cyhexatin
{{Short description|Organotin compound}}
{{Chembox
| Name = Cyhexatin
| IUPACName = Tricyclohexyltin hydroxide
| OtherNames = {{ubl|Cyhexatin|Lintex{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Cyhexatin | title=Cyhexatin }}|Plictran|TCTH|Tricyclohexylhydroxytin|Tricyclohexyltin(IV) hydroxide|Tricyclohexylhydroxylstannane|Tricyclohexylstannanol}}
| ImageFile = Cyhexatin.svg
| ImageSize =
| ImageAlt = Cyhexatin
| ImageCaption =
| ImageName =
| Section1 = {{Chembox Identifiers
| CASNo = 13121-70-5
| Beilstein = 6099492
| ChEBI = 4036
| ChemSpiderID = 10801387
| ChemSpiderID_Comment =
| KEGG = C11093
| Gmelin = 31094
| PubChem = 6327054
| PubChem_Comment = (incorrect structure)
| Jmol =
| RTECS = WH8750000
| UNNumber = 2811
| UNII = 8YJV11QB4R
| EINECS = 236-049-1
| StdInChI=1S/3C6H11.H2O.Sn/c3*1-2-4-6-5-3-1;;/h3*1H,2-6H2;1H2;/q;;;;+1/p-1
| StdInChIKey = WCMMILVIRZAPLE-UHFFFAOYSA-M
| SMILES = C1CCC(CC1)[Sn](C2CCCCC2)(C3CCCCC3)O
}}
| Section2 = {{Chembox Properties
| Properties_ref =
| Formula = {{chem2|(C6H11)3SnOH}}
| C=18|H=34|O=1|Sn=1
| Appearance = Colorless crystals or white crystalline powder
| MeltingPtC = 196
| MeltingPt_notes = Decomposes above {{cvt|121 to 131|C|F K}}
| BoilingPtC = 228
| BoilingPt_notes = (decomposes)
| Solubility = Almost insoluble (less than 1 mg/L)
| SolubleOther = {{ubl|Acetone 1.3 g/L|Dichloromethane 34 g/L|Carbon tetrachloride 28 g/L|Xylenes 3.6 g/L}}
| Solvent1 = Chloroform
| Solvent2 = Methanol
| Solvent3 = Toluene
| Solvent4 = Benzene
}}
| Section3 =
| Section4 = {{Chembox Thermochemistry
| Thermochemistry_ref =
| HeatCapacity =
| Entropy =
| DeltaHform =
| DeltaGfree =
| DeltaHcombust =
| DeltaHfus =
| DeltaHvap =
| DeltaHsublim =
| HHV =
| LHV =
}}
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards
| Hazards_ref =
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|H302|H312|H332|H410}}
| PPhrases = {{P-phrases|P261|P264|P270|P271|P273|P280|P301+P317|P302+P352|P304+P340|P317|P321|P330|P362+P364|P391|P501}}
| MainHazards = Kidneys and liver damage. High exposure damages the nervous system.https://nj.gov/health/eoh/rtkweb/documents/fs/0590.pdf
| IngestionHazard = Abdominal pain, diarrhea, nausea, vomiting
| InhalationHazard = Respiratory system and throat irritation
| EyeHazard = Irritation and burns
| SkinHazard = Irritation and burns, can be absorbed into the body through the skin
| NFPA-H =
| NFPA-F =
| NFPA-I =
| NFPA-S =
| NFPA_ref =
| FlashPt =
| FlashPtC =
| FlashPt_notes =
| FlashPt_ref =
| AutoignitionPt =
| AutoignitionPtC =
| AutoignitionPt_ref=
| AutoignitionPt_notes=
| ExploLimits =
| TLV =
| TLV-TWA =
| TLV-STEL =
| TLV-C =
| LD50 = {{ubl|458 mg/kg (oral, rabbit)|2422 mg/kg (skin, rabbit)|180 mg/kg (oral, rat)|446 mg/kg (skin, rat)|275 mg/kg (oral, mouse)|800 mg/kg (cat, oral)|800 mg/kg (oral, dog)|800 mg/kg (oral, monkey)|780 mg/kg (oral, guinea pig)|654 mg/kg (oral, chicken)|255 mg/kg (oral, quail)}}
| LDLo =
| LC50 = 244 mg/m3 (inhalation, rat), 290 mg/m3 (inhalation, mouse)
| LCLo =
| PEL =
| REL =
| IDLH =
| NIOSH_id =
| NIOSH_ref =
| ExternalSDS =
}}
| Section8 = {{Chembox Related
| Related_ref =
| OtherAnions =
| OtherCations =
| OtherFunction =
| OtherFunction_label =
| OtherCompounds =
}}
| Section9 =
}}
Cyhexatin, also known as tricyclohexyltin hydroxide is an organometallic compound of tin with the chemical formula {{chem2|(C6H11)3SnOH}}.
Properties
Reactions
Cyhexatin is stable in aqueous suspensions in neutral and alkaline conditions (pH above 6), but reacts exothermically with strong acids, acting as a base, to form salts.{{which|date=January 2023}} Reacts with strong oxidizers. Decomposes upon exposure to ultraviolet light to dicyclohexyltin oxide {{chem2|(C6H11)2SnO}} (which is not an analog of ketones {{chem2|R2C\dO}} because it exists as a polymer) and cyclohexylstannanoic acid {{chem2|(C6H11)SnO2H}}. Contact with metals may emit flammable hydrogen gas. Upon heating above {{cvt|120|C|F}} it decomposes to bis(tricyclohexyltin) oxide {{chem2|((C6H11)3Sn)2O}}, emitting irritating and toxic fumes and acrid smoke.
:{{chem2|2 (C6H11)3SnOH → ((C6H11)3Sn)2O + H2O}}
Uses
In agriculture, cyhexatin is used as a pesticide against insects, as well as parasitic mites that attack plants, like vegetables (e.g. cucurbits), fruit trees (e.g. pome fruits, stone fruits), hops, walnut, strawberry, vines and ornamentals. It acts by inhibiting mitochondrial ATP synthase, and is in IRAC group 12B). The chemical is not used in the United States.{{cite web |title=Registration Review; Pesticide Dockets Opened for Review and Comment |url=https://www.regulations.gov/document/EPA-HQ-OPP-2009-0870-0001 |publisher=US EPA |access-date=28 April 2023 |date=December 16, 2009}}
Hazards and toxicity
Cyhexatin is not combustible, but decomposes upon heating to produce corrosive and toxic fumes. Some components of those fumes are oxidizers, thus, they can cause combustible materials to ignite, like wood, oil, some plastics, paper and clothes. Containers of cyhexatin may explode when heated. Cyhexatin is very toxic to aquatic life.
Cyhexatin is not classified as a human carcinogen, but is classified as a teratogen. It is toxic by contact with skin, inhalation and ingestion. The compound and its fumes irritate and burn eyes. Contact with skin causes pruritus and burns. Cyhexatin can be absorbed into the body through the skin, and skin should be washed immediately upon contact with this chemical. Inhalation of its fumes causes irritation of the respiratory system, coughing, headache, dizziness and sore throat. It can cause abdominal pain, diarrhea, nausea and vomiting. It causes damage to kidneys and liver, as well as nervous system. Cyhexatin is a central nervous system depressant.