2816-43-5

Basic information

• Product Name: TRIPHENYLGERMANE
• Synonyms: GERMANIUM TRIPHENYL;TRIPHENYLGERMANIUM HYDRIDE;TRIPHENYLGERMANE;TRIPHENYL GERMANIUM;Triphenylgermanyl hydride
• CAS NO: 2816-43-5
• Molecular Formula: C18H16Ge
• Molecular Weight: 304.96
• EINECS: 220-569-0
• Product Categories: GermaniumSynthetic Reagents;Metal HydridesOrganometallic Reagents;Organogermanium;Others;Precursors by Metal;Reduction;Vapor Deposition Precursors;Chemical Synthesis;CVD and ALD Precursors by Metal;Germanium;Materials Science;Metal Hydrides;Micro/NanoElectronics;Organometallic Reagents;Synthetic Reagents;Vapor Deposition Precursors
• Mol File: 2816-43-5.mol
• Article Data: 29

Chemical Properties

• Melting Point: 40-43 °C(lit.)
• Boiling Point: 128-9°C 0,03mm
• Flash Point: >110°C
• Appearance: /
• Refractive Index: 1.6187
• CAS DataBase Reference: TRIPHENYLGERMANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPHENYLGERMANE(2816-43-5)
• EPA Substance Registry System: TRIPHENYLGERMANE(2816-43-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 2816-43-5(Hazardous Substances Data)

Usage

Description

Triphenylgermanium, also known as triphenylgermane, is an organogermanium compound with the chemical formula (C6H5)3GeH. It is a colorless, crystalline solid that is sensitive to air and moisture. Triphenylgermanium is known for its ability to act as a hydrogen donor and readily adds to terminal acetylenes and olefins.

Uses

Used in Chemical Synthesis:
Triphenylgermanium is used as a hydrogen donor in various chemical reactions, facilitating the transfer of hydrogen atoms to other molecules. This property makes it a valuable reagent in the synthesis of various organic compounds.
Used in the Isomerization of (Z) Alkene:
Triphenylgermanium is employed in the isomerization process of (Z) alkenes, where it aids in the conversion of (Z) alkenes to their (E) isomers. This isomerization is crucial in the production of specific compounds with desired properties.
Used in the Formation of Germyl Radicals:
Triphenylgermanium reacts with TEMPO (2,2,6,6-Tetramethylpiperidinyloxy) to form its corresponding germyl radical. This reaction is significant in various chemical processes that require the generation of germyl radicals for further reactions.
Used in Reductive Alkylation:
Triphenylgermanium is used in the reductive alkylation of acrylonitrile and enones. This application is essential in the synthesis of various nitrogen-containing compounds and cyclic structures, which are vital in the pharmaceutical and chemical industries.
Used in the Pharmaceutical Industry:
In the pharmaceutical industry, triphenylgermanium may be utilized as a reagent in the synthesis of complex organic molecules, including potential drug candidates. Its ability to act as a hydrogen donor and participate in various chemical reactions makes it a valuable tool in drug development.
Used in the Chemical Research Industry:
Triphenylgermanium is also used in the chemical research industry for studying the properties and reactivity of organogermanium compounds. Its unique characteristics and applications in various chemical reactions make it an interesting subject for research and development.

InChI:InChI=1/C18H15Ge/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

Upstream product

• 3005-32-1 triphenylgermanium bromide 
• 591-51-5 phenyllithium 
• 6031-52-3 (C₆H₅)3Ge*Sn(CH₃)3 
• 7726-95-6 bromine 
• 16853-85-3 lithium aluminium tetrahydride 
• 112712-64-8 tris(1,2-benzenediolato-O,O′)germanate 
• 1626-24-0 chlorotriphenylgermane 
• 1613-66-7 dichlorodiphenylgermane 
• 120154-50-9 trimesitylgermyllithium 
• 24973-59-9 2,4,6-tri-tert-butyl-1-nitrosobenzene 
• 3839-32-5 triphenyl germyllithium 
• 75-65-0 tert-butyl alcohol 
• 379-47-5 triphenylgermanium fluoride 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 18479-38-4 Hexyl-triphenyl-german 
• 116488-03-0 (Z)-6-triphenylgermyl-6-dodecene 
• 114566-81-3 (E)-6-triphenylgermyl-6-dodecene 
• 116488-01-8 (Z)-6-Triphenylgermanyl-hex-5-en-1-ol 
• 116488-02-9 (E)-6-Triphenylgermanyl-hex-5-en-1-ol 
• 116487-94-6 (Z)-1-triphenylgermyl-1-dodecene 
• 92740-99-3 (E)-1-triphenylgermyl-1-dodecene 
• 726-18-1 4,4'-dianisylmethane 
• 139599-12-5 triphenylgermanetriflate 
• 73829-51-3 3-Triphenylgermanyl-propionamide 
• 73829-52-4 3-Triphenylgermanyl-propylamine 
• 116524-24-4 (Z)-4-triphenylgermyl-3-buten-1-ol 
• 114566-79-9 (E)-4-triphenylgermyl-3-buten-1-ol 
• 116385-49-0 (Z)-1-triphenylgermyl-1-propene 

Relevant articles and documents

Donor-acceptor molecular oligogermanes: Novel properties and structural aspects

The linear oligogermyl amide 2, Ph3GeGeMe2NMe2, was obtained by reacting Ph3GeLi with 1, Me2Ge(Cl)NMe2. The amide 2 was used for the synthesis of molecular oligogermanes 3, Ph3GeGeMe2Ge(C6F5)3, and 4, [Ph3GeGeMe2]2Ge(C6F5)2, containing electron donor (Me, Ph) and acceptor (C6F5) groups, by using a hydrogermolysis reaction in n-hexane. The molecular structures of 3 and 4 were studied by XRD. It was shown that in a crystal 3 forms wide channels, in which the solvated nonpolar n-hexane molecule is present. The NMR (1H, 13C and 19F), optical (UV/vis absorption, luminescence) and electrochemical (cyclic voltammetry) properties of both compounds were also studied. The impact of the substitution type by the electron withdrawing groups (at the terminal position, such as in 3, or within the compound, such as in 5), on the physical properties was also studied.

THE INTERACTION OF NICKELOCENE WITH BIS(TRIPHENYLGERMYL)CADMIUM

The reaction of bis(triphenylgermyl)cadmium with nickelocene proceeds through the displacement of a cyclopentadienyl ring and the formation of an organopolymetallic compound containing nine metal atoms: This is a new type of organometallic compound, containing Ni-Cd bonds.

Photodecompostion of the Oligogermanes nBu3GeGePh2GenBu3 and nBu3GeGePh3: Identification of the Photoproducts by Spectroscopic and Spectrometric Methods

The oligogermane nBu3GeGePh2GenBu3was photolyzed using UV-C light in the presence of acetic acid as a trapping agent and the photoproducts were identified using1H NMR spectroscopy, gas chromatography/electron-impact mass spectrometry, and high resolution accurate mass mass spectrometry. The products identified were the germanes nBu3GeH, nBu3GeOAc, and Ph2Ge(H)OAc (OAc = C2H3O2) and the digermane nBu6Ge2. This indicates that both germanium–germanium single bonds are cleaved homolytically upon irradiation to generate two nBu3Ge·radicals and the germylene Ph2Ge:. The digermane nBu3GeGePh3was also photolyzed under identical conditions, and in this case the photoproducts were identified as nBu3GeH, nBu3GeOAc, Ph3GeH, Ph3GeOAc and the digermanes nBu6Ge2and Ph6Ge2.

Syntheses and characterization of organo-group 14 cobaloxime compounds

Reactions of cobaloxime Na[(t-BuPy)Co(DH)2] with Ph 3ECl (E = Si, Ge, Sn, and Pb) were investigated. Metal-metal bonded complexes (t-BuPy)Co(DH)2EPh3 were isolated for E = Sn and Pb. (f-BuPy)Co(DH)2SnPh3·(C2H 5)2O, C39H52CoN5O 5Sn, crystallized in the monoclinic space group P21/c (Z = 4) with unit cell dimensions a = 11.6443-(6) A, b = 15.6085(8) A, c = 22.6354(12) A, β = 96.634(1)°, and V= 4086.4(4) A3 at 295(2) K. The structure resembled those of six-coordinate alkyl cobaloxime complexes and had Co-NPy and Co-Sn distances of 2.056(2) and 2.5568(3) A, respectively. (t-BuPy)Co(DH) 2PbPh3, C35H42CoN5O 4Pb, crystallized in the monoclinic space group P21/n (Z = 4) with unit cell dimensions a = 15.0104(7) A, b = 15.7693(8) A, c = 16.6230(8) A, β = 114.348(1)°, and V = 3584.8(3) A3 at 295(2) K. The complex was nearly isostructural with the Sn analogue and had Co-NPy and Co-Pb distances of 2.049(2) and 2.6191(4) A, respectively. Coupling of the ortho phenyl protons to the spin 1/2 isotopes of Sn and of Pb was a characteristic feature of the 1H NMR spectrum. Additional, longer range couplings were observed for the Pb complex and for both complexes in the 13C NMR. Metal-metal bonded complexes were not obtained for E = Si or Ge. The products isolated in the latter case were the hydride Ph3GeH and the cobalt(II) complex (t-BuPy)Co(DH)2,C17H27CoN5O 4, which crystallized in the orthorhombic space group Pbcn (Z = 8). Unit cell dimensions were a = 17.9821(11) A, b = 9.7449(6) A, c = 22.7374(15) A, and V = 3984.4(4) A3 at 295(2) K. The five-coordinate complex had Co-NPy = 2.096(2) A and was dimeric in the lattice.