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1,3,5-trithiane

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Origin: China

Cas No: 291-21-4

Specification: 99%min

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  • Products Specification
  • Product Description

  • Property

    CAS No.: 291-21-4 Formula: C3H6S3 Molecular Weight: 138.27500

    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. It is the trimer of thioformaldehyde.
    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

    Basic Info

    Chemical Name 1,3,5-trithiane
    Synonyms

    Trithiometaformaldehyde;
    1,3,5-trithian;
    sym-Trithian;
    1,3,5-Trithiane;
    [1,3,5]trithiane;
    Thioform [Czech];
    Thioformaldehyde trimer;
    s-Trithiane;
    Trithioformaldehyde;
    Thioform;
    sym-Trithiane;
    1,3,5-trithiacyclohexane;
    Trimethylene trisulfide;

    CAS No. 291-21-4
    Molecular Formula C3H6S3
    Molecular Weight 138.27500
    PSA 75.90000
    LogP 2.07210

    Properties

    Appearance & Physical State white to off-white crystalline powder
    Density 1.318g/cm3
    Boiling Point 230.7ºC at 760mmHg
    Melting Point 215-220ºC
    Refractive Index 1.651
    Vapor Pressure 0.0983mmHg at 25°C

    Safety Info

    RTECS YL8225000
    Safety Statements S22-S24/25
    HS Code 2934999090
    WGK Germany 3

    Synthesis Route

    [1,3,5]trithiane-1-oxide→1,3,5-trithiane
    Formaldehyde→1,3,5-trithiane
    carbon disulfide→1,3,5-trithiane

    GC Analysis

    Column type Active phase Temperature (°C) Retention Index (I) Temperature Control Method
    Capillary BPX-5 - 1271. temperature ramp
    Capillary OV-1 - 1259. temperature ramp
    Capillary SPB-1 - 1271. temperature ramp

    Toxicity

    Exposure Route Type of Test Species Observed Dose/Duration Toxic Effects
    Administration onto the skin Standard Draize test Rodent - rabbit 500 mg/24H -
    Administration into the eye Standard Draize test Rodent - rabbit 500 mg/24H -

    Precursor

    Formaldehyde
    morpholin-4-ylmethanethiol
    [1,3,5]trithiane-1-oxide
    piperidino-methanethiol

    Downstream Product

    chloro-(chloromethyldisulfanyl)methane
    chloro(chloromethylsulfanyl)methane
    tetrachloromethane
    Benzyl Chloromethyl Sulfide

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