Trimethylsilyl esters
Trimethylsilyl (TMS) esters are organosilicon compounds that serve as protective groups in organic synthesis. These esters are commonly used to protect hydroxyl groups from unwanted side reactions, such as dehydration or substitution reactions. The TMS group is highly stable and can be selectively removed under mild conditions using fluoride salts like tetra-n-butylammonium fluoride (TBAF) or hydrogen fluoride/pyridine (HF/pyr). This makes them particularly useful in multi-step synthetic sequences where hydroxyl groups need to remain intact. Trimethylsilyl esters are widely employed in pharmaceutical, polymer chemistry, and analytical chemistry applications due to their ease of synthesis and controlled reactivity.
These compounds can be synthesized from carboxylic acids through a straightforward reaction with trimethylsilyldiazomethane (TMS-CH2N2). Once the desired functional groups have been installed or modified, TMS esters are typically deprotected to regenerate the free hydroxyl group. The ability to selectively protect and then remove these protecting groups offers significant flexibility in organic synthesis strategies.
| Structure | Chemical Name | CAS | MF |
|---|---|---|---|
![]() |
Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate | 120801-75-4 | C5H9F3O4SSi |
![]() |
Trimethylsilyl bromoacetate | 18291-80-0 | C5H11BrO2Si |
![]() |
Trimethylsilyl acrylate | 13688-55-6 | C6H12O2Si |
![]() |
METHYL TRIMETHYLSILYL MALONATE | 51849-23-1 | C7H14O4Si |
![]() |
Bis(trimethylsilyl) malonate | 18457-04-0 | C9H20O4Si2 |
![]() |
Benzeneacetic acid,trimethylsilyl ester | 2078-18-4 | C11H16O2Si |
![]() |
2-Butynedioic acid,1,4-bis(trimethylsilyl) ester | 76734-92-4 | C10H18O4Si2 |
![]() |
Trimethylsilyl Methacrylate | 13688-56-7 | C7H14O2Si |
![]() |
2-Butenoic acid,4-(trimethylsilyl)-, trimethylsilyl ester, (2E)- | 109751-81-7 | C10H22O2Si2 |
![]() |
Hexadecanoic acid, trimethylsilyl ester | 55520-89-3 | C19H40O2Si |
Related Literature
-
Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
-
Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
-
Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849
-
Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
-
Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
Recommended suppliers
-
Shandong Feiyang Chemical Co., LtdFactory Trade Brand reagentsCompany nature: Private enterprises
-
Shaanxi pure crystal photoelectric technology co. LTDFactory Trade Brand reagentsCompany nature: Private enterprises
-
Suzhou Senfeida Chemical Co., LtdFactory Trade Brand reagentsCompany nature: Private enterprises
-
Shanghai Pearlk Chemicals Co., Ltd.Factory Trade Brand reagentsCompany nature: Private enterprises
-
Wuhan Comings Biotechnology Co., Ltd.Factory Trade Brand reagentsCompany nature: Private enterprises
Recommended products









