Tetramethylenedisulfotetramine

Base Information

• Chemical Name: Tetramethylenedisulfotetramine
• CAS No.: 80-12-6
• Deprecated CAS: 7076-28-0
• Molecular Formula: C4H8 N4 O4 S2
• Molecular Weight: 240.28
• European Community (EC) Number: 804-552-0
• NSC Number: 172824
• UNII: F6TS3WME05
• DSSTox Substance ID: DTXSID8040307
• Nikkaji Number: J21.381K
• Wikipedia: Tetramethylenedisulfotetramine
• Wikidata: Q7706590
• NCI Thesaurus Code: C163710
• Mol file: 80-12-6.mol

Synonyms:disulfotetraazaadamantane;DSTA;tetramethylenedisulfotetramine;tetramethylenedisulphotetramine;tetramine

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Chemical Property of Tetramethylenedisulfotetramine

Chemical Property:

• Vapor Pressure: 1.43E-09mmHg at 25°C
• Melting Point: 242.5°C (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 498.1°C at 760 mmHg
• PKA: -11.52±0.20(Predicted)
• Flash Point: 255.1°C
• PSA: 207.58000
• Density: 2.28g/cm³
• LogP: 1.74080
• Storage Temp.: ?20°C
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 239.99869710
• Heavy Atom Count: 14
• Complexity: 379

Purity/Quality:

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1N2CN3CN(S2(=O)=O)CN1S3(=O)=O
• Description: Tetramethylenedisulfotetramine (2,6-dithia-1,3,5,7-tetraazadamantane, 2,2,6,6-tetraoxide, TETS) is a highly toxic heteroadamantane rodenticide. It is an odorless, tasteless, white crystalline powder that is slightly soluble in water (0.25 mg ml-1), dimethyl sulfoxide and acetone. It was originally synthesized in 1933 as a resinous condensation product of sulfamide and formaldehyde and used commercially in pillows and upholstery as an impregnating stiffening and antimold agent. However, in 1950, a massive poisoning of German workers in the furniture manufacturing industry was linked to ‘Crinex’ wool, which contained TETS as a byproduct of processing. Early experimental studies in rodents revealed that TETS was an extremely toxic convulsant agent. It was also discovered at this time that TETS is a highly effective rodent repellent, which resulted in its use during reforestation projects to prevent seed predation by rodents. However, because of its high toxicity in mammals, including humans, and its persistence in the environment, many countries banned its production and use in 1984. This ban became worldwide when China issued similar restrictions in 1991. However, due to its relative ease of synthesis and low cost, TETS remains available on the black market, particularly in many rural areas of China and in regions outside of China that have large Asian populations.
• Uses: Despite the worldwide ban on its production and use, TETS continues to be used illicitly as a rodenticide in various regions of the world. In China, TETS is known as ‘Dushuqiang’, ‘Meishuming,’ or ‘Shanbudao.’ In 2000, the National Poison Control Center of China revealed that 74% of commercial rodenticides contained illegal chemicals, with TETS found in nearly 50% of these pesticides. From 1977 to 2002, it was estimated that there were thousands of cases of TETS poisoning in China, resulting in hundreds of deaths. A more recent analysis indicates that between 1991 and 2010, there were over 14 000 cases of TETS intoxication in China, of which 932 resulted in death. In 2003, the first case of TETS intoxication in the United States was reported: a healthy 15-month-old girl was poisoned following accidental ingestion of a rodenticide imported from China that contained TETS. While many cases are thought to be due to accidental poisonings, there have been numerous reports of TETS being used to intentionally poison humans.

Technology Process of Tetramethylenedisulfotetramine

There total 5 articles about Tetramethylenedisulfotetramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

Dimethoxymethane (109-87-5) → tetramethylenedisulfotetramine (80-12-6)

Guidance literature:

With SULFAMIDE; trifluoroacetic acid; for 6h; Ambient temperature;

DOI:10.1021/jo00312a013

Reference yield:

4,10-dithia-1,3,5,7,9,11-hexaaza-tetracyclo[5.5.1.13,11.15,9]pentadecane 4,4,10,10-tetraoxide (54475-62-6) → tetramethylenedisulfotetramine (80-12-6)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1002/jhet.5570110503

Reference yield:

Homopentamethylen-tetraminsulfon (37391-75-6) → tetramethylenedisulfotetramine (80-12-6)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1002/jhet.5570110503

upstream raw materials:

formaldehyd

4,10-dithia-1,3,5,7,9,11-hexaaza-tetracyclo[5.5.1.1^3,11.1^5,9]pentadecane 4,4,10,10-tetraoxide

Homopentamethylen-tetraminsulfon

1,3,5,7-Tetraaza-2-thia-adamantan-2-dioxyd,Pentamethylentetraminsulfon