4253-22-9

Basic information

• Product Name: DI-N-BUTYLTIN SULFIDE
• Synonyms: DI-N-BUTYLTIN SULFIDE;DIBUTYL TIN SULFIDE;bts71;bts80;dibutylthioxo-stannan;Dibutylthioxostannane;dibutylthioxo-Stannane;dibutylthioxo-ti
• CAS NO: 4253-22-9
• Molecular Formula: C₈H₁₈SSn
• Molecular Weight: 265
• EINECS: 224-220-3
• Mol File: 4253-22-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 90-98°C
• Boiling Point: >300°C
• Flash Point: °C
• Appearance: yellowish oily liquid
• Density: 1,42 g/cm3
• Refractive Index: 1.579
• CAS DataBase Reference: DI-N-BUTYLTIN SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DI-N-BUTYLTIN SULFIDE(4253-22-9)
• EPA Substance Registry System: DI-N-BUTYLTIN SULFIDE(4253-22-9)

Safety Data

• Statements: 20/21/22-25
• Safety Statements: 20-23-36/37/39-45
• RIDADR: 3146
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4253-22-9(Hazardous Substances Data)

Usage

Description

Dibutyltin Sulfide is a kind of sulfide. It can be used as a catalytic agent in some polymerization reaction. Dibutyltin sulfide has better catalytic activity and water-tolerant stability than DBTDL in waterborne polyurethane pre-polymerization system and can decrease the pre-polymerization time. It can also catalyze the ring-expansion polymerization of mesolactide. It is also an antioxidant and stabilizer for vinyl resins.

Sources

Chen, Cun You, T. W. Wang, and D. I. Chao. Electroplating & Finishing 30.10(2011):61-63. Gooch J.W. (2011) Dibutyltin Sulfide. In: Gooch J.W. (eds) Encyclopedic Dictionary of Polymers. Springer, New York, NY https://onlinelibrary.wiley.com/doi/full/10.1002/pola.28948

Safety Profile

Poison by ingestion. Mutation data reported. See also TIN COMPOUNDS and SULFIDES. When heated to decomposition it emits toxic fumes of SOx.

InChI:InChI=1/2C4H9.S.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3;;/rC8H18SSn/c1-3-5-7-10(9)8-6-4-2/h3-8H2,1-2H3

Synthetic route

(4R,5R)-2,2-di-n-butyl-4,5-dimethyl-1,3,2-dioxastannolane (5271-63-6) + phenyl isothiocyanate (103-72-0) → cis-4,5-dimethyl-N-phenyl-1,3-dioxolan-2-imine (132783-14-3) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
In 1,2-dichloro-ethane addn.of PhNCS to a soln. of the Sn-compound under N2; stirred at 40°C for 2 h; solvent was removed in vac.; column chromy. (silica gel; eluent: C6H6); vac. distn. (120°C/0.1 Torr);	A 100% B n/a
With triethylamine In 1,2-dichloro-ethane addn.of PhNCS to a soln. of the Sn-compound and Et3N under N2; stirred at 40°C for 0.5 h; solvent was removed in vac.; yield after column chromy. (silica gel; eluent: C6H6): 93%; vac. distn. (120°C/0.1 Torr);	A 100% B n/a

(4R,5R)-2,2-dibutyl-4,5-dimethyl-1,3,2-dioxastannolane (88341-32-6) + (4R,5R)-2,2-di-n-butyl-4,5-dimethyl-1,3,2-dioxastannolane (5271-63-6) + methyl thioisocyanate (556-61-6) → cis-4,5-dimethyl-N-methyl-1,3-dioxolan-2-imine (134110-59-1) + trans-4,5-dimethyl-N-methyl-1,3-dioxolan-2-imine (134110-60-4) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
In 1,2-dichloro-ethane addn.of PhNCS to a soln. of the Sn-compound under N2; stirred at 40°C for 1.0 h; solvent was removed in vac.; column chromy. (silica gel; eluent: C6H6); vac. distn.; elem. anal.; NMR; IR; mass spectra;	A 100% B 12% C n/a

(4R,5R)-2,2-dibutyl-4,5-dimethyl-1,3,2-dioxastannolane (88341-32-6) + (4R,5R)-2,2-di-n-butyl-4,5-dimethyl-1,3,2-dioxastannolane (5271-63-6) + butyl isothiocyanate (592-82-5) → cis-4,5-dimethyl-N-butyl-1,3-dioxolan-2-imine (132783-18-7) + trans-4,5-dimethyl-N-butyl-1,3-dioxolan-2-imine (134110-61-5) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
In 1,2-dichloro-ethane addn.of PhNCS to a soln. of the Sn-compound under N2; stirred at 40°C for 1.0 h; solvent was removed in vac.; column chromy. (silica gel; eluent: C6H6); vac. distn.; elem. anal.; NMR; IR; mass spectra;	A 100% B 10% C n/a

(4R,5R)-2,2-dibutyl-4,5-dimethyl-1,3,2-dioxastannolane (88341-32-6) + (4R,5R)-2,2-di-n-butyl-4,5-dimethyl-1,3,2-dioxastannolane (5271-63-6) + phenyl isothiocyanate (103-72-0) → cis-4,5-dimethyl-N-phenyl-1,3-dioxolan-2-imine (132783-14-3) + trans-4,5-dimethyl-N-phenyl-1,3-dioxolan-2-imine (132783-13-2) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
In 1,2-dichloro-ethane addn.of PhNCS to a soln. of the Sn-compounds under N2; stirred at 40°C for 1.0 h; solvent was removed in vac.; column chromy. (silica gel; eluent: C6H6); vac. distn.;	A 100% B 30% C n/a
In 1,2-dichloro-ethane addn.of PhNCS to a soln. of the Sn-compound under N2; stirred at 40°C for 7.0 h; solvent was removed in vac.; column chromy. (silica gel; eluent: C6H6); vac. distn.;	A 100% B 5% C n/a

4-tert-butyl-1,3-dioxa-2-stannolane-Bu2 (136094-77-4) → di-n-butyltinmercaptid (4253-22-9) + 4-tert-Butyl-1,3-dioxolane-2-thione (134110-52-4)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 5 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6); elem. anal.; NMR; IR;	A n/a B 91%

(4R,5R)-2,2-dibutyl-4,5-dimethyl-1,3,2-dioxastannolane (88341-32-6) + phenyl isothiocyanate (103-72-0) → trans-4,5-dimethyl-N-phenyl-1,3-dioxolan-2-imine (132783-13-2) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane addn.of PhNCS to a soln. of the Sn-compound and Et3N under N2; stirred at 40°C for 5.0 h; solvent was removed in vac.; column chromy. (silica gel; eluent: C6H6); vac. distn.;	A 82% B n/a
In 1,2-dichloro-ethane addn.of PhNCS to a soln. of the Sn-compound under N2; stirred at 40°C for 5.0 h; solvent was removed in vac.; column chromy. (silica gel; eluent: C6H6); vac. distn.;	A 65% B n/a

(4R,5R)-2,2-dibutyl-4,5-dimethyl-1,3,2-dioxastannolane (88341-32-6) + (4R,5R)-2,2-di-n-butyl-4,5-dimethyl-1,3,2-dioxastannolane (5271-63-6) → trans-4,5-dimethyl-1,3-dioxolane-2-thione (66841-50-7) + di-n-butyltinmercaptid (4253-22-9) + cis-4,5-Dimethyl-1,3-dioxolane-2-thione (56194-03-7)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 5 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6);	A 80% B n/a C 70%
With carbon disulfide In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound; stirred for 20 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6);	A <1 B n/a C <1

trans-4,5-hexahydrobenzo-1,3-dioxa-2-stannolane-Bu2 (5271-61-4, 5271-62-5, 83020-55-7, 97002-13-6, 125134-99-8) + cis-2,2-di-n-butyl-1,3,2-dioxacyclohexanestannolane (5271-62-5) → cis-Hexahydrobenzo<1,3>dioxol-2-thion (56155-84-1) + trans-4,5-hexahydrobenzo-1,3-dioxolane-2-thione (16166-55-5, 18462-86-7, 56155-84-1, 56155-91-0) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 7 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6);	A 77% B <1 C n/a

(4R,5R)-2,2-di-n-butyl-4,5-dimethyl-1,3,2-dioxastannolane (5271-63-6) → cis-2,3,7,8-tetramethyl-1,4,6,9-tetraoxaspiro{4.4}nonane (24472-01-3, 29882-37-9, 134175-77-2) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
With carbon disulfide In 1,2-dichloro-ethane heating with stirring at 100°C for 12 h; cooling; CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: n-hexane/benzene); vac. distn. (45°C/3 Torr); elem. anal.; NMR; mass spectra;	A 75% B n/a

4-methyl-1,3-dioxa-2-stannolane-Bu2 (3590-60-1) → 4-methyl-1,3-dioxolane-2-thione (13303-26-9) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 7 h at 50°C; excess CS2 and solvent were removed in vac.; yield after column chromy. (silica gel; eluent: C6H6) = 65 %;	A 71% B n/a

4-methoxymethyl-1,3-dioxa-2-stannolane-Bu2 (136094-78-5) → di-n-butyltinmercaptid (4253-22-9) + 2,7-Methoxymethyl-1,4,6,9-tetraoxaspiro<4.4>nonane (134110-58-0)

Conditions	Yield
With carbon disulfide In 1,2-dichloro-ethane heating with stirring at 100°C for 12 h; cooling; CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: n-hexane/benzene); vac. distn. (60°C/0.1 Torr); elem. anal.; NMR; mass spectra;	A n/a B 70%

(4R,5R)-2,2-dibutyl-4,5-dimethyl-1,3,2-dioxastannolane (88341-32-6) → trans-2,3,7,8-tetramethyl-1,4,6,9-tetraoxaspiro{4.4}nonane (134175-77-2) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
With carbon disulfide In 1,2-dichloro-ethane heating with stirring at 100°C for 12 h; cooling; CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: n-hexane/benzene); vac. distn. (50°C/2 Torr); elem. anal.; NMR; mass spectra;	A 69% B n/a

(+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan (61235-70-9) → di-n-butyltinmercaptid (4253-22-9) + 2,7-Diphenyl-1,4,6,9-tetraoxaspiro<4.4>nonane (134110-57-9)

Conditions	Yield
With carbon disulfide In 1,2-dichloro-ethane heating with stirring at 100°C for 12 h; cooling; CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: n-hexane/benzene); vac. distn. (170°C/0.1 Torr); elem. anal.; NMR; mass spectra;	A n/a B 65%

4-tert-butyl-1,3-dioxa-2-stannolane-Bu2 (136094-77-4) → di-n-butyltinmercaptid (4253-22-9) + 2,7-Di-tert-butyl-1,4,6,9-tetraoxaspiro<4.4>nonane (134110-56-8)

Conditions	Yield
With carbon disulfide In 1,2-dichloro-ethane heating with stirring at 100°C for 12 h; cooling; CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: n-hexane/benzene); vac. distn. (52°C/0.1 Torr); elem. anal.; NMR; mass spectra;	A n/a B 62%

4-ethyl-1,3-dioxa-2-stannolane-Bu2 (134110-54-6) → di-n-butyltinmercaptid (4253-22-9) + 2,7-Diethyl-1,4,6,9-tetraoxaspiro<4.4>nonane (134110-55-7)

Conditions	Yield
With carbon disulfide In 1,2-dichloro-ethane heating with stirring at 100°C for 12 h; cooling; CS2 and solvent were removed in vac.; yield after column chromy. (silica gel; eluent: n-hexane/benzene) and vac. distn. (100°C/2 Torr): 52%; elem. anal.; NMR; mass spectra;	A n/a B 60%

4-ethyl-1,3-dioxa-2-stannolane-Bu2 (134110-54-6) → di-n-butyltinmercaptid (4253-22-9) + 4-Ethyl-1,3-dioxolane-2-thione (134110-51-3)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 20 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6); NMR; elem. anal.;	A n/a B 56%

(+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan (61235-70-9) → di-n-butyltinmercaptid (4253-22-9) + 4-Phenyl-1,3-dioxolane-2-thione (116447-63-3)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 20 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6); elem. anal.; mass spectra; NMR; IR;	A n/a B 56%

(4R,5R)-2,2-dibutyl-4,5-dimethyl-1,3,2-dioxastannolane (88341-32-6) → trans-4,5-dimethyl-1,3-dioxolane-2-thione (66841-50-7) + di-n-butyltinmercaptid (4253-22-9)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 30 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6);	A 53% B n/a

(4R,5R)-2,2-di-n-butyl-4,5-dimethyl-1,3,2-dioxastannolane (5271-63-6) → di-n-butyltinmercaptid (4253-22-9) + cis-4,5-Dimethyl-1,3-dioxolane-2-thione (56194-03-7)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 5 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6);	A n/a B 46%

4-methoxymethyl-1,3-dioxa-2-stannolane-Bu2 (136094-78-5) → di-n-butyltinmercaptid (4253-22-9) + 4-(methoxymethyl)-1,3-dioxolane-2-thione (134110-53-5)

Conditions	Yield
With carbon disulfide; tributylphosphine In 1,2-dichloro-ethane under N2; CS2 was added to a soln. of the Sn-compound and Bu3P; stirred for 20 h at 50°C; excess CS2 and solvent were removed in vac.; column chromy. (silica gel; eluent: C6H6); elem. anal.; NMR; mass spectra; IR;	A n/a B 25%

1,1'-bis(chloromercurio)ferrocene + di-n-butyltinmercaptid (4253-22-9) → 1,1'-bis(di-n-butylchlorostannyl)ferrocene

Conditions	Yield
In toluene byproducts: HgS; (N2); refluxing the stirred soln. of Hg-complex; dropwise addn. of Sn-compound in hot toluene; refluxing for 3 h; cooling; filtration; evapn. of solv. (vac.); recrystn. from cyclohexane;	85%

1-(chloromercuri)ferrocene + di-n-butyltinmercaptid (4253-22-9) → di-n-butylchlorostannylferrocene

Conditions	Yield
In toluene byproducts: HgS; (N2); refluxing the stirred soln. of Hg-complex; dropwise addn. of Sn-compound in hot toluene; refluxing for 3 h; cooling; filtration; evapn. of solv. (vac.); recrystn. from cyclohexane;	85%

bis(ferrocenyl)mercury (1274-09-5) + di-n-butyltinmercaptid (4253-22-9) → di-n-butylstannyldiferrocene

Conditions	Yield
In 1,4-dioxane byproducts: HgS; (N2); refluxing the stirred soln. of Hg-complex; dropwise addn. of Sn-compound in hot dioxane; refluxing for 3 h; cooling; filtration; evapn. of solv. (vac.); recrystn. from benzene/ethanol;	82%

Upstream product

• 88341-32-6 (4R,5R)-2,2-dibutyl-4,5-dimethyl-1,3,2-dioxastannolane 
• 5271-63-6 (4R,5R)-2,2-di-n-butyl-4,5-dimethyl-1,3,2-dioxastannolane 
• 556-61-6 methyl thioisocyanate 
• 592-82-5 butyl isothiocyanate 
• 61235-70-9 (+/-)4-phenyl-2,2-di-n-butyl-1,3,2-dioxa stannolan 
• 136094-78-5 4-methoxymethyl-1,3-dioxa-2-stannolane-Bu₂ 
• 5271-61-4 trans-4,5-hexahydrobenzo-1,3-dioxa-2-stannolane-Bu₂ 
• 5271-62-5 cis-2,2-di-n-butyl-1,3,2-dioxacyclohexanestannolane 
• 136094-77-4 4-tert-butyl-1,3-dioxa-2-stannolane-Bu₂ 
• 134110-54-6 4-ethyl-1,3-dioxa-2-stannolane-Bu₂ 
• 3590-60-1 4-methyl-1,3-dioxa-2-stannolane-Bu₂ 
• 103-72-0 phenyl isothiocyanate 

Relevant articles and documents

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Urethane prepolymer

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