14814-09-6

Basic information

• Product Name: 3-Mercaptopropyltriethoxysilane
• Synonyms: (3-mercaptopropyl)triethoxy-silan;3-(triethoxysilyl)-1-propanethio;3-(triethoxysilyl)-propanethio;3-(triethoxysilyl)propylmercaptan;kh590;triethoxy(3-mercaptopropyl)silane;GAMMA-MERCAPTOPROPYLTRIETHOXYSILANE;3-TRIETHOXYSILYL-1-PROPANETHIOL
• CAS NO: 14814-09-6
• Molecular Formula: C₉H₂₂O₃SSi
• Molecular Weight: 238.42
• EINECS: 238-883-1
• Product Categories: Industrial/Fine Chemicals;Mercapto;Chloroalkylsilanes, etc. (Silane Coupling Agents);Functional Materials;Si (Classes of Silicon Compounds);Silane Coupling Agents;Si-O Compounds;Trialkoxysilanes;Adhesion Promoters;Coupling Agents;Mecapto Silanes;Surface Modifiers
• Mol File: 14814-09-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 210 °C
• Flash Point: 88°C
• Appearance: Clear to straw liquid with unpleasant odor of sulfide
• Density: 0.987 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0535mmHg at 25°C
• Refractive Index: 1.4331
• Storage Temp.: 2-8°C
• PKA: 10.39±0.10(Predicted)
• Water Solubility: Hydrolyzes slowly in water.
• Sensitive: Moisture Sensitive
• BRN: 2039575
• CAS DataBase Reference: 3-Mercaptopropyltriethoxysilane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Mercaptopropyltriethoxysilane(14814-09-6)
• EPA Substance Registry System: 3-Mercaptopropyltriethoxysilane(14814-09-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• WGK Germany: 3
• RTECS: TZ7760000
• F: 10-13
• TSCA: Yes
• PackingGroup: III
• Hazardous Substances Data: 14814-09-6(Hazardous Substances Data)

Usage

Introduction

3-Mercaptopropyltriethoxysilane is a bifunctional organosilane possessing a reactive organic mercapto and a hydrolyzable inorganic methoxysilyl group. 3-Mercaptopropyltriethoxysilane is a clear, colorless to light yellow liquid with a slightly mercaptan odor. It is soluble in alcohols, ketones and aliphatic or aromatic hydrocarbons. Applications: 3-Mercaptopropyltriethoxysilane can be used as coupling agent to improve the adhesion of sulfur cured elastomers (polysulfide, polyurethane sealants) to inorganic fillers (such as silica, clay, glass, mica and talc etc.), fiberglass and surfaces. Mineral-reinforced articles such as shoe soles, rubber rollers and wheels, white sidewalls, and wire and cable insulation also can be produced with lower silane loadings. Used to improve properties of mineral filled elastomer, including modulus, tensile and tear strength, heat buildup, abrasion resistance, resilience, compression set and cure time. Used as a pretreatment on minerals or added at the time of compounding. Used to improve low-rolling resistance in silica-reinforced tire tread compounds.

Chemical Properties

Clear to straw liquid with unpleasant odor of sulfide.

Uses

It can improve the properties of the mineral-filled elastomer, including modulus, tensile and tear strength, heat buildup, abrasion resistance, resilience. It can be used as a pretreatment on minerals or added at the time of compounding. Mineral-reinforced rubbers such as shoe soles, rollers, wheels, white sidewalls, wire and cable insulation are the common case (3-Mercaptopropyl)triethoxysilane, could be used in. It also finds it uses as an intermediate, in polymer and tire manufacture, and as a laboratory reagent.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C9H22O3SSi/c1-4-10-14(11-5-2,12-6-3)9-7-8-13/h13H,4-9H2,1-3H3

Synthetic route

(3-chloropropyl)triethoxysilane (5089-70-3) → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
With sodium hydrogen sulfide; sodium ethanolate; sodium iodide; N,N,N',N'-tetramethylguanidine In ethanol; N,N-dimethyl-formamide; butanone at 60 - 70℃; under 2625.26 Torr; for 6h; Temperature; Pressure; Autoclave; Inert atmosphere; Large scale;	95.4%
With sodium hydrogen sulfide; tetrabutylammomium bromide In ethanol at 80℃; for 5h; Temperature;	95.5%
With sodium sulfide; tetrabutylammomium bromide; water In toluene at 90 - 95℃; for 3h;	94.1%

prop-2-ene-1-thiol (870-23-5) + Triethoxysilane (998-30-1) → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
In tetrahydrofuran at 60 - 90℃; for 1.25h; Solvent; Temperature; Inert atmosphere;	88%

(3-chloropropyl)triethoxysilane (5089-70-3) → 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6)

Conditions	Yield
With sodium hydrogen sulfate; sodium hydrogensulfide; tetrabutylammomium bromide In water at 75℃; for 5.63333h;	A 84% B 2.7 %Chromat. C 0.7 %Chromat.
With sodium hydrogensulfide; sulfur; tetrabutylammomium bromide In water at 70 - 94℃; for 3h;	A 66.7 %Chromat. B 3.37 %Chromat. C 27.9 %Chromat.
With hydrogenchloride; sodium hydrogensulfide; tetrabutylammomium bromide In water at 65 - 70℃; under 760.051 Torr; for 5.25h;	A 91.0 %Chromat. B 1.99 %Chromat. C 2.34 %Chromat.

(3-chloropropyl)triethoxysilane (5089-70-3) → ethanol (64-17-5) + 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
With sodium hydrogensulfide; hydrogen sulfide; N-[bis(diethylamino)methylene]-N-ethylethane ammonium chloride In water at 98℃; under 879.175 - 1034.32 Torr; for 6h; Product distribution / selectivity;	A 1.06 %Chromat. B 74%
With sodium hydrogensulfide; hydrogen sulfide; tetrabutylammomium bromide In water at 98℃; under 1846.09 Torr; for 8h; Product distribution / selectivity;	A 2.9 %Chromat. B 66%

ethanol (64-17-5) + 3-(trimethoxysilyl)-1-propanethiol (4420-74-0) → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
With toluene-4-sulfonic acid

allyltriethoxysilane (2550-04-1) → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
With hydrogen sulfide Irradiation;

allyltriethoxysilane (2550-04-1) → 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6)

Conditions	Yield
With hydrogen sulfide under 760 Torr; for 2.5h; Irradiation; Yield given;

S-[3-(trimethoxysilyl)propyl] ethanethioate (64456-54-8) → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOMe / methanol 2: TsOH View Scheme

3-Chloropropyltrimethoxysilan (2530-87-2) → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2S, Na / methanol 2: TsOH View Scheme

(3-chloropropyl)triethoxysilane (5089-70-3) → 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5)

Conditions	Yield
With sodium hydrogensulfide; sodium acetate; tetrabutylammomium bromide In water	A 83.1 %Chromat. B 7.38 %Chromat.
Stage #1: (3-chloropropyl)triethoxysilane With sodium hydrogensulfide In ethanol; water at 50 - 110℃; for 3h; Heating / reflux; Stage #2: With formic acid In ethanol; water at 55℃; for 0.25h; Product distribution / selectivity;
With sodium hydrogensulfide; sodium hydrogencarbonate; potassium carbonate; sulfur In ethanol; water at 80℃; under 2625.26 Torr; for 1h; Product distribution / selectivity;

(3-chloropropyl)triethoxysilane (5089-70-3) → C14H32Cl2O5Si2 (158588-47-7) + C14H34O5S2Si2 + 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6)

Conditions	Yield
With sodium hydrogensulfide In ethanol at 90 - 100℃; for 2 - 4h; Conversion of starting material;

(3-chloropropyl)-diethoxy-chlorosilane (135795-91-4) + (3-chloropropyl)-ethoxy-dichlorosilane (87765-00-2) + ethanol (64-17-5) + 3-chloropropyltrichlorosilane (2550-06-3) + (3-chloropropyl)triethoxysilane (5089-70-3) → 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6)

Conditions	Yield
With sodium sulfide at 50 - 102℃; for 3h; Product distribution / selectivity;
With sodium hydrogensulfide at 50 - 111℃; for 4.25h; Conversion of starting material;
Stage #1: (3-chloropropyl)-diethoxy-chlorosilane; (3-chloropropyl)-ethoxy-dichlorosilane; ethanol; 3-chloropropyltrichlorosilane; (3-chloropropyl)triethoxysilane With sodium hydrogensulfide at 30 - 110℃; for 3.25h; Stage #2: With formic acid In ethanol at 50 - 57℃; for 0.25h; Conversion of starting material;

ethanol (64-17-5) + 3-chloropropyltrichlorosilane (2550-06-3) + (3-chloropropyl)triethoxysilane (5089-70-3) → C14H32Cl2O5Si2 (158588-47-7) + C14H34O5S2Si2 + 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6)

Conditions	Yield
With sodium hydrogensulfide at 90 - 100℃; for 2 - 4h; Conversion of starting material;

ethanol (64-17-5) + 3-chloropropyltrichlorosilane (2550-06-3) + (3-chloropropyl)triethoxysilane (5089-70-3) → 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6)

Conditions	Yield
With sodium sulfide at -10 - 120℃; under 2400.24 Torr; for 2 - 5.33333h; Product distribution / selectivity;
With sodium hydrogensulfide at 93 - 96℃; for 2h; Conversion of starting material;

Si 69 → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
With hydrogen; H 105 BA/W 5percent Ru at 172 - 173℃; under 46879.7 - 66756.7 Torr; for 6.66667 - 6.83333h; Product distribution / selectivity;
With hydrogen; H 105 BA/W 5percent Ru In 1,4-dioxane at 164 - 168℃; under 48004.8 - 66831.7 Torr; for 6.66667 - 6.85h; Product distribution / selectivity;

Si 266 → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
With hydrogen; CE 105R/W 5percentPd + 0.5percent Mo at 175℃; under 37503.8 Torr; for 9.9h; Product distribution / selectivity;
With hydrogen; B 111 W at 141℃; under 38253.8 Torr; for 4.2h; Product distribution / selectivity;
With hydrogen; CE 105 R/W 5percent Pd + 0.5percent Mo In cyclohexane at 157 - 167℃; under 37503.8 Torr; for 6 - 6.95h; Product distribution / selectivity;

4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
With hydrogen; E105Y/W 5percent Pd In ethanol at 155℃; under 38253.8 Torr; Product distribution / selectivity;
With hydrogen; CE 101 XR/W 5percent Pd + 1percent Sn In ethanol at 126℃; under 37503.8 Torr; for 0.916667h; Product distribution / selectivity;
With hydrogen; CE 105 XR/W 5percent Pd + 0.5percent Mo In ethanol at 154℃; under 37503.8 Torr; for 1.33333h; Product distribution / selectivity;
With hydrogen; E 105 XRS/W 5percent Pd; S doped In ethanol at 152℃; under 37503.8 Torr; for 2.28333h; Product distribution / selectivity;
With hydrogen; T-8027 (52percent Ni, doped with 2.4percent zirconium) In ethanol at 161 - 167℃; under 37503.8 Torr; for 2.03333 - 2.31667h; Product distribution / selectivity;

4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) → 3-Mercaptopropyltriethoxysilane (14814-09-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7)

Conditions	Yield
With hydrogen; T-8027 (52percent Ni, doped with 2.4percent zirconium) In ethanol at 159℃; under 37503.8 Torr; for 2.2h; Product distribution / selectivity;

bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + n-octanoic acid chloride (111-64-8) → 3-(octanoylsulfanyl)-1-propyltriethoxysilane (220727-26-4) + octanoic acid ethyl ester (106-32-1) + (3-chloropropyl)triethoxysilane (5089-70-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7)

Conditions	Yield
Stage #1: bis(3-triethoxysilylpropyl) tetrasulfide With sodium In Solvent 140 at 110℃; for 0.75h; Stage #2: n-octanoic acid chloride In Solvent 140 at 45 - 104℃; for 1h; Stage #3: With water In toluene at 45℃; Product distribution / selectivity;

...Expand

4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + n-octanoic acid chloride (111-64-8) → 3-(octanoylsulfanyl)-1-propyltriethoxysilane (220727-26-4) + octanoic acid ethyl ester (106-32-1) + (3-chloropropyl)triethoxysilane (5089-70-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7)

Conditions	Yield
Stage #1: 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane With sodium In toluene at 110℃; for 0.75 - 1.15h; Stage #2: n-octanoic acid chloride In toluene at 45 - 60℃; for 1 - 2h; Stage #3: With water In toluene at 45℃; Product distribution / selectivity;

C10H24N2O3SSi*ClH → 3-Mercaptopropyltriethoxysilane (14814-09-6)

Conditions	Yield
With sodium ethanolate; ethylenediamine at 80 - 90℃;	228 g

3-Mercaptopropyltriethoxysilane (14814-09-6) + allyl choline phosphate (77075-58-2) → C17H40NO7PSSi

Conditions	Yield
With benzophenone In ethanol at 20℃; for 0.25h; UV-irradiation; Inert atmosphere;	100%
In ethanol at 20℃; for 0.25h; UV-irradiation; Inert atmosphere;
With benzophenone In ethanol at 20℃; for 0.25h; Irradiation;

3-Mercaptopropyltriethoxysilane (14814-09-6) + 1,3,4,6-tetraallyl glycoluril (229162-26-9) → 1,3,4,6-tetrakis[3-[[3-(triethoxysilyl)propyl]thio]propyl]glycoluril

Conditions	Yield
With 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile at 30℃; for 6h;	100%

3-Mercaptopropyltriethoxysilane (14814-09-6) + N-(4-(allyloxy)phenyl)formamide (51515-21-0) → N-(4-(3-((3-triethoxysilyl)propylthio)propoxy)phenyl)formamide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 20℃; for 3.5h; Irradiation; Inert atmosphere; Schlenk technique;	100%

2-methyl-2,4-pentanediol (107-41-5) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → 3-(2-methyl-2,4-pentanedioxyethoxysilyl)-1-propanethiol

Conditions	Yield
toluene-4-sulfonic acid at 33 - 60℃; under 11 Torr; for 2h;	99.2%

ethenesulfonic acid ethyl ester (4058-26-8) + 3-Mercaptopropyltriethoxysilane (14814-09-6) + triethylamine (121-44-8) → C11H25O6S2Si(1-)*C8H20N(1+)

Conditions	Yield
In dichloromethane at 20℃; Cooling with ice;	99%

3-Mercaptopropyltriethoxysilane (14814-09-6) + tri-tert-butyl 2,2',2"-(10-allyl-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate → tri-tert-butyl 2,2',2"-(10-(3-((3-(triethoxysilyl)propyl)thio)propyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran at 20℃; for 72h; Inert atmosphere; Schlenk technique; UV-irradiation;	99%

(3-chloropropyl)triethoxysilane (5089-70-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5)

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane; 3-Mercaptopropyltriethoxysilane at 60℃; for 2h; Stage #2: With sodium ethanolate In ethanol at 65℃; for 2h; Temperature;	98%

3-Bromophenol (591-20-8) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → C15H26O4SSi

Conditions	Yield
With C12H17O2Si(1-)*C29H45P*Pd(2+)*Br(1-); triethylamine In tert-butyl alcohol at 20℃; for 24h;	98%

PVS (5535-48-8) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → triethoxy (3-(2-(phenylsulfonyl)ethylthio)propyl)silane

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at 20℃; for 29h;	97%

3-Mercaptopropyltriethoxysilane (14814-09-6) + limonene. (138-86-3) → (3-((2-(4-methylcyclohex-3-en-1-yl)propan-2-yl)thio)propyl)triethoxysilane

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6.5h; Inert atmosphere;	97%
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6h; Inert atmosphere;	97%
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6h; Inert atmosphere;	97%

3-Mercaptopropyltriethoxysilane (14814-09-6) + limonene. (138-86-3) → (3-((2-(4-methyl-3-((3-(triethoxysilyl)propyl)thio)cyclohexyl)propan-2-yl)thio)propyl)triethoxysilane

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6h; Inert atmosphere;	97%

3-Mercaptopropyltriethoxysilane (14814-09-6) + N-methacryloyloxyethyl-N,N-dimethylammonium-α-N-methylcarboxybetaine (62723-61-9) → C19H39NO7SSi

Conditions	Yield
With triethylamine In ethanol at 20℃; for 24h;	96%

4-ethenylcyclohexene (100-40-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → (3-((2-(cyclohex-3-en-1-yl)ethyl)thio)propyl)triethoxysilane

Conditions	Yield
In toluene at 70℃; for 6.5h; Inert atmosphere;	96%
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6h; Inert atmosphere;	95%

anthracenylmethyl chloride (24463-19-2) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → 3-[(anthracen-10-yl)methylthio]propyltriethoxysilane (1239599-24-6)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	95%

2,4,4-trimethyl-1-pentene (107-39-1) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → triethoxy(3-((2,4,4-trimethylpentyl)thio)propyl)silane

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 60℃; for 3h; Inert atmosphere;	95%

3-Mercaptopropyltriethoxysilane (14814-09-6) + 1,6-dichlorohexane (2163-00-0) → 1-chloro-6-thiopropyltriethoxysilylhexane + 1,6-bis(thiopropyltriethoxysilyl) hexane

Conditions	Yield
Stage #1: 3-Mercaptopropyltriethoxysilane With sodium ethanolate In ethanol at 20℃; for 3h; Reflux; Stage #2: 1,6-dichlorohexane In ethanol at 80℃; for 3.5h; Reflux;	A 95% B 5%

3-Mercaptopropyltriethoxysilane (14814-09-6) + N-(4-(undec-10-en-1-yloxy)phenyl)formamide → N-(4-((11-((3-(triethoxysilyl)propyl)thio)undecyl)oxy)phenyl) formamide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In chloroform at 20℃; for 24h; Irradiation; Schlenk technique; Inert atmosphere;	95%

1-benzoylpyrrolidine-2,5-dione (6343-27-7) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → S-(3-(triethoxysilyl)propyl) benzothioate

Conditions	Yield
With potassium carbonate In toluene at 100℃; for 16h; Schlenk technique;	94%

formaldehyd (50-00-0) + 2,6-di-tert-butylphenol (128-39-2) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → 4-((3-(triethoxysilyl)propylthio)methyl)-2,6-di-tert-butylphenol

Conditions	Yield
With 2,6-di-tert-butyl-4-(dimethylaminomethyl)phenol In N,N-dimethyl-formamide at 120℃; for 4h;	93%

1-chloro-3,6,9-trioxadecane (52995-76-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → C16H36O6SSi

Conditions	Yield
With sodium methylate In tetrahydrofuran at 0 - 20℃; for 2.83333h; Heating / reflux;	93%
Stage #1: 3-Mercaptopropyltriethoxysilane With sodium methylate In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: 1-chloro-3,6,9-trioxadecane In tetrahydrofuran at 0 - 20℃; for 2.66667h; Heating / reflux;	93%

3-Mercaptopropyltriethoxysilane (14814-09-6) + 1,3-bis[4-(3-butenyloxy)-2,6-diisopropylphenyl]imidazolium chloride (1620922-80-6) → 1,3-bis[4-(4-{[3-(triethoxysilyl)propyl]thio}butyloxy)-2,6-diisopropylphenyl]imidazolium chloride (1620922-82-8)

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In ethanol for 24h; Inert atmosphere; Schlenk technique; Irradiation;	93%
With 2,2-bis(hydroxymethyl)propionic acid In ethanol at 20℃; for 24h; Schlenk technique; UV-irradiation; Inert atmosphere;

3-Mercaptopropyltriethoxysilane (14814-09-6) + isopropenylbenzene (98-83-9) → triethoxy(3-((2-phenylpropyl)thio)propyl)silane

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 60℃; for 3h; Inert atmosphere;	93%

3-(tert-butyloxycarbonylamino)propionic acid (3303-84-2) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → C17H35NO6SSi

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 5 - 20℃;	93%

Beta-pinene (177698-19-0) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → C19H38O3SSi

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 60℃; for 3h; Inert atmosphere;	92%

2-Methyl-1-pentene (763-29-1) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → triethoxy(3-((2-methylpentyl)thio)propyl)silane

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 60℃; for 3h; Inert atmosphere;	92%

N-methylmaleimide (930-88-1) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → 2,5-pyrrolidinedione, 1-methyl-3-[[3-(triethoxysilyl)propyl]thio]- (1459802-39-1)

Conditions	Yield
With triethylamine In ethanol at 20℃; for 2.5h;	91%

(E)-β-farnesene (18794-84-8) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → C33H68O6S2Si2

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 60℃; for 3h; Inert atmosphere;	91%

1-[(2-bromo-2-methylpropionyl)oxy]-2-propene (40630-82-8) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → 3-(3-(triethoxysilyl)propylthio)propyl 2-bromo-2-methylpropanate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 3h; Inert atmosphere;	91%

3-Mercaptopropyltriethoxysilane (14814-09-6) → 3-triethoxysilyl-propylsulfanyl-trimethylsilane

Conditions	Yield
With chloro-trimethyl-silane; triethylamine In Petroleum ether	90.3%

Upstream product

• 5089-70-3 (3-chloropropyl)triethoxysilane 
• 40372-72-3 bis(3-triethoxysilylpropyl) tetrasulfide 
• 111-64-8 n-octanoic acid chloride 
• 56706-10-6 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane 
• 58505-59-2 C₁₀H₂₄N₂O₃SSi*ClH 
• 870-23-5 prop-2-ene-1-thiol 
• 998-30-1 Triethoxysilane 
• 2530-87-2 3-Chloropropyltrimethoxysilan 
• 64456-54-8 S-[3-(trimethoxysilyl)propyl] ethanethioate 
• 2550-04-1 allyltriethoxysilane 
• 64-17-5 ethanol 
• 4420-74-0 3-(trimethoxysilyl)-1-propanethiol 
• 2550-06-3 3-chloropropyltrichlorosilane 
• 135795-91-4 (3-chloropropyl)-diethoxy-chlorosilane 

Downstream Products

• 220727-26-4 3-(octanoylsulfanyl)-1-propyltriethoxysilane 
• 106-32-1 octanoic acid ethyl ester 
• 5089-70-3 (3-chloropropyl)triethoxysilane 
• 60764-86-5 bis-[γ-(triethoxysilyl)propyl]sulfide 
• 56706-10-6 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane 

Relevant articles and documents

ELECTRONIC SPECTRA AND ELECTRONIC STRUCTURE OF TRIALKOXYSILYLALKANETHIOLS

The ultraviolet absorption spectra of solutions of trialkoxysilylalkanethiols (RO)3Si(CH2)nSH (R=CH3, C2H5; n=1, 2, 3) and also of CH3Si(OC2H5)3 and C2H5Si(OC2H5)2 in heptane and acetonitrile were obtained in the region of 4.0-5.3x106 m-1.Analysis of the obtained photoelectron spectra of the triorganosilylalkanethiols X3Si(CH2)nSH (X=CH3, OCH3; n=1, 3) showed that the first photo-ionization potentials of the trialkoxysilylalkanethiols are lower than the values for the corresponding methyl derivatives.This is due to the participation of the n electrons of the oxygen atom of the methoxyl groups in destabilization of the highest occupied molecular orbital.An empirical and quantumchemical interpretation of the obtained spectra is given.

Synthesis method of 3- mercaptopropyltrialkoxysilane (by machine translation)

The, invention belongs, to the technical, field of coupling agent synthesis, 3 - and belongs to 10%-15% the technical field of coupling agent synthesis, 3 - 3 . (by machine translation)

Preparation method of mercaptopropyl alkoxysilane

The invention relates to a preparation method of mercaptopropyl alkoxysilane, and belongs to the field of organic fine chemical industry. The preparation method comprises the following steps: dissolving anhydrous sodium sulfide into an alcohol solvent, dropwise adding an acetic acid solution to convert the sodium sulfide solution into an alcohol solution of sodium hydrosulfide, and then reacting with chloropropyl alkoxysilane under the action of a phase transfer catalyst to produce the mercaptopropyl alkoxysilane, sodium chloride and sodium acetate; firstly primarily distilling an obtained crude product at low-temperature negative pressure to distill out the alcohol solvent and completely separate out the sodium chloride and sodium acetate, then performing filtering separation, and then rectifying an obtained filtrate to obtain a mercaptopropyl alkoxysilane product. The obtained mercaptopropyl alkoxysilane product has the content being higher than 99.0% and the yield being higher than95%; compared with other synthesis methods, the preparation method provided by the invention has the advantages of a high product content, a high yield, easy obtainment of raw materials, simple synthesis steps, no guanidinium salt byproducts, no use of a dangerous hydrogen sulfide raw material and the like.