page_title: 1,3,5-Trithiane
hierarchical_section_title: 1,3,5-Trithiane
caption_attribution_description: English: sample of sym-trithiane
context_page_description: 1,3,5-Trithiane is the chemical compound with the formula (CH₂S)₃. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.
  Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde. In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.
  (CH₂S)₃ + RLi → (CH₂S)₂ + RH
  (CH₂S)₂ + R’Br → (CH₂S)₂ + LiBr
  (CH₂S)₂ + H₂O → R’CHO + ….
  Trithiane is the dithioacetal of formaldehyde. Other dithioacetals undergo similar reactions to the above.
  It is also a precursor to other organosulfur reagents. For example, chlorination in the presence of water affords the chloromethyl sulfonyl chloride:
  (CH₂S)₃ + 9 Cl₂ + 6 H₂O → 3 ClCH₂SO₂Cl + 12 HCl
context_section_description: 1,3,5-Trithiane is the chemical compound with the formula (CH₂S)₃.  This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups.  It is prepared by treatment of formaldehyde with hydrogen sulfide.
  Trithiane is a building block molecule in organic synthesis, being a masked source of formaldehyde.  In one application, it is deprotonated with organolithium reagents to give the lithium derivative, which can be alkylated.
  (CH₂S)₃  +  RLi  →   (CH₂S)₂(CHLiS)  +  RH
  (CH₂S)₂(CHLiS)  +  R’Br   →  (CH₂S)₂(CHR’S)  +  LiBr
  (CH₂S)₂(CHR’S)  +  H₂O   →  R’CHO  +  ….
  Trithiane is the dithioacetal of formaldehyde.  Other dithioacetals undergo similar reactions to the above.
  It is also a precursor to other organosulfur reagents.  For example, chlorination in the presence of water affords the chloromethyl sulfonyl chloride:
  (CH₂S)₃  +  9 Cl₂  +  6 H₂O   →   3 ClCH₂SO₂Cl  +  12 HCl
caption: Sample of sym-trithiane.
exif: {"Image Make": "Apple", "Image Model": "iPhone 6", "Image Orientation": "Horizontal (normal)", "Image XResolution": "72", "Image YResolution": "72", "Image ResolutionUnit": "Pixels/Inch", "Image Software": "11.4", "Image DateTime": "2018:07:13 11:19:27", "Image ExifOffset": "192", "GPS GPSLatitudeRef": "N", "GPS GPSLatitude": "[40, 6, 2151/100]", "GPS GPSLongitudeRef": "W", "GPS GPSLongitude": "[88, 13, 2467/100]", "GPS GPSAltitudeRef": "0", "GPS GPSAltitude": "27527/122", "GPS GPSTimeStamp": "[16, 19, 21]", "GPS GPSSpeedRef": "K", "GPS GPSSpeed": "0", "GPS GPSImgDirectionRef": "T", "GPS GPSImgDirection": "42617/173", "GPS GPSDestBearingRef": "T", "GPS GPSDestBearing": "42617/173", "GPS GPSDate": "2018:07:13", "GPS Tag 0x001F": "2691", "Image GPSInfo": "1620", "EXIF ExposureTime": "1/120", "EXIF FNumber": "11/5", "EXIF ExposureProgram": "Program Normal", "EXIF ISOSpeedRatings": "50", "EXIF ExifVersion": "0221", "EXIF DateTimeOriginal": "2018:07:13 11:19:27", "EXIF DateTimeDigitized": "2018:07:13 11:19:27", "EXIF ComponentsConfiguration": "YCbCr", "EXIF ShutterSpeedValue": "2653/384", "EXIF ApertureValue": "7892/3469", "EXIF BrightnessValue": "3241/547", "EXIF ExposureBiasValue": "0", "EXIF MeteringMode": "Pattern", "EXIF Flash": "Flash did not fire, auto mode", "EXIF FocalLength": "83/20", "EXIF SubjectArea": "[1631, 1223, 1795, 1077]", "EXIF SubSecTimeOriginal": "663", "EXIF SubSecTimeDigitized": "663", "EXIF FlashPixVersion": "0100", "EXIF ColorSpace": "sRGB", "EXIF ExifImageWidth": "1684", "EXIF ExifImageLength": "1750", "EXIF SensingMethod": "One-chip color area", "EXIF SceneType": "Directly Photographed", "EXIF ExposureMode": "Auto Exposure", "EXIF WhiteBalance": "Auto", "EXIF FocalLengthIn35mmFilm": "29", "EXIF SceneCaptureType": "Standard", "EXIF LensSpecification": "[83/20, 83/20, 11/5, 11/5]", "EXIF LensMake": "Apple", "EXIF LensModel": "iPhone 6 back camera 4.15mm f/2.2"}