Waheed, N., Abdulaziz, N., Hammodi, S., Mustafa, Y. (2023). Thionyl Chloride: A Catalyst of Synthetic Chemical Interest. , 20(2), 111-125. doi: 10.33899/iphr.2023.142271.1053
Noor Ahmed Waheed; Noora Thamer Abdulaziz; Sawsan Hasan Hammodi; Yasser Fakri Mustafa. "Thionyl Chloride: A Catalyst of Synthetic Chemical Interest". , 20, 2, 2023, 111-125. doi: 10.33899/iphr.2023.142271.1053
Waheed, N., Abdulaziz, N., Hammodi, S., Mustafa, Y. (2023). 'Thionyl Chloride: A Catalyst of Synthetic Chemical Interest', , 20(2), pp. 111-125. doi: 10.33899/iphr.2023.142271.1053
Waheed, N., Abdulaziz, N., Hammodi, S., Mustafa, Y. Thionyl Chloride: A Catalyst of Synthetic Chemical Interest. , 2023; 20(2): 111-125. doi: 10.33899/iphr.2023.142271.1053

Thionyl Chloride: A Catalyst of Synthetic Chemical Interest

Iraqi Journal of Pharmacy
Volume 20, Issue 2, December 2023, Pages 111-125    PDF (713.19 K)
Document Type: Review Paper
DOI: 10.33899/iphr.2023.142271.1053
Authors
Noor Ahmed Waheed1; Noora Thamer Abdulaziz* 2; Sawsan Hasan Hammodi1; Yasser Fakri Mustafa1
1Department of Pharmaceutical Chemistry, College of Pharmacy, University of Mosul, Mosul, Iraq
2Department of Pharmaceutics, College of Pharmacy, University of Mosul, Mosul, Iraq
Abstract
Background: Particularly developed ingredients that are easily manufactured and utilized for additional exploitation are used in organic synthetic chemistry. Thionyl chloride serves as a significant illustration of such an ingredient. The usefulness of which has been discussed in a huge number of peer-reviewed papers. Aim: The literature that has been released since the previous assessment in 1980, which mainly focused on the responses of active methylene compounds, is where this review places its focus. In the present overview, we also discuss O- and N-nucleophiles. For the most part, patents have been disregarded in this analysis in order to keep it feasible. Conclusion: The authors concluded that SOCl2 has a variety of behaviors, including the ability to function as an initiator or a reactant, which makes it essential for the synthesis of many chemically reactive intermediates and final products. Additionally, SOCl2 can speed up and reduce the duration of traditionally long reactions, thereby raising its importance.
Keywords
Thionyl chloride; Coupling reaction; Chalcone; Amine; Alcohol
References
  1. Zhou M, Goldman AS. Chlorination of (Phebox)Ir(mesityl)(OAc) by thionyl chloride. Molecules 2015;20(6):10122–30.
  2. Khalil RR, Mustafa YF. Phytochemical, antioxidant and antitumor studies of coumarins extracted from Granny Smith apple seeds by different methods. Systematic Reviews in Pharmacy 2020;11(2):57–63.
  3. Mustafa Y, Waheed S, Jasim S, Jebir R, Ismael R, Qutachi O. A Narrative Review of Benzo-Fused Coumarins, Shedding Light on Their Medicinal Activities. Iraqi Journal of Pharmacy 2023;20(1):7–16.
  4. Arulkumaran R, Vijayakumar S, Sundararajan R, Sakthinathan SP, Kamalakkannan D, Suresh R, et al. Thionylchloride Catalyzed Aldol Condensation: Synthesis, Spectral Correlation and Antibacterial Activities of some 3,5-Dichloro-2-Hydroxyphenyl Chalcones. International Letters of Chemistry, Physics and Astronomy 2013;4:17–38.
  5. Mohammed ET, Mustafa YF. Coumarins from Red Delicious apple seeds: Extraction, phytochemical analysis, and evaluation as antimicrobial agents. Systematic Reviews in Pharmacy 2020;11(2):64–70.
  6. Mustafa YF. Harmful Free Radicals in Aging: A Narrative Review of Their Detrimental Effects on Health. Indian Journal of Clinical Biochemistry 2023;
  7. Hu A, Zhang A, Ding L, Lei X, Zhang L. Simple and convenient synthesis of 1,3,5-triarylbenzenes from ketones. Journal of Chemical Research 2007;(12):720–1.
  8. Oglah MK, Mustafa YF. Curcumin analogs: synthesis and biological activities. Medicinal Chemistry Research 2020;29(3):479–86.
  9. Jebir RM, Mustafa YF. Natural coumarin-lead compounds: A review of their medicinal potentials. Iraqi Journal of Pharmacy 2021;18(2):139–61.
  10. Waheed SA, Mustafa YF. Benzocoumarin backbone is a multifunctional and affordable scaffold with a vast scope of biological activities. Journal of Medicinal and Chemical Sciences 2022;5(5):703–21.
  11. Mustafa YF, Abdulaziz NT. Biological potentials of hymecromone-based derivatives: A systematic review. Systematic Reviews in Pharmacy 2020;11(11):438–52.
  12. Mustafa YF. Synthesis, characterization and antibacterial activity of novel heterocycle, coumacine, and two of its derivatives. Saudi pharmaceutical journal 2018;26(6):870–5.
  13. Li M. Thionyl chloride - A versatile reagent. Synlett 2007;(16):2605–6.
  14. Mustafa YF, Oglah MK, Bashir MK. Conjugation of sinapic acid analogues with 5- Fluorouracil: Synthesis, preliminary cytotoxicity, and release study. Systematic Reviews in Pharmacy 2020;11(3):482–9.
  15. Mustafa YF. Chemotherapeutic applications of folate prodrugs: A review. NeuroQuantology 2021;19(8):99–112.
  16. Greenberg JA, Sammakia T. The Conversion of tert-Butyl Esters to Acid Chlorides Using Thionyl Chloride. Journal of Organic Chemistry 2017;82(6):3245–51.
  17. Mustafa YF. Synthesis, characterization and preliminary cytotoxic study of sinapic acid and its analogues. Journal of Global Pharma Technology 2019;11(9):1–10.
  18. Jumintono J, Alkubaisy S, Yánez Silva D, Singh K, Turki Jalil A, Mutia Syarifah S, et al. Effect of cystamine on sperm and antioxidant parameters of ram semen stored at 4 °C for 50 hours. Archives of Razi Institute 2021;76(4):981–9.
  19. Xu Z, Li K, Wang R, Duan X, Liu Q, Zhang R, et al. Electrochemical Effects of Lithium-Thionyl Chloride Battery by Central Metal Ions of Phthalocyanines-Tetraacetamide Complexes. Journal of The Electrochemical Society 2017;164(14):A3628–32.
  20. Mustafa YF. Classical approaches and their creative advances in the synthesis of coumarins: A brief review. Journal of Medicinal and Chemical Sciences 2021;4(6):612–25.
  21. Atia YA, Bokov DO, Zinnatullovich KR, Kadhim MM, Suksatan W, Abdelbasset WK, et al. The role of amino acid functionalization for improvement of adsorption Thioguanine anticancer drugs on the boron nitride nanotubes for drug delivery. Materials Chemistry and Physics 2022;278(October 2021):125664.
  22. Do Amaral DN. Thionyl chloride (CAS No 7719-09-7). Revista Virtual de Quimica 2013;5(6):1204–8.
  23. Mustafa YF, Oglah MK, Bashir MK, Mohammed ET, Khalil RR. Mutual prodrug of 5-ethynyluracil and 5-fluorouracil : Synthesis and pharmacokinetic profile. Clinical Schizophrenia and Related Psychoses 2021;15(5):1–6.
  24. Abdelbasset WK, Jasim SA, Sharma SK, Margiana R, Bokov DO, Obaid MA, et al. Alginate-Based Hydrogels and Tubes, as Biological Macromolecule-Based Platforms for Peripheral Nerve Tissue Engineering: A Review. Annals of Biomedical Engineering 2022;50(6):628–53.
  25. Chaudhari SS, Akamanchi KG. Thionyl chloride-benzotriazole in methylene chloride: A convenient solution for conversion of alcohols and carboxylic acids expeditiously into alkyl chlorides and acid chlorides by simple titration. Synlett 1999;(11):1763–5.
  26. Mustafa YF. Synthesis, characterization, and biomedical assessment of novel bisimidazole-coumarin conjugates. Applied Nanoscience 2023;13:1907–18.
  27. Jebir RM, Mustafa YF. Watermelon Allsweet: A promising natural source of bioactive products. Journal of Medicinal and Chemical Sciences 2022;5(5):652–66.
  28. Jasim SF, Mustafa YF. Synthesis and Antidiabetic Assessment of New Coumarin-Disubstituted Benzene Conjugates: An In Silico-In Virto Study. Journal of Medicinal and Chemical Sciences 2022;5(6):887–99.
  29. Tapasi Kalita PBM. One-Pot Synthesis of Amide, Dipeptide, Ester and Hydroxamate Using Oxyma and Thionyl Chloride (SOCl2). chemistry europe 2021;6(44):12281–7.
  30. Oglah MK, Mustafa YF. Synthesis, antioxidant, and preliminary antitumor activities of new curcumin analogues. Journal of Global Pharma Technology 2020;12(2):854–62.
  31. Budi HS, Jameel MF, Widjaja G, Alasady MS, Mahmudiono T, Mustafa YF, et al. Study on the role of nano antibacterial materials in orthodontics (a review). Brazilian Journal of Biology 2024;84(e257070):1–7.
  32. Ram RN, Meher NK. A simple method for the preparation of monomethyl esters of dicarboxylic acids by selective esterification of the nonconjugated carboxyl group in the presence of an aromatic or conjugated carboxyl group. Journal of Chemical Research - Part S 2000;75(6):282–3.
  33. Kasim SM, Abdulaziz NT, Mustafa YF. Synthesis and biomedical activities of coumarins derived from natural phenolic acids. Journal of Medicinal and Chemical Sciences 2022;5(4):546–60.
  34. Hsieh HK, Tsao LT, Wang JP, Lin CN. Synthesis and Anti-inflammatory Effect of Chalcones. Journal of Pharmacy and Pharmacology 2010;52(2):163–71.
  35. Lin YM, Zhou Y, Flavin MT, Zhou LM, Nie W, Chen FC. Chalcones and flavonoids as anti-tuberculosis agents. Bioorganic and Medicinal Chemistry 2002;10(8):2795–802.
  36. Salehi B, Quispe C, Chamkhi I, El Omari N, Balahbib A, Sharifi-Rad J, et al. Pharmacological Properties of Chalcones: A Review of Preclinical Including Molecular Mechanisms and Clinical Evidence. Frontiers in Pharmacology 2021;11(January).
  37. Khalil RR, Mohammed ET, Mustafa YF. Various promising biological effects of Cranberry extract: A review. Clinical Schizophrenia and Related Psychoses 2021;15(S6):1–9.
  38. Jasim SF, Mustafa YF. Synthesis, ADME Study, and antimicrobial evaluation of novel naphthalene-based derivatives. Journal of Medicinal and Chemical Sciences 2022;5(5):793–807.
  39. Mayer SG, Bard RR, Cantrell K. A safe and efficient technique for the production of HCl/DCl gas. Journal of Chemical Education 2008;85(6):847–8.
  40. Mahmood AAJ, Mustafa YF, Abdulstaar M. New coumarinic azo-derivatives of metoclopramide and diphenhydramine: Synthesis and in vitro testing for cholinesterase inhibitory effect and protection ability against chlorpyrifos. International Medical Journal Malaysia 2014;13(1):3–12.
  41. Zirak M, Eftekhari-Sis B. Kojic acid in organic synthesis. Turkish Journal of Chemistry 2015;39(3):439–96.
  42. Davies TQ, Willis MC. Rediscovering Sulfinylamines as Reagents for Organic Synthesis. Chemistry - A European Journal 2021;27(35):8918–27.
  43. Mustafa YF, Kasim SM, Al-Dabbagh BM, Al-Shakarchi W. Synthesis, characterization and biological evaluation of new azo-coumarinic derivatives. Applied Nanoscience (Switzerland) 2023;13:1095–1102.
  44. Jasim SF, Mustafa YF. A Review of Classical and Advanced Methodologies for Benzocoumarin Synthesis. Journal of Medicinal and Chemical Sciences 2022;5(5):676–94.
  45. Neugebauer FA, Fischer H, Crockett R, Krieger and C. 2,5-Dihydro-1,2,3,5-thiatriazole1-oxides, 2H-1,2,3,5-thiatriazol-1-ium salts, and 2,5-dihydro-1,2,3,5-thiatriazol-5-yl radicals. X-Ray molecular structure of 2,5-dihydro-2,4-diphenyl-1,2,3,5-thiatriazole 1-oxide and 2,4-diphenyl-2H-1,2,3,5-thiatriazol-1-i. J Chem Soc, Perkin Trans 2, 1990;(9):1619–26.
  46. Rohmah MK, Salahdin OD, Gupta R, Muzammil K, Qasim MT, Al-qaim ZH, et al. Modulatory role of dietary curcumin and resveratrol on growth performance, serum immunity responses, mucus enzymes activity, antioxidant capacity and serum and mucus biochemicals in the common carp, Cyprinus carpio exposed to abamectin. Fish and Shellfish Immunology 2022;129(June):221–30.
  47. Ghosh M. New polymer synthesis: Polymers possessing diiminosulfoxide functionality in the backbone. Journal of Macromolecular Science: Part A - Chemistry 1990;27(2):137–47.
  48. Khalil RR, Mohammed ET, Mustafa YF. Evaluation of in vitro antioxidant and antidiabetic properties of Cydonia Oblonga seeds’ extracts. Journal of Medicinal and Chemical Sciences 2022;5(6):1048–58.
  49. Ismael RN, Mustafa YF, Al-Qazaz HK. Citrullus lanatus, a Potential Source of Medicinal Products: A Review. Vol. 5, Journal of Medicinal and Chemical Sciences. 2022. p. 607–18.
  50. Zheng J, Tan F, Hartman R. Simple Spectrophotometry Method for the Determination of Sulfur Dioxide in an Alcohol-Thionyl Chloride Reaction. Analytica Chimica Acta 2015;
  51. Mohammed ET, Khalil RR, Mustafa YF. Phytochemical Analysis and Antimicrobial Evaluation of Quince Seeds’ Extracts. Journal of Medicinal and Chemical Sciences 2022;5(6):968–79.
  52. Abdulaziz NT, Al-bazzaz FY, Mustafa YF. Natural products for attenuating Alzheimer’s disease: A narrative review. Eurasian Chemical Communications 2023;5(4):358–70.
  53. Tanaka S, Sugihara Y, Sakamoto A, Ishii A, Nakayama J. The Thiosulfinyl Group Serves as a Stereogenic Center and Shows Diamagnetic Anisotropy Similar to That of the Sulfinyl Group. Journal of the American Chemical Society 2003;125(30):9024–5.
  54. Setia Budi H, Mustafa YF, Al-Hamdani MM, Surendar A, Ramezani M. Synthesis of heterocycles from propargylamines. Synthetic Communications 2021;51(24):3694–716.
  55. Yuzuru U, Seizi K. Reaction of N-Aroyl-N-t-butylhydroxylamines with Thionyl Chloride. Synthesis of Substituted Benzohydroximoyl Chlorides. Bulletin of the Chemical Society of Japan 1984;57(7):2011–2.
  56. Jebir RM, Mustafa YF. Novel coumarins isolated from the seeds of Citrullus lanatus as potential antimicrobial agents. Eurasian Chemical Communications 2022;4(8):692–708.
  57. Abdulaziz NT, Mustafa YF. Antibacterial and Antitumor Potentials of Some Novel Coumarins. International Journal of Drug Delivery Technology 2022;12(1):239–47.
  58. Waheed SA, Mustafa YF. Synthesis and evaluation of new coumarins as antitumor and antioxidant applicants. Journal of Medicinal and Chemical Sciences 2022;5(5):808–19.
  59. Han Y, Cai L. An efficient and convenient synthesis of formamidines. Tetrahedron Letters 1997;38(31):5423–6.
  60. Al-hatim RR, Al-alnabi DIB, Al-younis ZK, Al-shawi SG, Singh K, Abdelbasset WK, et al. Extraction of tea polyphenols based on orthogonal test method and its application in food preservation. Food Science and Technology 2022;42:e70321.
  61. Hudabaierdi R, Wusiman A, Mulati A. Improved Synthesis of N-Sulfonylformamidine Derivatives Promoted by Thionyl Chloride. Phosphorus, Sulfur, and Silicon and the Related Elements 2017;192(5):485–9.
  62. Mustafa YF, Zain Al-Abdeen SH, Khalil RR, Mohammed ET. Novel functionalized phenyl acetate derivatives of benzo [e]-bispyrone fused hybrids: Synthesis and biological activities. Results in Chemistry 2023;5:100942.
  63. Wusiman A, Hudabaierdi R. Efficient synthesis of N-oxysulfonyl formamidines through thionyl chloride-promoted reaction of sulfamates with formamides. Synthetic Communications 2017;47(21):2015–21.
  64. Jebir RM, Mustafa YF. Natural Products Catalog of Allsweet Watermelon Seeds and Evaluation of Their Novel Coumarins as Antimicrobial Candidates. Journal of Medicinal and Chemical Sciences 2022;5(5):831–47.
  65. Hammershøi A, Hartshorn RM, Sargeson AM. Oxidation of Chelated Amino Acids to Imine Derivatives with Thionyl Chloride. Inorganic Chemistry 1990;29(22):4525–30.
  66. Mustafa YF. Modern Developments in the Application and Function of Metal/Metal Oxide Nanocomposite–Based Antibacterial Agents. BioNanoScience 2023;13:840–52.
  67. Beattie JF, Hales NJ. Unusual oxidation in thionyl chloride: novel synthesis of methyl 3-alkoxy-1,4-dioxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylates. J Chem Soc, Perkin Trans 1, 1992;(7):751–2.
  68. Patra I, Ansari MJ, Saadoon N, Mashhadani ZI Al, Obaid NH, Alawsi T, et al. Insights into the Electronic Properties of Coumarins : A Comparative Study Photocatalytic Degradation of Methylene Blue. Physical Chemistry Research 2023;11(2):437–47.
  69. Feng S, Panetta CA GD. An unusual oxidation of a benzylic methylene group by thionyl chloride: a synthesis of 1, 3-dihydro-2-[2-(dimethyl-amino)ethyl]-1, 3-dioxopyrrolo[3, 4-c]acridine derivatives. J Org Chem 2001;66(2):606–12.
  70. Hammoodi SH, Ismael SS, Mustafa YF. Mutual prodrugs for colon targeting: A review. Eurasian Chemical Communications 2022;4(12):1251–65.
  71. Terrasson V, Planas JG, Prim D, Viñas C, Teixidor F, Light ME, et al. Cooperative effect of carborane and pyridine in the reaction of carboranyl alcohols with thionyl chloride: Halogenation versus oxidation. Journal of Organic Chemistry 2008;73(22):9140–3.
  72. Jasim SF, Mustafa YF. New fused-coumarin composites: Synthesis, anticancer and antioxidant potentials evaluation. Eurasian Chemical Communications 2022;4(7):607–19.
  73. Ahmed BA, Mustafa YF, Ibrahim BY. Isolation and characterization of furanocoumarins from Golden Delicious apple seeds. Journal of Medicinal and Chemical Sciences 2022;5(4):537–45.
  74. Abdulaziz NT, Mustafa YF. The Effect of Heat Variable on the Chemical Composition and Bioactivities of a Citrullus lanatus Seed Aqueous Extracts. Journal of Medicinal and Chemical Sciences 2022;5(7):1166–76.
  75. Deboprosad M, Lia SY, Belluccib L, Lainoc T, Tafid A, Guccionee S, et al. Stereoretentive Chlorination of Cyclic Alcohols Catalyzed by Titanium (IV) Tetrachloride: Evidence for a Front Side Attack Mechanism. J Org Chem 2013;78(5):2118–27.
  76. Waheed SA, Mustafa YF. The in vitro effects of new albocarbon-based coumarins on blood glucose-controlling enzymes. Journal of Medicinal and Chemical Sciences 2022;5(6):954–67.
  77. Leggio A, Belsito EL, Luca G De, Gioia ML Di, Leotta V, Romio E. One-pot synthesis of amides from carboxylic acids activated using thionyl chloride †. RSC Advances 2016;6:34468–75.
  78. Faria JV, Vegi PF, Miguita AGC, Santos MS dos, Silva M, Boechat N, et al. Recently reported biological activities of pyrazole compounds. Bioorganic & Medicinal Chemistry journal 2017;25(21):5891–903.
  79. Gudala S, Ambati SR, Patel JL, Vedula RR, Penta S. An Ef fi cient Synthesis of Pyrazolyl-1 , 2 , 3-thiadiazoles via Hurd – Mori Reaction. 2019;
  80. Al-Shakarchi W, Abdulaziz NT, Mustafa YF. A review of the chemical, pharmacokinetic, and pharmacological aspects of quercetin. Eurasian Chemical Communications 2022;4(7):645–56.
  81. Rodriguez D, Quint D, Garcia A, Sa C, Dom D. Intramolecular formal [ 4 + 2 ] cycloaddition reactions of secondary and tertiary aryldiacetylene alcohols. Tetrahedron Letters 2004;45:4711–4.
  82. Waheed SA, Mustafaa YF. Novel naphthalene-derived coumarin composites: synthesis, antibacterial, and antifungal activity assessments. Eurasian Chemical Communications 2022;4(8):709–24.
  83. Ismael RN, Mustafa YF, Al-Qazaz HK. Cancer-curative potential of novel coumarins from watermelon princess: A scenario of their isolation and activity. Eurasian Chemical Communications 2022;4(7):657–72.
  84. Abdelbasset WK, Elkholi SM, Ismail KA, AL-Ghamdi HS, Mironov S, Ridha HSH, et al. Mequinol-loaded carboxymethyl cellulose/chitosan electrospun wound dressing as a potential candidate to treat diabetic wounds. Cellulose 2022;29(14):7863–81.
  85. Cheng S, Li B, Yuan Z, Zhang F, Liu J. Development of a lifetime prediction model for lithium thionyl chloride batteries based on an accelerated degradation test. Microelectronics Reliability 2016;65:274–9.
  86. Al-shakarchi W, Saber Y, Merkhan MM, Mustafa YF. Sub Chronic Toxicity Study of Coumacines. Pharmacognosy Journal 2023;15(1):160–4.
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