3246-98-8

Basic information

• Product Name: benzyl(triphenyl)germane
• CAS NO: 3246-98-8
• Molecular Formula: C₂₅H₂₂Ge
• Molecular Weight: 395.0822
• Mol File: 3246-98-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 484.1°C at 760 mmHg
• Flash Point: 246.3°C
• Vapor Pressure: 4.68E-09mmHg at 25°C
• CAS DataBase Reference: benzyl(triphenyl)germane(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl(triphenyl)germane(3246-98-8)
• EPA Substance Registry System: benzyl(triphenyl)germane(3246-98-8)

Safety Data

• Hazardous Substances Data: 3246-98-8(Hazardous Substances Data)

Usage

Description

Benzyl(triphenyl)germane, with the chemical formula C6H5CH2GePh3, is an organogermanium compound that serves as a reagent in organic synthesis. It is a colorless liquid with a faint odor and is insoluble in water. benzyl(triphenyl)germane is recognized for its capacity to perform hydrogermylation reactions, which is the addition of a germyl group to carbon-carbon multiple bonds. It is also utilized in the production of organogermanium polymers and as a precursor to other organogermanium compounds. Benzyl(triphenyl)germane is considered to be a relatively stable and safe compound.

Uses

Used in Organic Synthesis:
Benzyl(triphenyl)germane is used as a reagent for hydrogermylation reactions, which is crucial for the addition of a germyl group to carbon-carbon multiple bonds. This application is significant in the synthesis of various organic compounds.
Used in Polymer Production:
benzyl(triphenyl)germane is utilized in the production of organogermanium polymers, contributing to the development of materials with unique properties for various applications.
Used as a Precursor:
Benzyl(triphenyl)germane serves as a precursor to other organogermanium compounds, playing a vital role in the synthesis of a range of germanium-based materials for different industries.

Upstream product

• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 3839-32-5 triphenyl germyllithium 
• 1626-24-0 chlorotriphenylgermane 
• 34422-60-1 triphenylgermylsodium 
• 105028-41-9 (α-phenylacetyl)triphenylgermane 

Relevant articles and documents

Mechanistic Dichotomy of Magnesium- and Zinc-Based Germanium Nucleophiles in the C(sp3)?Ge Cross-Coupling with Alkyl Electrophiles

Robust procedures for two mechanistically distinct C(sp3)?Ge bond formations from alkyl electrophiles and germanium nucleophiles are reported. The germanium reagents were made available as bench-stable solutions by lithium-to-magnesium and lithium-to-zinc transmetalation, respectively. The germanium Grignard reagent reacts with various primary and secondary alkyl electrophiles by an ionic nucleophilic displacement. Conversely, the coupling of the corresponding zinc reagent requires a nickel catalyst, which then engages in radical bond formations with primary, secondary, and even tertiary alkyl bromides. Both methods avoid the regioselectivity issue of alkene hydrogermylation and enable the synthesis of a wide range of functionalized alkyl-substituted germanes.

Stannyl-Lithium: A Facile and Efficient Synthesis Facilitating Further Applications

We have developed a highly efficient, practical, polycyclic aromatic hydrocarbon (PAH)-catalyzed synthesis of stannyl lithium (Sn-Li), in which the tin resource (stannyl chloride or distannyl) is rapidly and quantitatively transformed into Sn-Li reagent at room temperature without formation of any (toxic) byproducts. The resulting Sn-Li reagent can be stored at ambient temperature for months and shows high reactivity toward various substrates, with quantitative atom efficiency.

Photochemical Decarbonylation of (α-Arylacyl)triphenylgermane

(α-Arylacyl)triphenylgermanes were prepared from the corresponding esters with triphenylgermyllithium at room temperature in good yields.Photochemical decarbonylation of (α-arylacyl)triphenylgermanes took place under UV irradiation to quantitatively give