900-95-8

Basic information

• Product Name: Fentin acetate
• Synonyms: FENTIN ACETATE;BATASAN(R);BRESTAN;BRESTAN(R);ACETOXY-TRIPHENYLSTANNANE;TPTA;TRIPHENYLACETOXYTIN;TRIPHENYLTIN(IV) ACETATE
• CAS NO: 900-95-8
• Molecular Formula: C₂₀H₁₈O₂Sn
• Molecular Weight: 409.07
• EINECS: 212-984-0
• Product Categories: HERBICIDE;organotin compound;Agro-Products;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 900-95-8.mol

Chemical Properties

• Melting Point: 118-122°C
• Boiling Point: 60 °C
• Appearance: white/Powder
• Density: 1.55
• Vapor Pressure: 1.9 x 10-3 Pa (60 °C)
• Storage Temp.: APPROX 4°C
• Water Solubility: 28 mg/L (20 ºC)
• Merck: 14,9745
• CAS DataBase Reference: Fentin acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Fentin acetate(900-95-8)
• EPA Substance Registry System: Fentin acetate(900-95-8)

Safety Data

• Hazard Codes: T+;N,N,T+
• Statements: 24/25-26-37/38-40-41-48/23-50/53-63
• Safety Statements: 26-28-36/37/39-45-60-61
• RIDADR: 3146
• RTECS: WH6650000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 900-95-8(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Fentin acetate is used as a fungicide for controlling early and late blight in potatoes, as well as a range of diseases in vegetables, sugar beet, peanuts, wheat, coffee, cocoa, and pecans. Its protective and curative properties make it a valuable asset in maintaining crop health and productivity.
Used in Rice Fields:
Fentin acetate is used as an algaecide and molluscicide in rice fields, helping to control the growth of algae and snails that can negatively impact crop yields and quality.
Used in Marine Paints:
Fentin acetate has been used as an antifoulant in marine paint, preventing the growth of marine organisms on the surfaces of boats and other structures in contact with water. This helps to reduce drag and maintain the efficiency and longevity of these structures.

Air & Water Reactions

Slowly oxidized, hydrolyzed when exposed to air and moisture.

Reactivity Profile

ACETOXYTRIPHENYLSTANNANE is subject to decomposition when exposed to air, light and moisture [EPA, 1998].

Health Hazard

Very toxic, irritant to skin.

Fire Hazard

Avoid air, light and moisture.

Safety Profile

Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic by skin contact. Questionable carcinogen with experimental neoplastigenic data. An experimental teratogen. Other experimental reproductive effects. A fungicide and algicide used as a wood preservative. When heated to decomposition it emits acrid smoke and Sn' fumes. See also TIN COMPOUNDS.

Metabolic pathway

Fentin is degraded in soil and other biological media to give inorganic tin via the di- and mono-phenyltin compounds; often the resulting benzene is liberated. An extensive review on the metabolism and fate and behaviour of triphenyltin and its degradation products was published by Bock (1981). Fentin hydroxide has been the subject of an evaluation by the Pesticide Safety Directorate of UK MAFF (PSD, 1990).

Degradation

Fentin acetate is stable when dry but easily hydrolysed to fentin hydroxide in the presence of water. It is unstable in acids and alkalis (DT50 <3 hours at pH 5, 7 or 9; 22 °C) and ionises to the triphenyltin cation. Triphenyltin compounds are converted rapidly and quantitatively into the hydroxide by alkali. Diphenyltin compounds (2) (see Scheme 1) react similarly but the hydroxide quickly loses water forming the oxide. Diphenyltin chloride initially hydrolyses to (C6H5),Sn(OH)Cl which forms compound 3 when dissociated and then the oxide is formed via dimeric intermediates. Diphenyltin compounds also split off phenyl groups as benzene (4) under the influence of water, acids or bases. Monophenyltin compounds (5) are also converted by alkali into the hydroxide which immediately loses water to form phenylstannonic acid (C6H5SnOOH) (6). In aqueous solution and at room temperature, triphenyltin compounds decompose at a slow rate, losing phenyl groups as benzene. The acetate is decomposed by sunlight and atmospheric oxygen. Phenyltin compounds are slowly decomposed by sunlight and more rapidly by UV light to give inorganic tin via the di- and mono-phenyltin compounds (PM; Bock, 1981).

InChI:InChI=1/3C6H5.C2H4O2.Sn/c3*1-2-4-6-5-3-1;1-2(3)4;/h3*1-5H;1H3,(H,3,4);/q;;;;+1/p-1/rC18H15Sn.C2H4O2/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2(3)4/h1-15H;1H3,(H,3,4)/q+1;/p-1

Synthetic route

triphenylstannane (892-20-6) + acetic acid (64-19-7) → triphenyltin acetate (900-95-8)

Conditions	Yield
In n-heptane reaction of excess (C6H5)3SnH on refluxing for 3 h;;	85%
In not given reaction at 70°C for 0.5 h;;	17%

acetic acid (64-19-7) + triphenyl tin-hydroxide → triphenyltin acetate (900-95-8)

triphenylstannane (892-20-6) + tributyllead acetate (2587-82-8) → triphenyltin acetate (900-95-8)

Conditions	Yield
In not given byproducts: (C2H5)3PbH;

triphenyl(4-t-butylphenoxo)tin(IV) (159113-64-1) → triphenyltin acetate (900-95-8)

Conditions	Yield
With acetic acid In benzene mixt. refluxed, resulting solid washed with petroleum ether; resulting solid washed with petroleum ether, dried under reduced pressure, elem. anal.;

(CO)3CrC6H5Sn(C6H5)3 (42441-88-3) → triphenyltin acetate (900-95-8)

Conditions	Yield
With acetic acid
With CH3COOH

acetic acid (64-19-7) + (Z)-1-ethoxy-2-triphenylstannylethene (17421-63-5, 17421-65-7) → triphenyltin acetate (900-95-8) + ethyl vinyl ether (109-92-2)

Conditions	Yield
In chloroform-d1 Kinetics; (Ar); addn. of a soln. of acetic acid in CDCl3 to a soln. of tin compd. in CDCl3 at room temp.; detected by NMR;

acetic acid (64-19-7) + (E)-1-ethoxy-2-triphenylstannylethene (17421-65-7, 17421-63-5) → triphenyltin acetate (900-95-8) + ethyl vinyl ether (109-92-2)

Conditions	Yield
In chloroform-d1 Kinetics; (Ar); addn. of a soln. of acetic acid in CDCl3 to a soln. of tin compd. in CDCl3 at room temp.; detected by NMR;

acetic acid-(2-triphenylstannyl-ethyl ester) (19464-46-1) → triphenyltin acetate (900-95-8)

Conditions	Yield
In neat (no solvent) byproducts: CH2CH2; decomposition above 180 °C;;
In neat (no solvent) byproducts: CH2CH2; decomposition above 180 °C;;
Multi-step reaction with 2 steps 1: water 2: CH3COOH / neat (no solvent) View Scheme

(C6H5)3SnCH(CH3)CH(CH3)OH (24509-93-1) → triphenyltin acetate (900-95-8)

Conditions	Yield
With acetic acid In methanol Kinetics; byproducts: CH3CHCHCH3;
With acetic acid In methanol Kinetics; byproducts: CH3CHCHCH3;

(C6H5)3SnCH2C(CH3)2OH (23604-58-2) → triphenyltin acetate (900-95-8)

Conditions	Yield
With acetic acid In methanol Kinetics; byproducts: CH2C(CH3)2;
With acetic acid In methanol Kinetics; byproducts: CH2C(CH3)2;

2-triphenylstannyl-ethanol (23604-56-0) → triphenyltin acetate (900-95-8)

Conditions	Yield
With acetic acid In neat (no solvent) Kinetics; byproducts: CH2CH2, H2O; reaction with CH3COOH in presence of HClO4;;
With CH3COOH In neat (no solvent) Kinetics; byproducts: CH2CH2, H2O; reaction with CH3COOH in presence of HClO4;;

Acetyltriphenyllstannan (6430-26-8) → triphenyltin acetate (900-95-8)

Conditions	Yield
With oxygen
With O2

(C6H5)3SnCH2CH(OH)CH3 (23604-57-1) → triphenyltin acetate (900-95-8)

Conditions	Yield
With acetic acid In methanol Kinetics; byproducts: CH2CHCH3, H2O;
With acetic acid In methanol Kinetics; byproducts: CH2CHCH3, H2O;

acetic acid (64-19-7) + (Z)-1-ethylthio-2-triphenylstannylethene (351500-76-0, 351500-77-1) → triphenyltin acetate (900-95-8) + vinyl ethylsulfide (627-50-9)

Conditions	Yield
In chloroform-d1 Kinetics; (Ar); addn. of a soln. of acetic acid in CDCl3 to a soln. of tin compd. in CDCl3 at room temp.; detected by NMR;

acetic acid (64-19-7) + (E)-1-ethylthio-2-triphenylstannylethene (351500-77-1, 351500-76-0) → triphenyltin acetate (900-95-8) + vinyl ethylsulfide (627-50-9)

Conditions	Yield
In chloroform-d1 Kinetics; (Ar); addn. of a soln. of acetic acid in CDCl3 to a soln. of tin compd. in CDCl3 at room temp.; detected by NMR;

acetic acid (64-19-7) + Dimethyl-((Z)-2-phenyl-2-triphenylstannanyl-vinyl)-amine → (E)-N,N-dimethyl-2-phenylethen-1-amine (14846-39-0) + triphenyltin acetate (900-95-8)

Conditions	Yield
In chloroform-d1 Kinetics; (Ar); addn. of a soln. of acetic acid in CDCl3 to a soln. of tin compd. in CDCl3 at room temp.; detected by NMR;

acetic acid (64-19-7) + (Z)-1-ethoxy-2-triphenylstannylhex-1-ene (351500-72-6, 351500-73-7) → 1-ethoxy-hex-1-ene (14092-07-0) + triphenyltin acetate (900-95-8)

Conditions	Yield
In chloroform-d1 Kinetics; (Ar); addn. of a soln. of acetic acid in CDCl3 to a soln. of tin compd. in CDCl3 at room temp.; detected by NMR;

acetic acid (64-19-7) + (E)-1-ethoxy-2-triphenylstannylhex-1-ene (351500-73-7, 351500-72-6) → 1-ethoxy-hex-1-ene (14092-07-0) + triphenyltin acetate (900-95-8)

Conditions	Yield
In chloroform-d1 Kinetics; (Ar); addn. of a soln. of acetic acid in CDCl3 to a soln. of tin compd. in CDCl3 at room temp.; detected by NMR;

β-methoxycarbonyl ethyl triphenyltin(IV) (19464-43-8) → triphenyltin acetate (900-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / ethanol 2: CH3COOH / neat (no solvent) View Scheme

2-(2-triphenylstannylethyl)-4,4,6-trimethyl-1,3,2-dioxaborinan (26274-73-7) → triphenyltin acetate (900-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O2 / ethanol; sodium hydroxide 2: CH3COOH / neat (no solvent) View Scheme

bis(triphenylstannyl)magnesium (34666-89-2) → triphenyltin acetate (900-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: CH3COCl 2: O2 View Scheme

triphenylstannane (892-20-6) → triphenyltin acetate (900-95-8)

Conditions	Yield
Multi-step reaction with 3 steps 2: H2O2 / ethanol; sodium hydroxide 3: CH3COOH / neat (no solvent) View Scheme
Multi-step reaction with 2 steps 2: CH3COOH / neat (no solvent) View Scheme
Multi-step reaction with 2 steps 2: neat (no solvent) View Scheme
Multi-step reaction with 3 steps 2: water 3: CH3COOH / neat (no solvent) View Scheme
Multi-step reaction with 3 steps 2: KOH / ethanol 3: CH3COOH / neat (no solvent) View Scheme

lithium triphenylstannide (4167-90-2) → triphenyltin acetate (900-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,2-dimethoxyethane 2: CH3COOH / neat (no solvent) View Scheme
Multi-step reaction with 2 steps 1: CH3COCl / tetrahydrofuran 2: O2 View Scheme

sodium triphenylstannide → triphenyltin acetate (900-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: CH3COOH / neat (no solvent) View Scheme
Multi-step reaction with 2 steps 1: 1,2-dimethoxyethane 2: acetic acid / methanol View Scheme
Multi-step reaction with 2 steps 1: 1,2-dimethoxyethane 2: acetic acid / methanol View Scheme
Multi-step reaction with 2 steps 1: 1,2-dimethoxyethane 2: acetic acid / methanol View Scheme

triphenyltin acetate (900-95-8) + aluminum isopropoxide (555-31-7) → Ph3SnOAl(OPri)2 (138977-01-2)

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;	98%
In toluene exclusion of moisture, heated, isopropylacetate fractionated out continuously from 80°C to the boiling point of toluene; excess of toluene distd. off under reduced pressure; elem. anal.;	95%

indium(I) bromide + N,N,N,N,-tetramethylethylenediamine (110-18-9) + triphenyltin acetate (900-95-8) → Ph3SnIn(OAc)Br N,N,N',N'-tetramethylethanediamine adduct

Conditions	Yield
In toluene The suspn. of InX and Ph3SnX in toluene was cooled to -20°C, diamine was added stirring was continued for about 1 h; allowed to warm to room temp. for 1-2 h (N2 atm.);; filtered, solid was washed with toluene and dried in vac. at room temp.; elem. anal.;;	98%

N-(benzoyl)-N'-(ferrocenylidene)hydrazine + triphenyltin acetate (900-95-8) → (C6H5)2Sn(C5H5FeC5H4CHNNCO(C6H5))2

Conditions	Yield
In benzene equimolar amt. of educts refluxed in benzene for about 8 h; hot mixt. was filtered, filtrate concd. under vac. at 50°C, recrystd. from either benzene or chloroform, dried in vac., elem. anal.;	95%

indium chloride + N,N,N,N,-tetramethylethylenediamine (110-18-9) + triphenyltin acetate (900-95-8) → Ph3SnIn(OAc)Cl N,N,N',N'-tetramethylethanediamine adduct

Conditions	Yield
In toluene The suspn. of InX and Ph3SnX in toluene was cooled to -20°C, diamine was added stirring was continued for about 1 h; allowed to warm to room temp. for 1-2 h (N2 atm.);; filtered, solid was washed with toluene and dried in vac. at room temp.; elem. anal.;;	94%

indium iodide + N,N,N,N,-tetramethylethylenediamine (110-18-9) + triphenyltin acetate (900-95-8) → Ph3SnIn(OAc)I N,N,N',N'-tetramethylethanediamine adduct

Conditions	Yield
In toluene The suspn. of InX and Ph3SnX in toluene was cooled to -20°C, diamine was added stirring was continued for about 1 h; allowed to warm to room temp. for 1-2 h (N2 atm.);; filtered, solid was washed with toluene and dried in vac. at room temp. recrysd. from THF-MeOH; elem. anal.;;	92%

triphenyltin acetate (900-95-8) → hexaphenylditin (1064-10-4)

Conditions	Yield
In N,N-dimethyl acetamide Electrolysis; supporting electrolite LiClO4; filtration, washing with methanol then ether;	91%

C5H5FeC5H4CHNNHC(O)C6H4NO2 (402731-31-1) + triphenyltin acetate (900-95-8) → (C6H5)2Sn(C5H5FeC5H4CHNNCO(C6H4NO2))2

Conditions	Yield
In benzene equimolar amt. of educts refluxed in benzene for about 8 h; hot mixt. was filtered, filtrate concd. under vac. at 50°C, recrystd. from either benzene or chloroform, dried in vac., elem. anal.;	90%

(C5H5)Fe(C5H4CHNNHCOC6H4Cl) + triphenyltin acetate (900-95-8) → (C6H5)3Sn(C5H5FeC5H4CHNNCO(C6H4Cl)) (87854-63-5)

Conditions	Yield
In benzene equimolar amt. of educts refluxed in benzene for about 8 h; hot mixt. was filtered, filtrate concd. under vac. at 50°C, recrystd. from either benzene or chloroform, dried in vac., elem. anal.;	85%

formyl ferrocene-2-isonicotinoyl hydrazone + triphenyltin acetate (900-95-8) → (C6H5)2Sn(C5H5FeC5H4CHNNCO(C5H4N))2

Conditions	Yield
In benzene equimolar amt. of educts refluxed in benzene for about 8 h; hot mixt. was filtered, filtrate concd. under vac. at 50°C, recrystd. from either benzene or chloroform, dried in vac., elem. anal.;	80%

C5H5FeC5H4CHNNHC(O)C6H4OH + triphenyltin acetate (900-95-8) → (C6H5)2Sn(C5H5FeC5H4CHNNCO(C6H4OH))2

Conditions	Yield
In benzene equimolar amt. of educts refluxed in benzene for about 8 h; hot mixt. was filtered, filtrate concd. under vac. at 50°C, recrystd. from either benzene or chloroform, dried in vac., elem. anal.;	78%

sodium piperazine-N,N'-bisdithiocarboxylate (877-78-1, 7564-73-0) + triphenyltin acetate (900-95-8) → [(triphenyltin(IV))2 piperazine bis(dithiocarbamate)] (77347-72-9)

Conditions	Yield
In ethanol byproducts: NaCH3COO; in a dry box flushed with N2; mixing an alc. soln. of dithiocarbamate with an alc. soln. of Sn-compd.; filtering off the ppt., washing with alc. and drying in vac.; elem. anal.;	70%

bis(acetylacetonate)nickel(II) + water (7732-18-5) + triphenyltin acetate (900-95-8) → [Ni((CH3CO)2CH)2((C6H5)3SnOH)]2

Conditions	Yield
In tetrahydrofuran Sonication; sonicating (room temp., 30 min); filtering, crystn. on concg. and n-hexane addn. (-20°C, overnight); elem. anal.;	70%

sodium N,N-diethyldithiocarbamate (148-18-5) + triphenyltin acetate (900-95-8) → (C6H5)3Sn(S2CN(C2H5)2) (1803-18-5)

Conditions	Yield
In ethanol; chloroform byproducts: NaCH3COO; in a dry box flushed with N2; mixing an alc./CHCl3 soln. of dithiocarbamate with Sn-compd. in alc., stirring for ca 2 h; elem. anal.;	60%

borane (13283-31-3) + triphenyltin acetate (900-95-8) + ethanolamine (141-43-5) → phenylboronic acid (98-80-6) + 2-aminoethoxydiphenyl borate (15614-89-8)

Conditions

Yield

With water In tetrahydrofuran; diethyl ether; ethanol to THF soln. of Sn compd. added BH3 (N2, room temp.),refluxed (1 h), added H2O,stirred (30 min),extd. (Et2O), dried (MgSO4),evapd. in vac.,heated with pentane,filtered PhB(OH)2,filtrate evapd.,added Et2O,EtOH soln. of HOCH2CH2NH2 added,refluxed (30 min); filtered hot, complex pptd. by cooling, filtered; PhB(OH)2 recrystd. from H2O; compds. identified by m. p., IR, NMR;

Upstream product

• 64-19-7 acetic acid 
• 892-20-6 triphenylstannane 
• 2587-82-8 tributyllead acetate 
• 159113-64-1 triphenyl(4-t-butylphenoxo)tin(IV) 
• 42441-88-3 (CO)3CrC₆H₅Sn(C₆H₅)3 
• 17421-63-5 (Z)-1-ethoxy-2-triphenylstannylethene 
• 17421-65-7 (E)-1-ethoxy-2-triphenylstannylethene 
• 19464-46-1 acetic acid-(2-triphenylstannyl-ethyl ester) 
• 24509-93-1 (C₆H₅)3SnCH(CH₃)CH(CH₃)OH 
• 23604-58-2 (C₆H₅)3SnCH₂C(CH₃)2OH 
• 23604-57-1 (C₆H₅)3SnCH₂CH(OH)CH₃ 
• 351500-76-0 (Z)-1-ethylthio-2-triphenylstannylethene 
• 351500-77-1 (E)-1-ethylthio-2-triphenylstannylethene 
• 351500-72-6 (Z)-1-ethoxy-2-triphenylstannylhex-1-ene 

Downstream Products

• 1064-10-4 hexaphenylditin 
• 98-80-6 phenylboronic acid 
• 15614-89-8 2-aminoethoxydiphenyl borate 
• 138977-01-2 Ph₃SnOAl(OPrⁱ)₂ 
• 1803-18-5 (C₆H₅)3Sn(S₂CN(C₂H₅)2) 
• 87854-63-5 (C₆H₅)3Sn(C₅H₅FeC₅H₄CHNNCO(C₆H₄Cl)) 
• 77347-72-9 [(triphenyltin(IV))2 piperazine bis(dithiocarbamate)] 

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