ChemicalBook--->CAS DataBase List--->13356-08-6

13356-08-6

13356-08-6 Structure

13356-08-6 Structure
IdentificationBack Directory
[Name]

Fenbutatin oxide
[CAS]

13356-08-6
[Synonyms]

bendex
OSADAN
TORQUE
VENDEX
hexakis
osdaran
sd14114
ent27738
VENDEX(R)
TORQUE(R)
Vandex[R]
Neostanox
fenbutatin
FENBUTESTAN
Osadan(shell)
shellsd-14114
Fenbutatinoxid
FENBUTATIN OXIDE
fenbutatin-oxyde
fenylbutatinoxide
Trineophyltin Oxide
Fenbutatin oxide W.P.
Fenbutatin Oxide (>
Fenbutatin Oxide (>90%)
fenylbutylstanniumoxide
BIS(TRINEOPHYLTIN)OXIDE
Fenbutatin Oxide Standard
Fenbutatin oxide,suspension
FENBUTATIN-OXIDE, 1GM, NEAT
Fenbutatin-oxide(Technical)
CHLORSULFURON PESTANAL, 100 MG
fenbutatin-oxide (bsi,iso,jmaf)
BIS(TRINEOPHYLTIN)OXIDE, tech-95
Fenbutatin-oxide 1g [13356-08-6]
Fenbutatin oxide @100 μg/mL in Acetone
Bis(tris(β,β-dimethylphenethyl)tin)oxide
Bis[tri(2-methyl-2-phenylpropyl)tin]oxide
BIS[TRIS(2-METHYL-2-PHENYLPROPYL)]TIN OXIDE
Hexakis[β,β-dimethyl phenethyl] distannoxane
di(tri-(2,2-dimethyl-2-phenylethyl)tin)oxide
hexakis(2-methyl-2-phenylpropyl)-distannoxan
Hexakis(2-methyl-2-phenylpropyl)distannoxene
Distannoxane,hexakis(2-methyl-2-phenylpropyl)-
bis(tris(beta,beta-dimethylphenethyl)tin)oxide
HEXAKIS-(2-METHYL-2-PHENYLPROPYL)-DISTANNOXANE
Bis[tris(2-methyl-2-phenylpropyl)stannyl]oxide
hexakis(beta,beta-dimethylphenethyl)-distannoxan
hexakis(beta,beta-dimethylphenethyl)-distannoxane
1,1,1,3,3,3-Hexakis(2-Methyl-2-phenylpropyl)distannoxane
Distannoxane, 1,1,1,3,3,3-hexakis(2-methyl-2-phenylpropyl)-
fenbutatin oxide (ISO) bis(tris(2-methyl-2-phenylpropyl)tin)oxide
tris(2-methyl-2-phenylpropyl)-tris(2-methyl-2-phenylpropyl)stannyloxystannane
[EINECS(EC#)]

236-407-7
[Molecular Formula]

C60H78OSn2
[MDL Number]

MFCD00072480
[MOL File]

13356-08-6.mol
[Molecular Weight]

1052.68
Chemical PropertiesBack Directory
[Appearance]

White crystalline solid or powder. Mild odor
[Melting point ]

142-145°C
[Boiling point ]

235-240 °C(Press: 0.05 Torr)
[density ]

0.42 g/cm3
[vapor pressure ]

8.5×10-8 Pa (20 °C)
[Fp ]

100 °C
[storage temp. ]

APPROX 4°C
[solubility ]

Chloroform (Slightly), DMSO (Very Slightly, Heated, Sonicated)
[form ]

solid
[Water Solubility ]

0.005 mg l-1 (23 °C)
[Hydrolytic Sensitivity]

4: no reaction with water under neutral conditions
[Merck ]

13,3991
[Henry's Law Constant]

4.9×103 mol/(m3Pa) at 25℃, HSDB (2015)
[Major Application]

agriculture
environmental
[InChI]

InChI=1S/6C10H13.O.2Sn/c6*1-10(2,3)9-7-5-4-6-8-9;;;/h6*4-8H,1H2,2-3H3;;;
[InChIKey]

HOXINJBQVZWYGZ-UHFFFAOYSA-N
[SMILES]

[Sn](CC(C)(C1=CC=CC=C1)C)(CC(C)(C1=CC=CC=C1)C)(CC(C)(C1=CC=CC=C1)C)O[Sn](CC(C)(C1=CC=CC=C1)C)(CC(C)(C1=CC=CC=C1)C)CC(C)(C1=CC=CC=C1)C
[EPA Substance Registry System]

Distannoxane, hexakis(2-methyl-2-phenylpropyl)- (13356-08-6)
Hazard InformationBack Directory
[Chemical Properties]

White crystalline solid or powder. Mild odor
[Uses]

Fenbutatin Oxide is an organotin pesticide. Fenbutatin Oxide is widely used as an aracacide in the control of mites, in particular spider mites.
[Uses]

Acaricide.
[General Description]

White crystalline solid with a mild odor.
[Air & Water Reactions]

Insoluble in water.
[Reactivity Profile]

Fenbutatin oxide is in the family of tin compounds widely used as stabilizers for plastics, additives to paint(as antifouling agents). Some have catalytic properties. Examples include butyl tin, dibutyl tin oxide. Their main hazard is associated with their high toxicity, in skin adsorption or inhalation.
[Agricultural Uses]

Insecticide, Miticide: A U.S. EPA restricted Use Pesticide (RUP). A selective miticide for deciduous pome and stone fruits, citrus fruits, grapes, vegetables, berry fruit, nut crops (selected), ornamentals and greenhouse crops.
[Trade name]

BENDEX®; NEOSTANOX®; OSDARAN®; SD-14114®; SHELL SD-14114®; TORQUE®; VENDEX®
[Potential Exposure]

Organotin/phenyltin insecticide and selective miticide for deciduous pome and stone fruits, citrus fruits, grapes, vegetables, berry fruit, nut crops (selected), ornamentals, and greenhouse crops. A United States Environmental Protection Agency Restricted Use Pesticide (RUP)
[First aid]

Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
[Shipping]

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
[Incompatibilities]

May form explosive mixture with air. Decomposes above 230C. Contact with water causes slow decomposition. Orgotin oxides can be strongly basic and will react, possibly dangerously, with acidic compounds and mixtures
[Description]

Fenbutin oxide is an acaricide used to control a wide range of phytophagous mites and other insects although it is not now used in the developed world. It has a low aqueous solubility but is soluble in several organic solvents. This substance tends to be very persistent in soil and water systems. It is not highly volatile. Toxicity to fish is high but moderate to low for many other species. Fenbutin oxide has a low human oral toxicity but may be fatal if inhaled.
[Waste Disposal]

Organic tin compounds may be disposed of in sealed containers in secured sanitary landfill. Chemical Treatability of tin; Concentration Process: Chemical precipitation; Chemical Classification: Metals; Scale of Study: Pilot scale; Type of Wastewater Used: Synthetic wastewater; Results of Study: At 600 ppm, 95.3% reduction with alum. At 500 ppm, 98% reduction with ferric chloride, 92% reduction with lime (three coagulants used: 200 mg of alum at pH = 6.4, 40 ppm of ferric chloride @ pH = 6.2, 41 ppm of lime @ pH = 11.5 Chemical coagulation was followed by dual media filtration). Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
[Definition]

ChEBI: Fenbutatin oxide is an organotin acaricide.
[Production Methods]

Fenbutatin oxide is commercially produced through a multi-step synthesis involving organotin compounds. The process typically begins with tris(2-methyl-2-phenylpropyl)tin, which is reacted in an organic solvent like toluene under anhydrous conditions to prevent hydrolysis. A dehydrating agent is used to facilitate the formation of the distannoxane bridge, a key structural feature of fenbutatin oxide. The reaction mixture is heated and stirred to complete oxidation and condensation, followed by purification through filtration and solvent evaporation.
[Mechanism of action]

Selective, non-systemic with contact and stomach action, acts by inhibiting oxidative phosphorylation. Inhibitor of mitochondrial ATP synthase.
[Environmental Fate]

Chemical/Physical. Reacts with moisture forming tris(2-methyl-2-phenylpropyl)tin hydroxide (Worthing and Hance, 1991).
[Metabolic pathway]

Fenbutatin oxide is quite stable to hydrolytic degradation. Metabolism in soils, plants and animals is minimal. The extensive and irreversible adsorption/binding to cationic and organic matter is the primary dissipation mechanism in the soil environment. Cleavage of the neophenyl-tin linkages is the primary degradation and metabolic pathway (Scheme 1). Transformation of the neophenyl moiety has not been observed. Most of the information reported below was obtained from experiments using 119mSlna belhg conducted by DuPont.
[Degradation]

Fenbutatin oxide (1) dissociates slowly in water to the corresponding hydroxide [tris(2-methyl-2-phenylpropyl)tin hydroxide 21. The neophenyl moiety of fenbutatin oxide was stable at pH 5, 7, and 9 at 25 °C with minimal degradation occurring after 30 days (Home, 1987a).
The photodegradation of fenbutatin oxide in pH 7 buffer solution was a significant degradation process with a DT50 of approximately 51 days following continuous exposure to simulated sunlight at 25 °C (Home, 1987b). Fenbutatin oxide underwent hydrolysis with a loss of two moles of the 2-methyl-2-phenylprop yl moiety, yielding dlhydroxy-bis(2-methyl- 2-phenylpropyl)stannane (3), accounting for ca. 23% of the initial concentration after 15 days of continuous irradiation. Fenbutatin oxide and its metabolites react reversibly with water to form the analogous oxide/hydroxide compounds (Gray et a1 ., 1995).
[Pesticide Type]

Acaricide; Insecticide
Safety DataBack Directory
[Hazard Codes ]

Xn;N,N,Xn,T+
[Risk Statements ]

21-36/38-50/53-26
[Safety Statements ]

28-36/37-45-60-61
[RIDADR ]

UN 2811
[WGK Germany ]

3
[RTECS ]

JN8770000
[TSCA ]

Yes
[HazardClass ]

9
[PackingGroup ]

III
[Storage Class]

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
[Hazard Classifications]

Acute Tox. 2 Inhalation
Aquatic Acute 1
Aquatic Chronic 1
Eye Irrit. 2
Skin Irrit. 2
[Hazardous Substances Data]

13356-08-6(Hazardous Substances Data)
[Toxicity]

LD50 in rats, rabbits (mg/kg): >2000 orally; >2000 percutaneously (Zweig)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Hydrochloric acid-->Tetrahydrofuran-->Isopropyl alcohol-->Magnesium-->Xylene-->Tin-->Tin tetrachloride-->3-Chloro-2-methylpropene-->1-Chloropropane-->Neophyl chloride
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