1067-33-0

Basic information

• Product Name: Dibutyltin diacetate
• Synonyms: Ba 2726;ba2726;bis(acetyloxy)dibutyl-stannan;Bis(acetyloxy)dibutylstannane;bis(acetyloxy)dibutyl-Stannane;Diacetoxybutyltin;Diacetoxydibutlyltin;diacetoxydibutyl-stannan
• CAS NO: 1067-33-0
• Molecular Formula: C₁₂H₂₄O₄Sn
• Molecular Weight: 351.03
• EINECS: 213-928-8
• Product Categories: Classes of Metal Compounds;Sn (Tin) Compounds;Typical Metal Compounds;organotin compound;Chemical Synthesis;Organometallic Reagents;Organotin;Organotins;Used for plastic heat stabilizer and organic silicon treating agent and curing agent;Pyridines
• Mol File: 1067-33-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 7-10 °C(lit.)
• Boiling Point: 142-145 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: colorless/liquid
• Density: 1.32 g/mL at 25 °C(lit.)
• Vapor Density: 12 (vs air)
• Vapor Pressure: 1.3 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.471(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 0.006g/l
• Water Solubility: insoluble
• BRN: 4136035
• CAS DataBase Reference: Dibutyltin diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Dibutyltin diacetate(1067-33-0)
• EPA Substance Registry System: Dibutyltin diacetate(1067-33-0)

Safety Data

• Hazard Codes: T,N,C
• Statements: 25-34-36/38-68-50/53-48/25-43-61-60
• Safety Statements: 26-36/37/39-45-37/39-28A-61-60-53
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• RTECS: WH6880000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1067-33-0(Hazardous Substances Data)

Usage

Chemical Properties

clear pale yellow to yellow liquid

Uses

Different sources of media describe the Uses of 1067-33-0 differently. You can refer to the following data:
1. PU catalyst, RTV silicone rubber
2. As as stabilizer in chlorinated organics, and as a catalyst for condensation reactions.Di-n-butyltin diacetate is used as a stabilizer for polyvinyl chloride. It acts as a catalyst for the preparation of silicone and urethane foams. Further, it is used as a curing agent for silicone elastomers. In addition to this, it is used as a precursor for thin-film tin(IV) oxide gas sensing materials by laser-assisted chemical vapor deposition.

General Description

Clear yellow liquid.

Air & Water Reactions

Forms white precipitate in water. Insoluble in water.

Reactivity Profile

Dibutyltin diacetate is stable under normal laboratory conditions. Dibutyltin diacetate may react with oxidizers. . Strongly reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents.

Fire Hazard

Dibutyltin diacetate is combustible.

Safety Profile

Poison by ingestion and intravenous routes. Experimental reproductive effects. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also TIN COMPOUNDS.

InChI:InChI=1/2C4H9.2C2H4O2.Sn/c2*1-3-4-2;2*1-2(3)4;/h2*1,3-4H2,2H3;2*1H3,(H,3,4);/q;;;;+2/p-2/rC8H18Sn.2C2H4O2/c1-3-5-7-9-8-6-4-2;2*1-2(3)4/h3-8H2,1-2H3;2*1H3,(H,3,4)/q+2;;/p-2

Synthetic route

(C4H9)2ISnCH(CH3)CH(CH3)O2CCH3 → (Z)-2-Butene (590-18-1) + iodoacetoxydibutylstannane + dibutyl tin diiodide (2865-19-2) + dibutyltin diacetate (1067-33-0)

Conditions	Yield
In neat (no solvent) heating at 50°C for a few hours; same result in CCl4 at 50°C;	A 100% B n/a C n/a D n/a

(C4H9)2ISnCH(CH3)CH(CH3)O2CCH3 → iodoacetoxydibutylstannane + trans-2-Butene (624-64-6) + dibutyl tin diiodide (2865-19-2) + dibutyltin diacetate (1067-33-0)

Conditions	Yield
In neat (no solvent) heating at 50°C for a few hours; same result in CCl4 at 50°C;	A n/a B 100% C n/a D n/a

tin tetraacetate (10581-60-9, 69475-44-1) + tetra-n-butyltin(IV) (1461-25-2) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
210°C, 10 h;	73.4%

dibutyltin chloride (683-18-1) + potassium acetate (127-08-2) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
With ethanol

dibutylstannane (1002-53-5) + acetic acid (64-19-7) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
In not given reaction at room temperature;;

dibutylstannane (1002-53-5) + acetic acid (64-19-7) → 1,2-bis(acetyloxy)tetrabutyldistannane (54460-73-0) + dibutyltin diacetate (1067-33-0)

Conditions	Yield
In not given reaction at room temperature;;
In not given reaction at room temperature;;

lead(IV) tetraacetate + di-n-butyldiphenyltin (6452-61-5) → diphenyllead(IV) diacetate (6928-68-3) + dibutyltin diacetate (1067-33-0)

Conditions	Yield
boiling for 6h;;

di(n-butyl)tin oxide (818-08-6) + acetic acid (64-19-7) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
dissoln. of Sn-compd. in excess acid;

Triacetoxybutylstannane (14764-54-6) + tributyltin acetate (56-36-0) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
at 180°C, 10 h;
at 250℃; for 0.5h; Product distribution / selectivity; Inert atmosphere;
at 180°C, 10 h;

(C4H9)2Sn(CH2CH(C6H5)OCOCH3)2 (125610-50-6) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
In neat (no solvent) byproducts: PhCH=CH2; thermal decompn.;

bis(2-acetoxyethyl)dibutyltin (125610-43-7) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
In neat (no solvent) Kinetics; byproducts: C2H4; decompn. (140°C, 3 h);

bis(2-acetoxy-2-methylethyl)dibutyltin (125610-51-7) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
In neat (no solvent) Kinetics; byproducts: CH3CH=CH2; thermal decompn. (80°C, 0.3 h);

(C4H9)2Sn(CH2CH(CF3)OCOCH3)2 (125610-52-8) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
In neat (no solvent) Kinetics; byproducts: CF3CH=CH2; thermal decompn.;

tri-n-butyl(3-methylbutyloxy)tin (660402-31-3) + 1,1,3,3-tetrabutyl-1,3-bis(3-methylbutyloxy)distannoxane (660402-29-9) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
at 155℃; for 5h; Product distribution / selectivity; Inert atmosphere;

1,1,3,3-tetrabutyl-1,3-bis(3-methylbutyloxy)distannoxane (660402-29-9) + acetic anhydride (108-24-7) → Triacetoxybutylstannane (14764-54-6) + dibutyltin diacetate (1067-33-0)

Conditions	Yield
at 200℃; Product distribution / selectivity; Inert atmosphere;
With acetic acid Industry scale;

tri-n-butyl(3-methylbutyloxy)tin (660402-31-3) + 1,1,3,3-tetrabutyl-1,3-bis(3-methylbutyloxy)distannoxane (660402-29-9) + acetic anhydride (108-24-7) → dibutyltin diacetate (1067-33-0) + tributyltin acetate (56-36-0)

Conditions	Yield
at 25℃; for 1h; Product distribution / selectivity; Inert atmosphere;

acetic anhydride (108-24-7) + 1,1,3,3-tetra-n-butyl-1,3-di(n-butyloxy)-distanoxane (34833-46-0) → Triacetoxybutylstannane (14764-54-6) + dibutyltin diacetate (1067-33-0)

Conditions	Yield
at 200℃; for 5.3h; Product distribution / selectivity;

dibutyl-bis(2-ethylbutyloxy)tin (819792-09-1) + Triacetoxybutylstannane (14764-54-6) + tributyltin acetate (56-36-0) → dibutyltin diacetate (1067-33-0)

Conditions	Yield
at 250℃; for 0.5h; Product distribution / selectivity; Inert atmosphere;

1,1,2,2-tetrabutyl-1,2-dichloro distannane (54460-70-7) → dibutyltin diacetate (1067-33-0)

dibutyltin chloride (683-18-1) → dibutyltin diacetate (1067-33-0)

dibutyltin diacetate (1067-33-0) + methyl(phenyl)phosphinic chloride (5761-97-7) → [Sn(C4H9)2(O2P(CH3)(C6H5))2] (166772-38-9)

Conditions	Yield
In toluene byproducts: CH3COCl, n-Bu2SnCl2; dry conditions; 2 d, room temp., excess of R2Sn(OAc)2; pptn., filtn., washing (PhMe, Et2O), driyng (vac.); elem. anal.;	97%
In toluene byproducts: CH3COCl, n-Bu2SnCl2; dry conditions; molar ratio R2Sn(OAc)2:chloride 1:2;
In neat (no solvent) byproducts: CH3COCl, n-Bu2SnCl2; dry conditions; molar ratio R2Sn(OAc)2:chloride 1:2;
In diethyl ether byproducts: CH3COCl, n-Bu2SnCl2; dry conditions; molar ratio R2Sn(OAc)2:chloride 1:2;

dibutyltin diacetate (1067-33-0) + methyl(phenyl)phosphinic chloride (5761-97-7) → Dibutylzinn-bis-diphenylphosphonat (10586-75-1)

Conditions	Yield
In toluene byproducts: CH3COCl; dry conditions; 2 d, room temp., excess of tin compound; pptn., filtn., washing (PhMe, Et2O), driyng (vac.); elem. anal.;	97%

dibutyltin diacetate (1067-33-0) + phenylytterbium iodide (26138-28-3) → di-n-butyldiphenyltin (6452-61-5)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran byproducts: [O(YbI)2]; soln. of Yb-compd. addn. (dropwise, under Ar, Schlenk flask) with Sn-compd., stirring (2-3 h), aq. HCl addn., extraction (ether), extracts drying (MgSO4);	96%

dibutyltin diacetate (1067-33-0) → tetra-n-butyltin(IV) (1461-25-2)

Conditions	Yield
With n-butyllithium In diethyl ether 0°C;	80%

dibutyltin diacetate (1067-33-0) + thioacetamide (62-55-5) → (C4H9)2Sn(CH3COO)2 * (thioacetamide)2 (200567-57-3)

Conditions	Yield
In acetone mixing solns. with stirring, heating (10 min); standing (2 h, 25°C), filtration, washing (2 x acetone, Et2O), drying (owen, 110°C, 6 h, then vac. desiccator); elem. anal.;	72%

dibutyltin diacetate (1067-33-0) + phenylacetylene (536-74-3) → 2-methyl-4-phenyloxazole (20662-90-2)

Conditions	Yield
With trimethylsilylazide In toluene for 4h; Time; Reflux;	66%

[2,2]bipyridinyl (366-18-7) + water (7732-18-5) + dibutyltin diacetate (1067-33-0) + iminodiacetic acid (142-73-4) → (di-n-butyltin(iminodiacetate)(H2O))2*2,2'-bipyridine (1198025-98-7)

Conditions	Yield
In ethanol; water Sn-compd. in EtOH added dropwise to a magnetically stirred iminodiaceticacid and 2,2'-bipyridine in H2O at room temp., stirred overnight, reflu xed for 6 h, cooled; elem. anal.;	64%

1,10-Phenanthroline (66-71-7) + water (7732-18-5) + dibutyltin diacetate (1067-33-0) + iminodiacetic acid (142-73-4) → (di-n-butyltin(iminodiacetate)(H2O))2*1,10-phenanthroline (1198026-01-5)

Conditions	Yield
In ethanol; water Sn-compd. in EtOH added dropwise to a magnetically stirred iminodiaceticacid and 1,10-phenanthroline in H2O at room temp., stirred overnight, r efluxed for 6 h, cooled; elem. anal.;	64%

2,2'-oxybis-acetic acid (110-99-6) + 1,10-Phenanthroline (66-71-7) + water (7732-18-5) + dibutyltin diacetate (1067-33-0) → [Sn(oxydiacetate)(1,10-phenanthroline)(H2O)2]

Conditions	Yield
In ethanol for 4h; Reflux;	64%

picoline (108-89-4) + 2,2'-oxybis-acetic acid (110-99-6) + water (7732-18-5) + dibutyltin diacetate (1067-33-0) → [(n-Bu)2Sn(oda)(4-pic)]2·2H2O

Conditions	Yield
In ethanol at 20℃; for 5h; pH=9 - 10; Reflux;	62%

phenylarsonic acid (98-05-5) + dibutyltin diacetate (1067-33-0) → (C4H9)2Sn[C6H5AsOHO2]2 (88652-66-8)

Conditions	Yield
In methanol Sn-complex and ligand were stirred in MeOH at room temp. for ca. 12 h; filtered, washed with EtOH, dried under vac. at 20°C for 10 h; elem. anal.;	60%

Pyridine-2,6-dicarboxylic acid (499-83-2) + water (7732-18-5) + dibutyltin diacetate (1067-33-0) → [(n-Bu)2Sn(pda)(H2O)]2

Conditions	Yield
With triethylamine In ethanol at 20℃; for 5h; pH=9 - 10; Reflux;	59%

dibutyltin diacetate (1067-33-0) → tributyltin acetate (56-36-0)

Conditions	Yield
270°C, 4 h;	56.2%
270°C, 4 h;	56.2%

2,2'-oxybis-acetic acid (110-99-6) + [2,2]bipyridinyl (366-18-7) + water (7732-18-5) + dibutyltin diacetate (1067-33-0) → [Sn(oxydiacetate)(2,2'-bipyridine)(H2O)2]

Conditions	Yield
In ethanol for 4h; Reflux;	56%

dimethylphosphinic acid (3283-12-3) + dibutyltin diacetate (1067-33-0) → di-n-butyltin dimethylphosphinate (43190-16-5)

Conditions	Yield
In benzene room temp., 2 d; pptn., filtn., washing (C6H6, Et2O), drying (vac.); elem. anal.;	54%

dibutyltin diacetate (1067-33-0) + 4'-isobutyl phenylacetylene (132464-91-6) → 4-(4-isobutylphenyl)-2-methyloxazole

Conditions	Yield
With trimethylsilylazide In toluene for 2h; Reflux;	35%

cyano(4-isobutylphenyl)methyl diethylphosphate + dibutyltin diacetate (1067-33-0) → 4-(4-isobutylphenyl)-2-methyloxazole

Conditions	Yield
With trimethylsilylazide In toluene for 2h; Reflux;	27%

1,10-decanedioic acid (111-20-6) + dibutyltin diacetate (1067-33-0) → C20H38O6Sn (1225070-99-4)

Conditions	Yield
With acetic acid In chlorobenzene at -15 - 120℃;

oxygen (80937-33-3) + dibutyltin diacetate (1067-33-0) → tin(IV) oxide

Conditions	Yield
In neat (no solvent) Ar as carrier gas; (110) Si wafers as substrate; prepn. by thermal chemical vapor deposition at 425-500°C;
In gaseous matrix dibutyltin diacetate reacted with O2, flow rate: 100 sccm using Ar carrier gas with 100 sccm, temp. 90 °C;

dibutylstannane (1002-53-5) + dibutyltin diacetate (1067-33-0) → 1,2-bis(acetyloxy)tetrabutyldistannane (54460-73-0)

Conditions	Yield
In not given
bis-triphenylphosphine-palladium(II) chloride In neat (no solvent) in a Schlenk tube under N2 mixing of Sn-compds., after 5 min addn. of catalyst and stirring at room temp. for 2 h; using resulting oil without further purifn., purity (>94%) monitored by (119)Sn-NMR;

Upstream product

• 1002-53-5 dibutylstannane 
• 64-19-7 acetic acid 
• 6452-61-5 di-n-butyldiphenyltin 
• 10581-60-9 tin tetraacetate 
• 1461-25-2 tetra-n-butyltin(IV) 
• 14764-54-6 Triacetoxybutylstannane 
• 56-36-0 tributyltin acetate 
• 660402-31-3 tri-n-butyl(3-methylbutyloxy)tin 
• 660402-29-9 1,1,3,3-tetrabutyl-1,3-bis(3-methylbutyloxy)distannoxane 
• 108-24-7 acetic anhydride 
• 34833-46-0 1,1,3,3-tetra-n-butyl-1,3-di(n-butyloxy)-distanoxane 
• 819792-09-1 dibutyl-bis(2-ethylbutyloxy)tin 
• 818-08-6 di(n-butyl)tin oxide 
• 683-18-1 dibutyltin chloride 

Downstream Products

• 54460-73-0 1,2-bis(acetyloxy)tetrabutyldistannane 
• 56-36-0 tributyltin acetate 
• 1461-25-2 tetra-n-butyltin(IV) 
• 6452-61-5 di-n-butyldiphenyltin 
• 88652-68-0 (C₄H₉)2Sn[C₆H₅POHO₂]2 
• 166772-38-9 [Sn(C₄H₉)2(O₂P(CH₃)(C₆H₅))2] 
• 10586-75-1 Dibutylzinn-bis-diphenylphosphonat 
• 660402-27-7 dibutyl-bis(3-methylbutyloxy)tin 
• 123-92-2 3-methyl-1-butyl acetate 
• 819792-09-1 dibutyl-bis(2-ethylbutyloxy)tin 
• 10031-87-5 acetic acid-(2-ethyl-butyl ester) 
• 1020100-82-6 tri-n-butyl-(2-ethylbutyloxy)tin 
• 20662-90-2 2-methyl-4-phenyloxazole 
• 2322-57-8 dibutylphenylstannyl bromide 

Relevant articles and documents

Process for Production of Alkyl Tin Alkoxide Compound, and Process for Production of Carbonic Acid Ester Using the Compound

The present invention provides a process for producing: a compound represented by XOR2; a dialkyl tin dialkoxide compound having one tin atom, two Sn—R1 bonds and two Sn—OR2 bonds; and/or a tetraalkyl dialkoxy distannoxane compound having one Sn—O—Sn bond, in which each tin atom of the tetraalkyl dialkoxy distannoxane compound has two Sn—R1 bonds and one Sn—OR2 bond, the process comprising reacting in the absence of a catalyst at least one alkyl tin compound selected from the group consisting of i) and ii) below: i) a dialkyl tin compound having one tin atom, two Sn—R1 (wherein R1 represents an alkyl group) bonds, and two Sn—OX bonds (wherein OX is a group in which HOX that is a conjugate acid of OX is a Bronsted acid having a pKa of from 0 to 6.8); andii) a tetraalkyl distannoxane compound having one Sn—O—Sn bond, in which each tin atom of the tetraalkyl distannoxane compound has two Sn—R1 bonds and one Sn—OX bond (wherein OX is a group in which HOX that is a conjugate acid of OX is a Bronsted acid having a pKa of from 0 to 6.8); anda carbonic acid ester represented by R2OCOOR2 (wherein R2 represents a linear or branched, saturated or unsaturated hydrocarbon group, a hydrocarbon group having a saturated or unsaturated cyclic hydrocarbon substituent, or a Y—CH2— group (wherein Y represents an alkyl polyalkylene group, an aromatic group or a cyclic saturated or unsaturated alkylene ether group)), and/oran alcohol represented by R2OH (wherein R2 is the same as defined above).

Reactions of Organoytterbium Compounds RYbI (R = Me, Et, Ph) with Organotin Oxides and Acetates

Reactions of RYbI (R = Me, Et, Ph) with organotin oxides and acetates) involve cleavage of the Sn-O bonds to form tetrasubstituted stannanes mostly as single or main reaction products (yields 65-96 percent). A similar results was obtained in reaction of PhYbI with diphenyltin sulfide (yield 93 percent). However, reactions of RYbI (R = Me, Et, Ph) with Bu2SnO, followed by hydrolysis of the reaction mixtures lead to hydroxystannanoxanes Bu2RSnOH in 66-75 percent yields.

Stereochemistry of the thermal decomposition of (2-(acyloxy)alkyl)triorganostannanes

The stereochemical study of the thermal decomposition of (2-(acyloxy)alkyl)triorganostannanes revealed an anti β-elimination of (acyloxy)triorganostannanes. The process is highly stereospecific and not perturbed by the presence of a possible internal chelation favoring syn elimination. It corresponds to an open transition state. Kinetics of β-elimination in cyclohexyl and norbornyl systems showed that the reaction is much more rapid with a 180° dihedral angle between the metal and the ester group than with a 60° angle between the two. Stabilization of the partial positive charge developed during the transition state occurs mainly through hyperconjugation effect.