Cyhexatin

Cyhexatin
Names
	IUPAC name Tricyclohexyltin hydroxide
	Other names Cyhexatin; Lintex; Plictran; TCTH; Tricyclohexylhydroxytin; Tricyclohexyltin(IV) hydroxide; Tricyclohexylhydroxylstannane; Tricyclohexylstannanol;
Identifiers
CAS Number	13121-70-5;
Beilstein Reference	6099492
ChEBI	CHEBI:4036;
ChemSpider	10801387;
ECHA InfoCard	100.032.757
EC Number	236-049-1;
Gmelin Reference	31094
KEGG	C11093;
PubChem CID	6327054 (incorrect structure);
RTECS number	WH8750000;
UNII	8YJV11QB4R;
UN number	2811
CompTox Dashboard (EPA)	DTXSID1032357 ;
	InChI InChI=1S/3C6H11.H2O.Sn/c31-2-4-6-5-3-1;;/h31H,2-6H2;1H2;/q;;;;+1/p-1 Key: WCMMILVIRZAPLE-UHFFFAOYSA-M;
	SMILES C1CCC(CC1)[Sn](C2CCCCC2)(C3CCCCC3)O;
Properties
Chemical formula	(C6H11)3SnOH
Molar mass	385.179 g·mol−1
Appearance	Colorless crystals or white crystalline powder
Odor	Nearly odorless
Melting point	196 °C (385 °F; 469 K) Decomposes above 121 to 131 °C (250 to 268 °F; 394 to 404 K)
Boiling point	228 °C (442 °F; 501 K) (decomposes)
Solubility in water	Almost insoluble (less than 1 mg/L)
Solubility	Acetone 1.3 g/L; Dichloromethane 34 g/L; Carbon tetrachloride 28 g/L; Xylenes 3.6 g/L;
Solubility in Chloroform	216 g/kg
Solubility in Methanol	37 g/kg
Solubility in Toluene	10 g/kg
Solubility in Benzene	16 g/kg
Vapor pressure	Negligible
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Kidneys and liver damage. High exposure damages the nervous system.
Ingestion hazards	Abdominal pain, diarrhea, nausea, vomiting
Inhalation hazards	Respiratory system and throat irritation
Eye hazards	Irritation and burns
Skin hazards	Irritation and burns, can be absorbed into the body through the skin
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332, H410
Precautionary statements	P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, P501
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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);
LC50 (median concentration)	244 mg/m3 (inhalation, rat), 290 mg/m3 (inhalation, mouse)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyhexatin, also known as tricyclohexyltin hydroxide is an organometallic compound of tin with the chemical formula (C₆H₁₁)₃SnOH.

Properties

Cyhexatin forms colorless crystals or white crystalline powder. It is practically insoluble in water. The powder is wettable by water.^[1]

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?] Reacts with strong oxidizers. Decomposes upon exposure to ultraviolet light to dicyclohexyltin oxide (C₆H₁₁)₂SnO (which is not an analog of ketones R₂C=O because it exists as a polymer) and cyclohexylstannanoic acid (C₆H₁₁)SnO₂H. Contact with metals may emit flammable hydrogen gas. Upon heating above 120 °C (248 °F) it decomposes to bis(tricyclohexyltin) oxide ((C₆H₁₁)₃Sn)₂O, emitting irritating and toxic fumes and acrid smoke.^[1]

2 (C₆H₁₁)₃SnOH → ((C₆H₁₁)₃Sn)₂O + H₂O

Uses

Cyhexatin is used in paints.^[2]

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.^[1] It acts by inhibiting mitochondrial ATP synthase, and is in IRAC group 12B). The chemical is not used in the United States.^[4]

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.^[1]

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.^[1] It causes damage to kidneys and liver, as well as nervous system.^[2] Cyhexatin is a central nervous system depressant.^[1]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v ^w ^x "Cyhexatin".
^ ^a ^b ^c ^d https://nj.gov/health/eoh/rtkweb/documents/fs/0590.pdf
^ "Cyhexatin". pubchem.ncbi.nlm.nih.gov.
^ "Registration Review; Pesticide Dockets Opened for Review and Comment". US EPA. December 16, 2009. Retrieved 28 April 2023.

[pubchem-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s ^t ^u ^v ^w ^x "Cyhexatin".

[newjerseydepartment-2] ttps://nj.gov/health/eoh/rtkweb/documents/fs/0590.pdf

[3] "Cyhexatin". pubchem.ncbi.nlm.nih.gov.

[4] "Registration Review; Pesticide Dockets Opened for Review and Comment". US EPA. December 16, 2009. Retrieved 28 April 2023.

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