006, retrieved from http://www.mhlw.go.jp/english/topics/foodsafety/positivelist060228/de/060526-1a.pdf. [all data]

Kawara, Asada, et al., 2005
Kawara, K.; Asada, T.; Oikawa, K.; Tanabe, A., Multiresidue determination of pesticides in sediments by ultrasonically assisted extraction and gas chromatography/mass spectrometry, J. AOAC International, 2005, 88, 5, 1440-1451. [all data]

Zenkevich, Ostroukhova, et al., 2002
Zenkevich, I.G.; Ostroukhova, O.K.; Dolzhenko, V.I., Optimum analytical parameters for chromatographic characterization of pesticides, J. Anal. Chem. USSR (Engl. Transl.), 2002, 57, 1, 35-39. [all data]

Soderstrom, White, et al., 2001
Soderstrom, M.; White, E.; Abis, L.; Sliwakowski, M., Summary report of the eight meeting of the validation group for the updating of the central OPCW analytical database, 28-29 November 2000, CS-2001-2242, Verification Division S/239/2001, 2001, 14. [all data]

Kawata, Mukai, et al., 1996
Kawata, K.; Mukai, H.; Tanabe, H.; Yasuhara, A., Annual variation of insecticides in precipitation in rural Japan, Bull. Environ. Contam. Toxicol., 1996, 57, 6, 853-858, https://doi.org/10.1007/s001289900268 . [all data]

Tameo and Kiyos, 1991
Tameo, O.; Kiyos, I., Simultaneous determination of pesticides by capillary gas chromatography, Cannot be traslated (in Japan), 1991, 14, 2, 109-122. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Ardrey and Moffat, 1981
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., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔvapH°	Enthalpy of vaporization at standard conditions

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