17881-95-7

Basic information

• Product Name: 3-(triMethylsilyl)phenol
• Synonyms: 3-(triMethylsilyl)phenol
• CAS NO: 17881-95-7
• Molecular Formula: C₉H₁₄OSi
• Molecular Weight: 166.29236
• Mol File: 17881-95-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 216.6°Cat760mmHg
• Flash Point: 84.8°C
• Appearance: /
• Density: 0.96g/cm³
• Vapor Pressure: 0.0944mmHg at 25°C
• Refractive Index: 1.503
• PKA: 10.15±0.10(Predicted)
• CAS DataBase Reference: 3-(triMethylsilyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(triMethylsilyl)phenol(17881-95-7)
• EPA Substance Registry System: 3-(triMethylsilyl)phenol(17881-95-7)

Safety Data

• Hazardous Substances Data: 17881-95-7(Hazardous Substances Data)

Usage

General Description

3-(trimethylsilyl)phenol is a chemical compound also known as TMS phenol, with the molecular formula C9H14OSi. It is a derivative of phenol with a trimethylsilyl group attached to the aromatic ring. 3-(triMethylsilyl)phenol is often used as a protecting group in organic synthesis to temporarily block the reactivity of phenolic hydroxyl groups. It is a colorless liquid with a boiling point of 148-150°C and is typically stable under normal conditions. 3-(trimethylsilyl)phenol is widely utilized in research and industrial processes as a versatile reagent in organic chemistry, particularly in the protection and deprotection of hydroxyl groups.

InChI:InChI=1/C9H14OSi/c1-11(2,3)9-6-4-5-8(10)7-9/h4-7,10H,1-3H3

Upstream product

• 18036-82-3 3-trimethylsilyphenyl trimethylsilyl ether 
• 75-77-4 chloro-trimethyl-silane 
• 591-20-8 3-Bromophenol 
• 17881-67-3 (3-chlorophenoxy)triisopropylsilane 
• 1004322-73-9 4-chloro-3-trimethylsilanylphenol 
• 75-89-8 2,2,2-trifluoroethanol 

Downstream Products

• 18001-12-2 m-(Trimethylsilyl)phenyl Acetate 
• 497180-94-6 O-(3-trimethylsilylphenyl)-N,N-dimethylaminothiocarbamate 
• 17881-83-3 3-trimethylsilylbenzenethiol 
• 497180-97-9 S-(3-trimethylsilylphenyl)-N,N-dimethylaminothiocarbamate 
• 126485-61-8 (3-Trimethylsilanyl-phenoxy)-acetic acid 
• 126485-68-5 N-(2-Dimethylamino-ethyl)-2-(3-trimethylsilanyl-phenoxy)-acetamide 
• 126485-63-0 (3-Trimethylsilanyl-phenoxy)-acetic acid 2-dimethylamino-ethyl ester 
• 126485-75-4 (3-Iodo-phenoxy)-acetic acid 2-dimethylamino-ethyl ester; hydrochloride 
• 126485-80-1 N-(2-Dimethylamino-ethyl)-2-(3-iodo-phenoxy)-acetamide; hydrochloride 
• 35065-86-2 3-bromophenyl acetate 
• 42861-71-2 3-iodophenylacetate 

Relevant articles and documents

Highly enantioselective (-)-sparteine-mediated lateral metalation-functionalization of remote silyl protected ortho -ethyl N, N -dialkyl aryl O -carbamates

We report the enantioselective, lateral deprotonation of ortho-protected or functionalized tertiary N,N-dialkyl aryl O-carbamates 5-7 (Scheme 2) and meta-protected carbamates 14, 15, and 20 (Schemes 5 and 7) by s-BuLi/(-)-sparteine and subsequent quench w

Expanding the Chemical Space of Succinate Dehydrogenase Inhibitors via the Carbon-Silicon Switch Strategy

The carbon-silicon switch strategy has become a key technique for structural optimization of drugs to widen the chemical space, increase drug activity against targeted proteins, and generate novel and patentable lead compounds. Flubeneteram, targeting succinate dehydrogenase (SDH), is a promising fungicide candidate recently developed in China. We describe the synthesis of novel SDH inhibitors with enhanced fungicidal activity to enlarge the chemical space of flubeneteram by employing the C-Si switch strategy. Several of the thus formed flubeneteram-silyl derivatives exhibited improved fungicidal activity against porcine SDH compared with the lead compound flubeneteram and the positive controls. Disease control experiments conducted in a greenhouse showed that trimethyl-silyl-substituted compound W2 showed comparable and even higher fungicidal activities compared to benzovindiflupyr and flubeneteram, respectively, even with a low concentration of 0.19 mg/L for soybean rust control. Furthermore, compound W2 encouragingly performed slightly better control than azoxystrobin and was less active than benzovindiflupyr at the concentration of 100 mg/L against soybean rust in field trials. The computational results showed that the silyl-substituted phenyl moiety in W2 could form strong van der Waals (VDW) interactions with SDH. Our results indicate that the C-Si switch strategy is an effective method for the development of novel SDH inhibitors.

The β effect of silicon in phenyl cations

Irradiation of chloroanisoles, phenols, and N,N-dimethylanilines bearing a trimethylsilyl (TMS) group in the ortho position with respect to the chlorine atom caused photoheterolysis of the Ar-Cl bond and formation of the corresponding ortho-trimethylsilylphenyl cations in the triplet state. The β effect of silicon on these intermediates has been studied by comparing the resulting chemistry in alcoholic solvents with that of the silicon-free analogues and by computational analysis (at the UB3LYP/6-311+G(2d,p) level in MeOH). TMS groups little affect the photophysics and the photocleavage of the starting phenyl chlorides, while stabilizing the phenyl cations, both in the triplet (ca. 4 kcal/mol per group) and, dramatically, in the singlet state (9 kcal/mol). As a result, although triplet phenyl cations are the first formed species, intersystem crossing to the more stable singlets is favored with chloroanisoles and phenols. Indeed, with these compounds, solvent addition to give aryl ethers (from the singlet) competed efficiently with reduction or arylation (from the triplet). In the case of the silylated 4-chloro-N,N- dimethylaniline, the triplet cation remained in the ground state and trapping by π nucleophiles remained efficient, though slowed by the steric bulk of the TMS group. In alcohols, the silyl group was eliminated via a photoinduced protiodesilylation during the irradiation. Thus, the silyl group could be considered as a directing, photoremovable group that allowed shifting to the singlet phenyl cation chemistry and was smoothly eliminated in the same one-pot procedure.