4,4-Dichloro-1,3-dithietane-2-one
The title compound, 4,4-dichloro-1,3-dithietane-2-one, was encountered when opening a commercial capped amber bottle labeled “thiophosgene” that had been stored in a cold room (4 °C) for decades without any special precautions. Treating it as an unknown, the structure was established by single cryst...
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| Format: | Article |
| Language: | English |
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MDPI AG
2025-06-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2025/2/M2021 |
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| _version_ | 1850167695633285120 |
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| author | Tracy R. Thompson William W. Brennessel Erik S. Goebel Matthew J. Turcotte George Barany |
| author_facet | Tracy R. Thompson William W. Brennessel Erik S. Goebel Matthew J. Turcotte George Barany |
| author_sort | Tracy R. Thompson |
| collection | DOAJ |
| description | The title compound, 4,4-dichloro-1,3-dithietane-2-one, was encountered when opening a commercial capped amber bottle labeled “thiophosgene” that had been stored in a cold room (4 °C) for decades without any special precautions. Treating it as an unknown, the structure was established by single crystal X-ray analysis, and confirmed by <sup>13</sup>C NMR, FTIR, melting behavior, and elemental analysis; its behavior under several mass spectrometric conditions was also examined. The dithietane appears to be a spontaneously formed cyclodimer of thiophosgene in which exactly one (not zero, not both) of the dichloromethylene moieties has been hydrolyzed to a carbonyl function. The relative long-term stability of the hydrolyzed dimer, along with a pathway back to thiophosgene, suggests that it might serve as a storage vehicle for toxic thiophosgene. Furthermore, as noted elsewhere, the title compound reacts with nucleophiles under mild aqueous conditions, suggesting that it may be a useful probe in chemical biology. |
| format | Article |
| id | doaj-art-40f19d9ecc234eee882b52cbe0f490cb |
| institution | OA Journals |
| issn | 1422-8599 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj-art-40f19d9ecc234eee882b52cbe0f490cb2025-08-20T02:21:08ZengMDPI AGMolbank1422-85992025-06-0120252M202110.3390/M20214,4-Dichloro-1,3-dithietane-2-oneTracy R. Thompson0William W. Brennessel1Erik S. Goebel2Matthew J. Turcotte3George Barany4Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USADepartment of Chemistry, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, University of Minnesota, Minneapolis, MN 55455, USADepartment of Chemistry, University of Minnesota, Minneapolis, MN 55455, USADepartment of Chemistry, University of Minnesota, Minneapolis, MN 55455, USAThe title compound, 4,4-dichloro-1,3-dithietane-2-one, was encountered when opening a commercial capped amber bottle labeled “thiophosgene” that had been stored in a cold room (4 °C) for decades without any special precautions. Treating it as an unknown, the structure was established by single crystal X-ray analysis, and confirmed by <sup>13</sup>C NMR, FTIR, melting behavior, and elemental analysis; its behavior under several mass spectrometric conditions was also examined. The dithietane appears to be a spontaneously formed cyclodimer of thiophosgene in which exactly one (not zero, not both) of the dichloromethylene moieties has been hydrolyzed to a carbonyl function. The relative long-term stability of the hydrolyzed dimer, along with a pathway back to thiophosgene, suggests that it might serve as a storage vehicle for toxic thiophosgene. Furthermore, as noted elsewhere, the title compound reacts with nucleophiles under mild aqueous conditions, suggesting that it may be a useful probe in chemical biology.https://www.mdpi.com/1422-8599/2025/2/M20214,4-dichloro-1,3-dithietane-2-onethiophosgenelong-term storage of thiophosgenethiophosgene dimerpartially hydrolyzed thiophosgene dimerX-ray structural analysis |
| spellingShingle | Tracy R. Thompson William W. Brennessel Erik S. Goebel Matthew J. Turcotte George Barany 4,4-Dichloro-1,3-dithietane-2-one Molbank 4,4-dichloro-1,3-dithietane-2-one thiophosgene long-term storage of thiophosgene thiophosgene dimer partially hydrolyzed thiophosgene dimer X-ray structural analysis |
| title | 4,4-Dichloro-1,3-dithietane-2-one |
| title_full | 4,4-Dichloro-1,3-dithietane-2-one |
| title_fullStr | 4,4-Dichloro-1,3-dithietane-2-one |
| title_full_unstemmed | 4,4-Dichloro-1,3-dithietane-2-one |
| title_short | 4,4-Dichloro-1,3-dithietane-2-one |
| title_sort | 4 4 dichloro 1 3 dithietane 2 one |
| topic | 4,4-dichloro-1,3-dithietane-2-one thiophosgene long-term storage of thiophosgene thiophosgene dimer partially hydrolyzed thiophosgene dimer X-ray structural analysis |
| url | https://www.mdpi.com/1422-8599/2025/2/M2021 |
| work_keys_str_mv | AT tracyrthompson 44dichloro13dithietane2one AT williamwbrennessel 44dichloro13dithietane2one AT eriksgoebel 44dichloro13dithietane2one AT matthewjturcotte 44dichloro13dithietane2one AT georgebarany 44dichloro13dithietane2one |