4131-47-9

Basic information

• Product Name: Acetylene, 1-phenyl-2-trimethylgermyl-
• Synonyms: Acetylene, 1-phenyl-2-trimethylgermyl-
• CAS NO: 4131-47-9
• Molecular Formula: C₁₁H₁₄Ge
• Molecular Weight: 0
• Mol File: 4131-47-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 231.9°C at 760 mmHg
• Flash Point: 85.5°C
• Appearance: /
• Vapor Pressure: 0.0924mmHg at 25°C
• CAS DataBase Reference: Acetylene, 1-phenyl-2-trimethylgermyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetylene, 1-phenyl-2-trimethylgermyl-(4131-47-9)
• EPA Substance Registry System: Acetylene, 1-phenyl-2-trimethylgermyl-(4131-47-9)

Safety Data

• Hazardous Substances Data: 4131-47-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14Ge/c1-12(2,3)10-9-11-7-5-4-6-8-11/h4-8H,1-3H3

Upstream product

• 126086-83-7 C₆H₅C₂Ge(CH₃)2Br 
• 1066-38-2 iodotrimethylgermane 
• 536-74-3 phenylacetylene 
• 2290-59-7 1-trimethylsilyl-2-trimethylgermylacetylene 

Downstream Products

• 339576-91-9 (E)-4-[1-(trimethylgermyl)benzylidene]-3-borahomoadamantane 

Relevant articles and documents

Iridium complex catalyzed germylative coupling reaction between alkynes and iodogermanes-a new route to alkynylgermanium and alkynylgermasilicon compounds

The new reaction of terminal alkynes with iodogermanes proceeding in the presence of an IrI-complex [{Ir(μ-Cl)(CO)2}2] (I) and NEt(iPr)2, as a hydrogen iodide acceptor, leads to the formation of functionalized alkynylgermanes. This reaction occurs via direct activation of the Csp-H bond in the starting alkyne. Detailed stoichiometric experiments using [Ir(cod)(CCPh)(PCy3)] (IVa) and iodogermane were performed and resulted in a proposal of a reasonable mechanism for the germylative coupling reaction between alkynes and iodogermanes.

Chemie der schweren Carben-Analogen R2M, M=Si, Ge, Sn XIII. Reaktionen von thermisch und photolytisch erzeugtem Dimethylgermylen mit Alkinyl, Propargyl- und Allenyl- halogeniden, sowie Aktivierungsparameter der Germylenbildung

Free Me2Ge (1) inserts efficiently into C-Cl and C-Br bonds of alkynyl halides (3) and propargyl halides (6) under thermal or under photolytica conditions and prefers a concerted mechanism.In addition to the expected propargyl germyl derivatives (7), the rearranged allenyl derivatives (8) are also found.With other propargyl halides (9), the rearranged products 1-(halogenodimethylgermyl)allenes (10) are formed almost exclusively.Allenyl bromides (12) quantitatively yield the expected insertion products, 1-(bromodimethylgermyl)allenes (13).The mechanisms are discussed.The rates of all the thermal reactions equivalent to the spontaneous first order decay of the Me2Ge precursor, 7-dimethylgerma-2,3-benzonorbornadiene (2).EA of the thermolysis is 28.1+/-1.0, ΔH=27.4+/-1.0, ΔG=26.7+/-1.6 kcal/mol, ΔS=6.1+/-1.6 e.u. (58-80 degC, 0.05-0.21 M solutions), in benzene or in Ph2O.Addition of excess CCl4, CCl3Br, and tBuCCCN, all of which react rapidly with 1, have no influence on these values.The intermediate adduct of 1 to alkyne, V12., the germirene (15), was not detected; 1,4-digermacyclohexadiene (16) is the first, and only product to be observed.