2273-43-0

Basic information

• Product Name: Butyltin oxide
• Synonyms: BUTYLENESTANNONIC ACID;BUTYLTINHYDROXIDE-OXIDE;BUTYLTIN(IV) HYDROXIDE OXIDE;BUTYLSTANNOIC ACID;N-BUTYLSTANNOIC ACID;N-BUTYLTIN HYDROXIDE OXIDE;N-BUTYLTIN SESQUIOXIDE;1-butanestannonicacid
• CAS NO: 2273-43-0
• Molecular Formula: C₄H₁₀O₂Sn
• Molecular Weight: 208.83
• EINECS: 218-880-1
• Product Categories: Alkyl Metals;Classes of Metal Compounds;Grignard Reagents & Alkyl Metals;Sn (Tin) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;organotin compound;as powder coating catalyzer producing by polyester resin;Used in powder coating of saturated polyester resin synthesis, also used for polyester plasticizer, unsaturated polyester resin, alkyd resin
• Mol File: 2273-43-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 350 °C
• Appearance: White powder
• Density: 1,46 g/cm3
• Vapor Pressure: 24.4Pa at 25℃
• Storage Temp.: Store below +30°C.
• Solubility: 9.5mg/L in organic solvents at 20 ℃
• Water Solubility: 317-3200μg/L at 20℃
• Sensitive: Hygroscopic
• CAS DataBase Reference: Butyltin oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Butyltin oxide(2273-43-0)
• EPA Substance Registry System: Butyltin oxide(2273-43-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• RIDADR: 3146
• RTECS: WH6770000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2273-43-0(Hazardous Substances Data)

Usage

Chemical Properties

White infusible solid. Sol in Me 2 CO.

Uses

Esterification catalyst

Hazard

A poison.

Flammability and Explosibility

Notclassified

Safety Profile

A poison by intravenous route. See also TIN COMPOUNDS. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C4H9.H2O.O.Sn/c1-3-4-2;;;/h1,3-4H2,2H3;1H2;;/q;;;+1/p-1/rC4H10O2Sn/c1-2-3-4-7(5)6/h5H,2-4H2,1H3

Synthetic route

ammonium hydroxide (1336-21-6) + Trichlorbutylstannan (1118-46-3) + sodium carbonate (497-19-8) → n-butylstannoic acid (2273-43-0)

Conditions	Yield
In water at 60℃; for 2.5h; Temperature;	99.4%

Trichlorbutylstannan (1118-46-3) + sodium hydroxide (1310-73-2) → n-butylstannoic acid (2273-43-0)

Conditions	Yield
With chitosan modified imidazoline amphoteric surfactant; quaternized polyvinyl alcohol In octanol at 90℃; for 4h; Reagent/catalyst;	62%

n-butylstannoic acid (2273-43-0) + 2-phenoxyacetic acid (122-59-8) → [(C4H9Sn(O2CCH2OC6H5)O)6] (929680-99-9)

Conditions	Yield
In benzene refluxed for 12 h (equimol., Dean-Stark); cooled, filtered, evapd. to dryness;	99%

(C60C(C(O)OCH2C6H3(OC16H33)2)C(O)OCH2C(O)OCH2)2C6H3OCH2CO2H + n-butylstannoic acid (2273-43-0) → [SnO(C4H9)((C60C(C(O)OCH2C6H3(OC16H33)2)C(O)OCH2C(O)OCH2)2C6H3OCH2CO2)]6

Conditions	Yield
In benzene refluxed for 12 h (equimol., Dean-Stark); cooled, filtered, evapd. to dryness;	99%

C60C(C(O)OCH2C6H3(OC16H33)2)C(O)OCH2CO2H (929680-97-7) + n-butylstannoic acid (2273-43-0) → Sn6O6(12+)*6C4H9(1-)*6C60C(C(O)OCH2C6H3(OC16H33)2)C(O)OCH2CO2(1-)=[SnO(C4H9)(C104H73O8)]6

Conditions	Yield
In benzene refluxed for 12 h (equimol., Dean-Stark); cooled, filtered, evapd. to dryness;	99%

C60(C(C(O)OCH2C6H3(OC16H33)2)C(O)OCH2)2C6H3OCH2CO2H + n-butylstannoic acid (2273-43-0) → Sn6O6(12+)*6C4H9(1-)*6C60(C(C(O)OCH2C6H3(OC16H33)2)C(O)OCH2)2C6H3OCH2CO2(1-)=[SnO(C4H9)(C154H151O15)]6

Conditions	Yield
In benzene refluxed for 12 h (equimol., Dean-Stark); cooled, filtered, evapd. to dryness;	99%

ortho-nitrobenzoic acid (552-16-9) + n-butylstannoic acid (2273-43-0) → n-butyloxotin o-nitrobenzoate hexamer * 3C6H6

Conditions	Yield
With C6H6 In dichloromethane; benzene byproducts: H2O; addn. of Sn-acid to a stirred soln. of CH2Cl2 and benzene, addn. of benzoic acid, reflux for 18 h, removal of H2O azeotropically, cream-white cloidy suspn., standing for 24 h; filtration of white powder, washing with benzene, standing gives larger crystals, drying; elem. anal.;	98%

thiobenzoic acid (98-91-9) + n-butylstannoic acid (2273-43-0) → [(butyl)Sn(O)(thiobenzoate)]2 (869111-73-9)

Conditions	Yield
In benzene soln. of thiobenzoic acid added to suspn. of Sn compd. at 28 °C, stirred for 2 h; solvent evapd. under reduced pressure, dried at 0.05 Torr and 28 °C, recrystd. by slow cooling of hot acetone soln.; elem. anal.;	98%

2,5-dimethylbenzenesulfonic acid (609-54-1) + water (7732-18-5) + n-butylstannoic acid (2273-43-0) → [(n-BuSn)12(μ3-O)14(μ2-OH)6][2,5-Me2C6H3(SO3)2]2

Conditions	Yield
In toluene mixt. of Sn compd. and aq. soln. of sulfonic acid (16.10:5.37 molar ratio) refluxed in toluene for 72 h (Dean-Stark apparatus); filtered, evapd., elem. anal.;	96%

diphenyl hydrogen phosphate (838-85-7) + n-butylstannoic acid (2273-43-0) → {(C4H9Sn(OH)O2P(OC6H5)2)3O}(1+)*{O2P(OC6H5)2}(1-)={(C4H9Sn(OH)O2P(OC6H5)2)3O}{O2P(OC6H5)2} (115270-33-2)

Conditions	Yield
In benzene soln. of diphenyl phosphate and n-butylstannoic acid in benzene (standing at 25°C, 48 h), removal of solvent (<20°C), addn. of diethyl ether, standing (25°C, 48 h), filtration from insol. material; removal of solvent (20°C); no successful purifn. from traces of water and other impurities, purity about 96 %;	95%

water (7732-18-5) + n-butylstannoic acid (2273-43-0) + benzenesulfonic acid (98-11-3) → [(n-BuSn)12(μ3-O)14(μ2-OH)6][C6H5(SO3)]2

Conditions	Yield
In water; toluene mixt. of Sn compd. and aq. soln. of sulfonic acid (8.62:2.87 molar ratio) refluxed in toluene for 72 h (Dean-Stark apparatus); filtered, evapd., elem. anal.;	95%

4-diphenylphosphanobenzoic acid (2129-31-9) + n-butylstannoic acid (2273-43-0) + toluene (108-88-3) → [(n-butyl)Sn(O)O2C-C6H4-p-PPh2]6*2(toluene)

Conditions	Yield
In toluene byproducts: water; reflux of ((n-Bu)Sn(O)OH)(n) and p-(diphenylphosphino)benzoic acid in toluene for 6 h with using Dean-Stark apparatus; filtration, evapn., recrystn., elem. anal.;	95%

1-Adamantanecarboxylic acid (828-51-3) + n-butylstannoic acid (2273-43-0) → [n-BuSn(O)OCO-Ad]6

Conditions	Yield
In neat (no solvent, solid phase) byproducts: H2O; Sn-compound and ligand were grinded at room temp. for 30 min; CH2Cl2 was added, filtered, evapd.;	93%
In toluene byproducts: H2O; mixt. of Sn-compound and ligand in toluene was heated under reflux for 6h; filtered, evapd.;	83%

tert-butylphosphonic acid (4923-84-6) + n-butylstannoic acid (2273-43-0) → [(n-Bu)2Sn2O[O2P(OH)-t-Bu]4]2 (124358-16-3)

Conditions	Yield
In neat (no solvent, solid phase) byproducts: H2O; Sn-compound and ligand were grinded at room temp. for 120 min; CH2Cl2 was added, filtered, evapd.;	92%

diphenyl-phosphinic acid (1707-03-5) + n-butylstannoic acid (2273-43-0) → [[n-BuSn(OH)O2PPh2]3O][O2PPh2]

Conditions	Yield
In neat (no solvent, solid phase) byproducts: H2O; Sn-compound and ligand were grinded at room temp. for 40 min; CH2Cl2 was added, filtered, evapd.;	91%
In toluene byproducts: H2O; refluxing n-butylstannoic acid with diphenylphosphinic acid in toluene (4 h); removing H2O azeotropically, removing solvent, addn. of Et2O, heating, filtration, crystn. from the filtrate; elem. anal.;	90%

ferrocenecarboxylic acid (1271-42-7) + n-butylstannoic acid (2273-43-0) → (C4H9Sn(O)OC(O)(C5H4)Fe(C5H5))6*2.57CHCl3

Conditions	Yield
In benzene byproducts: H2O; heated under reflux for 6 h; filtered, solvent removed in vacuo, elem. anal.;	91%

ferrocenecarboxylic acid (1271-42-7) + n-butylstannoic acid (2273-43-0) → [n-BuSn(O)OCOCH2Fc]6

Conditions	Yield
In neat (no solvent, solid phase) byproducts: H2O; Sn-compound and ligand were grinded at room temp. for 50 min; CH2Cl2 was added, filtered, evapd.;	91%

2-(5-ferrocenyl-3-(fluoromethyl)-1H-pyrazol-1-yl)acetic acid (1311994-24-7) + n-butylstannoic acid (2273-43-0) → [nBuSnO(trifuoromethyl-5-ferrocenyl-pyrazol-1-yl-acetate)]6

Conditions	Yield
In benzene to benzene soln. of Fc-compd. nBuSnO(OH) added under N2, reflux, overnight; solvent removed (reduced pressure); XRD, elem. anal.;	91%

ethylphosphonic acid (6779-09-5) + n-butylstannoic acid (2273-43-0) → {(C4H9)2Sn2O(O2P(OH)C2H5)4}2

Conditions	Yield
In acetone byproducts: H2O; phosphonic acid soln., addn. of stannonic acid; CHCl3 added, soln. filtered, evapd.; elem. anal.;	90%

benzoyl(thiobenzoyl)methane (1215-43-6) + n-butylstannoic acid (2273-43-0) → 2,4-bis{benzoyl(thiobenzoyl)methanato-O,S}-2,4-dibutyl-1,3,2λ(5),4λ(5)-dithiadistannetane (128243-41-4)

Conditions	Yield
In benzene byproducts: H2O; added S-compound to suspn. of butylstannoic acid; refluxed for 4 h, water was removed azeotropically,; evapd.; treated with acetone;	90%

ferrocenecarboxylic acid (1271-42-7) + n-butylstannoic acid (2273-43-0) → [n-BuSn(O)OCOFc]6

Conditions	Yield
In neat (no solvent, solid phase) byproducts: H2O; Sn-compound and ligand were grinded at room temp. for 60 min; CH2Cl2 was added, filtered, evapd.;	90%

thiobenzoic acid (98-91-9) + n-butylstannoic acid (2273-43-0) → butyltin tris(thiobenzoate)

Conditions	Yield
In dichloromethane byproducts: H2O; (anhydrous conditions); stirring (1-12 h); solvent removal (reduced pressure), drying (vac.), recrystn. (Et2O or CH2Cl2); elem. anal.;	90%

mesitylenecarboxylic acid (480-63-7) + n-butylstannoic acid (2273-43-0) → 6C4H9SnO(1+)*6(CH3)3C6H2CO2(1-)=[C4H9SnO(CO2C6H2(CH3)3)]6

Conditions	Yield
In benzene byproducts: H2O; mixt. of Sn-compound and ligand in benzene was heated under reflux for 6h under N2; filtered, solvent was removed in vacuo; elem. anal.;	89.6%

5-(4-carboxyphenyl)-10,15,20-tritolyl-21H,23H-porphyrin + n-butylstannoic acid (2273-43-0) → 6H2(C5H2N)4(C6H4CH3)3C6H4CO2(1-)*6Sn(4+)*6O(2-)*6C4H9(1-)=(H2(C5H2N)4(C6H4CH3)3C6H4CO2Sn(O)C4H9)6

Conditions	Yield
In benzene refluxed for 6 h;	89%

9-Anthracenecarboxylic acid (723-62-6) + n-butylstannoic acid (2273-43-0) → [n-BuSn(O)(O2C-9-anthracenyl)]6

Conditions	Yield
In toluene for 6h; Reflux; Dean-Stark;	89%

naphth-1-yl acetic acid (86-87-3) + n-butylstannoic acid (2273-43-0) → [n-BuSn(O)(O2C-CH2-1-naphthyl)]6

Conditions	Yield
In toluene for 6h; Reflux; Dean-Stark;	88%

xanthene-9-carboxylic acid (82-07-5) + n-butylstannoic acid (2273-43-0) → [n-BuSn(O)(O2C-9-xanthenyl)]6

Conditions	Yield
In toluene for 6h; Reflux; Dean-Stark;	88%

n-butylstannoic acid (2273-43-0) + cyclopropanecarboxylic acid (1759-53-1) → hexameric n-butyloxotin cyclopropanoate (115270-30-9)

Conditions	Yield
In benzene byproducts: water; addn. of (cyclo-CH2CH2CH)COOH to n-butylstannoic acid in dry benzene, heating (reflux, 4 h), removal of water (azeotropic distn., Dean-Stark app.); removal of solvent (vac.), soln. of solid in hot benzene/hexane, keeping in the refrigerator; elem. anal.;	86.7%

ferroceneacetic acid (1287-16-7) + n-butylstannoic acid (2273-43-0) → 6C4H9SnO(1+)*6C5H5FeC5H4CH2CO2(1-)=[C4H9SnO(CO2CH2C5H4FeC5H5)]6

Conditions	Yield
In benzene byproducts: H2O; mixt. of Sn-compound and Fe-complex in benzene was heated under reflux for 6 h under N2; filtered, solvent was removed in vacuo; elem. anal.;	86.7%

n-butylstannoic acid (2273-43-0) + benzoic acid (65-85-0) → hexameric n-butyloxotin benzoate (115270-31-0)

Conditions	Yield
In benzene byproducts: water; addn. of C6H5COOH to n-butylstannoic acid in dry benzene, heating (reflux, 4 h), removal of water (azeotropic distn., Dean-Stark app.); removal of solvent (vac.), soln. of solid in hot benzene/hexane, keeping in the refrigerator; elem. anal.;	85.4%
In benzene heated under Dean-Stark condns.;

para-xylene (106-42-3) + n-butylstannoic acid (2273-43-0) + anthranilic acid (118-92-3) → C66H90N6O18Sn6*C8H10

Conditions	Yield
Stage #1: n-butylstannoic acid; anthranilic acid In toluene for 8h; Reflux; Dean-Stark; Stage #2: para-xylene In toluene Dean-Stark;	85%

Upstream product

• 1336-21-6 ammonium hydroxide 
• 1118-46-3 Trichlorbutylstannan 
• 497-19-8 sodium carbonate 
• 1310-73-2 sodium hydroxide 

Downstream Products

• 116052-70-1 tetrameric n-butyloxotin dibenzylphosphinate 
• 1461-25-2 tetra-n-butyltin(IV) 
• 115270-33-2 {(C₄H₉Sn(OH)O₂P(OC₆H₅)2)3O}⁽¹⁺⁾*{O₂P(OC₆H₅)2}^(1-)={(C₄H₉Sn(OH)O₂P(OC₆H₅)2)3O}{O₂P(OC₆H₅)2} 
• 116076-45-0 dimeric n-butyloxotin bis(dicyclohexylphosphinate) 
• 109890-41-7 tetrameric n-butyloxotin dicyclohexylphosphinate 
• 869111-73-9 [(butyl)Sn(O)(thiobenzoate)]2 
• 868851-89-2 ([(n-BuSn)3(μ3-O)(OC6H4-4-I)3]2[HPO3]4) 
• 868851-87-0 ([(n-BuSn)3(μ3-O)(OC6H4-4-Cl)3]2[HPO3]4) 
• 115270-31-0 hexameric n-butyloxotin benzoate 
• 115270-29-6 hexameric n-butyloxotin cyclobutanoate*2 benzene 
• 116184-79-3 4Sn⁽⁴⁺⁾*4O^(2-)*4C₄H₉^(1-)*4OP(S)(C₆H₅)2^(1-)={C₄H₉Sn(O)SOP(C₆H₅)2}4 
• 116184-77-1 {(C₄H₉Sn)2OH(O₂P(C₆H₅)2)3(OSP(C₆H₅)2)2}2*8C₆H₆ 

Relevant articles and documents

Preparation method of monobutyltin oxide

The invention provides a preparation method of monobutyltin oxide. The method includes the steps of firstly, adding tetrabutyl tin into a reactor, evenly stirring, slowly dropwise adding tin tetrachloride, then stirring for 30 minutes, heating to 140 DEG C, and performing heat-preservation reaction for 4-8 hours to obtain the mixed solution of monobutyltin trichloride and dibutyltin dichloride; secondly, heating the mixed solution of the monobutyltin trichloride and the dibutyltin dichloride to 95-100 DEG C, and collecting the monobutyltin trichloride; thirdly, adding the monobutyltin trichloride collected in the second step, surfactant and an organic solvent into a reactor, evenly stirring, slowly dropwise adding a sodium hydroxide solution, then heating to 90 DEG C, performing heat-preservation reaction for 3.5-4 hours, cooling to room temperature, filtering to obtain crude monobutyltin oxide, washing the crude monobutyltin oxide until the crude monobutyltin oxide is neutral, and performing reduced-pressure drying at 80 DEG C for 12 hours to obtain the monobutyltin oxide, wherein the surfactant is chitosan modified imidazoline ampholytic surfactant and quaternized polyvinyl alcohol.