38858-72-9

Basic information

• Product Name: (3 4-DIHYDRO-1-NAPHTHYLOXY)TRIMETHYL-
• Synonyms: (3 4-DIHYDRO-1-NAPHTHYLOXY)TRIMETHYL-;(3,4-DIHYDRO-1-NAPHTHYLOXY)TRIMETHYL-SIL;(3,4-Dihydro-1-naphthyloxy)trimethylsilane 97%
• CAS NO: 38858-72-9
• Molecular Formula: C₁₃H₁₈OSi
• Molecular Weight: 218.37
• Product Categories: Organic Building Blocks;Oxygen Compounds;Protected Alcohols/Phenols
• Mol File: 38858-72-9.mol
• Article Data: 46

Chemical Properties

• Boiling Point: 63-65 °C0.01 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.983 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: n20/D 1.5287(lit.)
• CAS DataBase Reference: (3 4-DIHYDRO-1-NAPHTHYLOXY)TRIMETHYL-(CAS DataBase Reference)
• NIST Chemistry Reference: (3 4-DIHYDRO-1-NAPHTHYLOXY)TRIMETHYL-(38858-72-9)
• EPA Substance Registry System: (3 4-DIHYDRO-1-NAPHTHYLOXY)TRIMETHYL-(38858-72-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 38858-72-9(Hazardous Substances Data)

Usage

General Description

(3,4-Dihydro-1-naphthyloxy)trimethylsilane (3,4-dihydronaphthalen-1-yloxy(trimethyl)silane) is a protected phenol. Its IR spectral analysis suggests νmax (DCM) = 1638cm-1.

InChI:InChI=1/C13H18OSi/c1-15(2,3)14-13-10-6-8-11-7-4-5-9-12(11)13/h4-5,7,9-10H,6,8H2,1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 19369-49-4 naphthalene-1(4H)-one 
• 2754-27-0 trimethylsilyl acetate 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1821-12-1 4-Phenylbutyric acid 
• 2051-95-8 succinylbenzene 
• 71-43-2 benzene 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 103817-03-4 1-<(trimethylsilyl)methyl>-1,2,4-triazole 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 7498-87-5 2-phenyl-3,4-dihydro-2H-naphthalen-1-one 
• 6202-48-8 trimethyl(1-naphthaleneoxy)silane 
• 19579-63-6 3-hydroxy-3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)indolin-2-one 
• 54669-72-6 2-(2-oxo-2-phenylethyl)-3,4-dihydronaphthalen-1(2H)-one 

Relevant articles and documents

Reactions of gem-Difluorinated Phosphonium Salts Induced by Light

gem-Difluorinated phosphonium salts, which are readily obtained from aldehydes and difluoromethylene phosphobetaine, can serve as a source of radicals under reductive conditions. An iridium complex or Hantzsch ester was used as a one-electron reducing agent when irradiated with visible light. The fluorinated radicals were trapped with various alkenes, leading to products either via a photoredox cycle (for the iridium catalyst) or via a hydrogen atom transfer (for the Hantzsch ester).

Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis

We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.

The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp3)-O Arylation

The ability to understand and predict reactivity is essential for the development of new reactions. In the context of Ni-catalyzed C(sp3)-O functionalization, we have developed a unique strategy employing activated cyclopropanols to aid the design and optimization of a redox-active leaving group for C(sp3)-O arylation. In this chemistry, the cyclopropane ring acts as a reporter of leaving-group reactivity, since the ring-opened product is obtained under polar (2e) conditions, and the ring-closed product is obtained under radical (1e) conditions. Mechanistic studies demonstrate that the optimal leaving group is redox-active and are consistent with a Ni(I)/Ni(III) catalytic cycle. The optimized reaction conditions are also used to synthesize a number of arylcyclopropanes, which are valuable pharmaceutical motifs.