(3-Mercaptopropyl)trimethoxysilane

(3-Mercaptopropyl)trimethoxysilane.svg 3-(trimethoxysilyl)propane-1-thiol 3-Trimethoxysilyl-1-propanethiol 3-(trimethoxysilyl)propanethiol 3-(trimethoxysilyl)propane-1-thiol 4420-74-0 correct CAS 3185147 224-588-5 correct FDA 8CB1M08OIW 20473 19280 CO[Si](CCCS)(OC)OC 1S/C6H16O3SSi/c1-7-11(8-2,9-3)6-4-5-10/h10H,4-6H2,1-3H3 UUEWCQRISZBELL-UHFFFAOYSA-N 6 16 3 1 1 Colorless liquid with a stench 1.057 g/cm3 213 1.44 Insoluble but hydrolyzes/reacts over time Soluble in alcohols, ketones, aliphatic/aromatic hydrocarbons skin sensitization severe eye irritation harmful if swallowed 07 09 Warning 302 312 317 319 411 261 264 264+265 270 272 273 280 301+317 302+352 305+351+338 317 321 330 333+317 337+317 362+364 391 501 In polymer chemistry, (3-mercaptopropyl)trimethoxysilane (MPTMS) is a hybrid organic compound used as a monomer in organosilicon reactions. It consists of a central silicon core atom surrounded by three methoxy groups [-OCH3] and one mercaptopropyl [-C3H6SH] substituent groups. The center, silicon core allows for easy incorporation into organic and inorganic materials, and the thiol group allows for biocompatibility and excellent reactivity. Synthesis At an industrial scale, MPTMS is commonly synthesized through the thiolation of (3-chloropropyl)trimethoxysilane (CPTMS) with either sodium hydrosulfide (NaSH) or thiourea through biomolecular nucleophilic substitution.2026-04-22 2015-08-07 A Preparation Method for 3-Mercaptopropyltrimethoxysilane https://worldwide.espacenet.com/patent/search/family/054794301/publication/CN105153216A?q=pn%3DCN105153216A The multistep synthesis usually takes place in methanol over a period of 5–24 hours resulting in the thionation of the CPTMS chlorine atom with a sulfur atom.2026-04-22 2026 An In-depth Technical Guide to the Synthesis of (3-Mercaptopropyl)trimethoxysilane https://worldwide.espacenet.com/patent/search/family/037649491/publication/US2007060764A1?q=pn%3DUS2007060764 One of the possible methods is shown below: A faster avenue of synthesis, done in lab settings, involves adding CPTMS dropwise into dimethylformamide (DMF) solution containing NaSH and heating the solution at 110 °C for 45 minutes. Alternative synthesis routes include using phase transfer catalysts like benzyltributylammonium chloride (BTBAC)Can, W.; Jun, J.; Xin, W.; Shengyun, C.; Jun, G.; Shuguan, G. 种3-巯丙基三乙氧基硅烷偶联剂的制备 [A Preparation Method of 3-Mercaptopropyltriethoxysilane Coupling Agent]. using , 2013. or using UV photoinitiators like 2,2-dimethoxy-2-phenylacetophenone (DMPA) to drive the conversion. All methods require purification of crude MPTMS with vacuum filtration and the addition of a polymerization inhibitor to the solution. Polymerization procedures In polymerization chemistry, MPTMS monomers have two polymerization pathways to utilize. One pathway uses the core Si and the methoxy groups to react in sol-gel silanization creating a Si-O-Si siloxane backbone and allowing MPTMS to graft onto inorganic surfaces. Kawamura Midori Fudei T. Abe Y. March 2013 Growth of Ag thin films on glass substrates with a 3-mercaptopropyltrimethoxysilane (MPTMS) interlayer Journal of Physics: Conference Series 417 1 2004 10.1088/1742-6596/417/1/012004 2013JPhCS.417a2004K free These gel polymers may also link together creating partial silsesquioxane networks or full silsesquioxane cages.Silicon-Containing Polymers: The Science and Technology of Their Synthesis and Applications Kluwer Academic Publishers 2000 1st Dordrecht, The Netherlands 157–183 Jones, R. G. Ando, W. Chojnowski, J. 1-4020-0348-X The terminal sulfur on the mercaptopropyl group can be utilized as a bridge to other polymers, attach to surfaces, and can prepare nanocomposite materials via thiol-ene reactions. Karaca N. 30 June 2021 The synthesis and characterization of polyorganosiloxane nanoparticles from 3-mercaptopropyltrimethoxysilane for preparation of nanocomposite films via photoinitiated thiol-ene polymerization. Turk J Chem 45 3 761–774 10.3906/kim-2012-48 free 34385866 8326481 These polymerizations are often initiated with UV reactive photoinitiators that “click” the sulfur to a corresponding alkene. The terminal sulfur may also be left free to act as an anchor for nitric oxide or other medically relevant molecules. Hallowell Kyle D. Naser Aldine Fatima Vonder Brink Hope N. Vonder Mockensturm Ashley K. Handa Hitesh Brisbois Elizabeth J. Ostrowski Alexis D. Furgal Joseph C. Network Silsesquioxane-Based Organogel/Silicone Composites for the Long-Lasting Delivery of Nitric Oxide Molecules 2026 31 8 1343 10.3390/molecules31081343 free 42076020 13119455 Applications and uses MPTMS is commonly used in biosensing applications as a surface functionalization reagent, a component of multilayer interfaces for immobilization of biomolecules, and permselective membrane material. It is so versatile due to the thiol group that provides a reactive handle for surface attachment and the trimethoxysilane group that allows the formation of a stable silane-based film on an oxide or metal-supported surface. Ardoino Niccolò Lunelli Lorenzo Pucker Georg Vanzetti Lia Favaretto Rachele Pasquardini Laura Pederzolli Cecilia Guardiani Carlo Potrich Cristina Optimization of Surface Functionalizations for Ring Resonator-Based Biosensors Sensors 2024 24 10 3107 10.3390/s24103107 free 38793970 11124806 2024Senso..24.3107A Yang Yang-Li Tseng Ta-Feng Lou Shyh-Liang 2007 29th Annual International Conference of the IEEE Engineering in Medicine and Biology Society Using MPTMS as Permselective Membranes of Biosensors 2007 6624–6627 10.1109/IEMBS.2007.4353878 18003544 978-1-4244-0787-3 Shen Y. Wu T. Zhang Y. Li J. Comparison of two-typed (3-mercaptopropyl)trimethoxysilane-based networks on Au substrates Talanta 2005 65 2 481–488 10.1016/j.talanta.2004.06.030 18969823 In the use of a permselective membrane, MPTMS was attached to platinum electrodes and compared to Nafion as a protective layer. MPTMS’s inclusion inhibited interference from common electroactive species like ascorbic acid and uric acid while allowing the target analyte to be detected. A study showed that MPTMS-based electrodes produced significantly lower interference than the Nafion based ones. This is important in electrochemical sensors where background species can obscure the response. This same study showed that MPTMS can support a glucose biosensor. A platinum electrode was prepared with glucose oxidase, immobilized with polyaniline and modified by MPTMS which acted as a selective layer that improved that electrochemical environment. It was found that the applied potential of 0.4V gave the best signal generation with minimal interference. MPTMS can be used to produce thiol films that can be modified with aptamers or proteins. These films can help improve biosensing performance, which depends on the number of reacting groups, the stability of the coating, and how well the recognition elements are oriented for binding. With this, it can also serve as an anchor for coupling reactions. This is helpful when trying to measure proteins, antibodies, enzymes, and DNA which can be attached firmly to a surface using MPTMS as a link layer between the substrate and the biological recognition component. MPTMS is also being used to treat mesoporous silica to produce a material capable of removing heavy metals from aqueous and non aqueous waste as a stable and regeneratable material. Feng X. Fryxell G. E. Wang L.-Q. Kim A. Y. Liu J. Kemner K. M. Functionalized Monolayers on Ordered Mesoporous Supports Science 1997 276 5314 923–926 10.1126/science.276.5314.923 It is one of three components used in the process of forming thio-organosilica nanoparticles, Nakamura Michihiro Ishimura Kazunori One-Pot Synthesis and Characterization of Three Kinds of Thiol−Organosilica Nanoparticles Langmuir 2008 24 9 5099–5108 10.1021/la703395w 18366224 and it can modify glass substrates to speed up the process of depositing CdS films through successive ionic layer adsorption and reaction (SILAR). Sun Hua Mu Jin SILAR Deposition of CDS Thin Films on Glass Substrates Modified with 3-Mercaptopropyltrimethoxysilane Journal of Dispersion Science and Technology 2005 26 6 719–722 10.1081/DIS-200063026 References Category:Organosilicon compounds Category:Monomers Category:Thiols