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Chemical Compound Review

SOCl2     thionyl dichloride

Synonyms: HSDB 859, ACMC-1BIJW, CCRIS 1280, AG-H-08482, CHEBI:29290, ...
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Disease relevance of thionyl dichloride

  • The targeted compounds 1 and 2 were prepared by addition of the propargyl Gringard to the 5 alpha,6 alpha-epoxy bisketal 6 or the 5 alpha,6 alpha-epoxy diacetate 7 followed by dehydration of the 6 beta-propargyl 5 alpha-hydroxy diones 10 and 11 using thionyl chloride [1].
  • Thionyl-chloride-induced lung injury and bronchiolitis obliterans [2].

High impact information on thionyl dichloride

  • Esterification of amino acids with thionyl chloride acidified butanols for their gas chromatographic analysis [3].
  • Poly(methyl methacrylate-acrylic acid) microspheres were prepared and the acid groups were activated by using either carbodiimide (CDI) or thionyl chloride (SOCl2). alpha-Amylase was covalently bound on these activated microspheres [4].
  • Reduction (NaBH4) of 9 yielded the alcohol 32 (94%) which was treated with thionyl chloride followed by copper (I) cyanide and sodium iodide in acetonitrile to give the tricyclic-N-methoxycarbonyl nitrile 35 whose relative configuration was obtained by X-ray analysis [5].
  • Cyclization of a number of hydrazones including the partially acetylated sugar hydrazones by thionyl chloride gave regioselectively the respective angular isomer 1-substituted phenanthro [9, 10-e] [1, 2, 4] triazino [3, 4- and not the linear isomer [6].
  • Cyclization of 4 by the action of PPA or thionyl chloride afforded the corresponding indolyl- (5) and thiadiazolyl-(6) derivatives [7].

Chemical compound and disease context of thionyl dichloride


Biological context of thionyl dichloride

  • In contrast, the 4-(2-pyridinyl) analogue 11f was prepared by thionyl chloride mediated cyclization of the 5-¿N-(1,1-dimethyl-2-hydroxyethyl)aminocarbonyl¿ moiety of 16 to the 5-[2-(4,5-dihydro-4,4-dimethyloxazolin-2-yl)] ring system (11f) [9].
  • Hydrolysis of 3 gave the corresponding acids 4 which on treatment with thionyl chloride followed by ammonia afforded the corresponding carboxamides 5 [10].

Associations of thionyl dichloride with other chemical compounds


Gene context of thionyl dichloride

  • Piperidides were obtained by converting the fatty acids first to acyl chlorides via interaction with thionyl chloride and then to piperidyl carboxylates by action with 3-(hydroxymethyl)-N-methylpiperidine [12].

Analytical, diagnostic and therapeutic context of thionyl dichloride


  1. 6 beta-Propynyl-substituted steroids: mechanism-based enzyme-activated irreversible inhibitors of aromatase. Akkani, A., Paterlini, G., Gleason, W.B., Ojala, W.H., Abul-Hajj, Y.J. J. Med. Chem. (1997) [Pubmed]
  2. Thionyl-chloride-induced lung injury and bronchiolitis obliterans. Konichezky, S., Schattner, A., Ezri, T., Bokenboim, P., Geva, D. Chest (1993) [Pubmed]
  3. Esterification of amino acids with thionyl chloride acidified butanols for their gas chromatographic analysis. Molnár-Perl, I., Pintér-Szakács, M., Fábián-Vonsik, V. J. Chromatogr. (1987) [Pubmed]
  4. Stability of alpha-amylase immobilized on poly(methyl methacrylate-acrylic acid) microspheres. Aksoy, S., Tumturk, H., Hasirci, N. J. Biotechnol. (1998) [Pubmed]
  5. Experiments towards the synthesis of the ergot alkaloids and related structures. Part 8. The total synthesis of 4-methyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinoline-2-carbonitrile hydrochloride hemihydrate, an immediate precursor of the despyrrole analogues of lysergic acid and its amides. Bowman, M.A., Bowman, R.E., Davies, R.V., Haran, G., Harris, P.J., Smith, H.J., Steele, R.W., Walker, N., Whiting, K. Journal of enzyme inhibition and medicinal chemistry. (2002) [Pubmed]
  6. Synthesis of acyclo C-nucleosides of phenanthro[9,10-e][1,2, 4]triazino[3,4-c]-[1,2,4]triazoles, and their precursors. Hamed, A., Abo-Amaym, E.R., el Ashry el-S, H. Nucleosides Nucleotides (1998) [Pubmed]
  7. Synthesis of 3,5-disubstituted pyridines as antimicrobial agents. Attia, A., Abo-Ghalia, M.H., Abd el-Salam, O.I. Die Pharmazie. (1995) [Pubmed]
  8. Steroids 49. Investigations on the dehydration of 17 alpha-ethynyl-17 beta-hydroxysteroids. Vincze, I., Lökös, M., Bakos, T., Dancsi, A., Mák, M. Steroids (1993) [Pubmed]
  9. Synthesis and smooth muscle calcium channel antagonist effects of alkyl 1,4-dihydro-2,6-dimethyl-4-(pyridinyl)-5-[2-(4,5-dihydro- 4,4-dimethyloxazolin-2-yl)]-3-pyridinecarboxylates. Anana, R.D., Knaus, E.E. Arch. Pharm. (Weinheim) (1996) [Pubmed]
  10. Synthesis of some substituted pyrazole-3-carboxylic acids with possible hypoglycemic and antimicrobial activity. Mokhtar, H., Soliman, R. Die Pharmazie. (1978) [Pubmed]
  11. Chromatographic isolation and identification of methylated derivatives obtained from modified fibrinogen. Osbahr, A.J. Biomaterials (1980) [Pubmed]
  12. Piperidine ester derivatives in mass spectrometric analysis of fatty acids from human serum phospholipids and cholesteryl esters. Marnela, K.M., Moilanen, T., Jutila, M. Biomed. Environ. Mass Spectrom. (1988) [Pubmed]
  13. An economic synthesis of 1,2,3,4-tetra-O-acetyl-5-thio-D-xylopyranose and its transformation into 4-substituted-phenyl 1,5-dithio-D- xylopyranosides possessing antithrombotic activity. Bozó, E., Boros, S., Kuszmann, J., Gács-Baitz, E., Párkányi, L. Carbohydr. Res. (1998) [Pubmed]
  14. Anti-IgG immobilized controlled-pore glass. Thionyl chloride-activated succinamidopropyl-glass as a covalent immobilization matrix. Stabel, T.J., Casale, E.S., Swaisgood, H.E., Horton, H.R. Appl. Biochem. Biotechnol. (1992) [Pubmed]
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